You know what’s worse than an embarrassing moment? An embarrassing moment when it involves a crush. Whether you’re the admirer or the admiree, there’s something about the vulnerability of having a crush that leads to the most awkward experiences in existence. These Redditors came together to share their stories about moments when their crushes went wrong—and they’re unforgettably brutal.
1. Flatulence Failure
I was 12 years old, hanging out at my friend’s for the night. His sister also had a girlfriend spending the night. They were hanging in the sister’s bedroom and we were playing video games in the den. I thought it would be funny to crack the bedroom door and moon them. Their backs were turned from the door, and after 10 seconds or so with them not noticing I thought it’d be funny to rip a stinky one to get their attention. Bending over in the middle of the doorway, pushed one out. Pooping.
2. The Long and Winding Road
When I was 17 years old, this girl that I was madly in love with asked me to drive her to Buffalo (a city 400 miles away from my hometown) to visit a friend. We had just kissed for the first time the week before, and I was elated to spend a weekend away with her. So I lied to my parents, drove all the way up to Buffalo in the dead of winter, and when we arrived at her friend’s house, another guy came out and gave her a hug and a kiss.
Not knowing what to do, I said, “Give me a call when you’re done.” I drove off to the mall, watched The Ice Harvest, slept in my car, and picked her up the next morning. I drove for 8 hours not saying a word, and listened to her try to apologize. To this day, I remain constantly paranoid that every subsequent woman I am with will do the same to me.
I still cringe when I think about it. I had a huge crush on this girl, thought she was really cool and I loved her art and I couldn’t believe she said yes. We went to the zoo because it was free and we were just broke teenagers and we had a blast. Afterward, we went to grab some food at this place before having to split off to go home. Our trains were heading in the opposite directions and the entrances were across the street from each other, so I walked with her to her side to say goodbye.
I closed my eyes and awkwardly leaned in to give her a kiss goodbye, and she went in more for a hug. I ended up headbutting her in the face and her nose started bleeding. I was so embarrassed and didn’t know what to say, so I just asked, “Are you okay?” She replied, “I think so.” Still not knowing what to do I just said, “Okay, bye!” and then ran across the street to catch my train.
4. Meeting the Family
My cousin once had a crush on me. She was two years younger than me and she saw something in a movie where the girl surprises the guy by waiting and lying naked in his bed. When I was 20, I was coming home where I live with my grandmother. My cousin came to my grandma’s house and waited on my bed wearing only her underwear and nothing on the top. Pretty bad right? No—this story is so much worse.
My grandmother failed to mention to her that I was bringing my college girlfriend for the weekend. As I was unloading the car, my grandmother offered to show my girlfriend to the room where she was going to be sleeping. But when they opened the door, they found my cousin who started screaming profusely.
5. Diving Right in
Me, 15-16, gets an invite from a mutual friend to a pool party. See old friends, make new acquaintances, and there she is. The girl I had a major crush on. She smiles and waves and continues floating around on her back. Attempt to dive over her, like a boss, and end up kneeing her right in the nose. There’s blood, screaming, and a hundred seething fingers pointed right at my feels. She ran away crying, and I never spoke to her again. I ended up seeing her about a week later, it was bad. I still feel terrible.
6. Cull the Herd (From Your Love Life)
This guy was academic, hygienic, and sweet. Treated waitstaff appropriately. Spoke formally but still funny. Shared things in common with me. Perfect gentleman. The date ended 10/10. While driving me home, at a stoplight, he pointed to a homeless man crossing the street and said something that made my jaw drop right to the floor.
He told me: “I would stop my car for anybody crossing the street, just not homeless men. Where do they have to be? They’re in no hurry.” Then he added another comment, saying “It’d be funny if I ran him over.”
7. The Conclusive Clap
I had an awkward “will they won’t they thing” with this lady for like two years. She was an awkward and shy type of girl in that really endearing way. I was into her but never realized she was into me so I never made a move. She was shy and never made a move. We both were in and out of relationships over this period also, we were never single at the same time so there was never any momentum to get together.
It was just one of those things, you’re into someone, nothing comes of it, you move on. She lived with a friend of mine at the time in a house share. One night I was drinking with my mate watching movies and she decided to join us, which happened occasionally, only this time she was single and I’d recently—literally a week earlier—become single.
Two years of pent-up-emotion-why-has-this-not-happened-before relations happened that night. Next morning, while still in her bedroom, I got the worst phone call of my life. My ex called me to advise she had chlamydia and I should go get tested to be safe. Naturally, I was obliged to pass on that message and completely crush this poor girl in doing so. It still makes me cringe a decade later.
8. Spring Off
I was on a date with a woman, and we really seemed to have the same interests. She was cool, a bit loud, and boisterous, which I happen to like. About a half hour in, she told me she needed to tell me something because she was really enjoying herself. What she had to tell me was that she had two sons under eight years old.
That in itself wasn’t the problem. Her next words were so cruel. She followed it with, “Don’t worry though. They live with their dad. I usually only have them one weekend a month. They won’t get in the way of anything.” It was such a casual dismissal of her own children. As somebody who does eventually want children, that was pretty much it for me.
9. Hearse, Don’t It?
I tried to impress a girl by attempting to razor scooter down the steepest hill around. Instead, I crashed into the back of a funeral hearse and shattered its back window. There was a dead body inside on its way to the cemetery. The deceased’s family was there waiting to take the coffin out. I was covered in blood and glass. I got up, grabbed my scooter, and hobbled away to the nearest alleyway without even pausing to process what had happened. Girl was not impressed…
10. How Can This Possibly Go Wrong?
Middle school. Cute Guy was overheard saying that he was impressed because a girl he knew had passed gas out loud and, not only did she not die of embarrassment, she just laughed it off. He thought that this was really cool because it showed she was secure and full of confidence. My friend had a crush on this guy and got it in her head that she needed to impress him, too.
We all tried to talk her out of it, but she was determined. She basically sat near him as often as possible for several days, trying to constantly pass gas and act like it was no big deal. Shockingly, he was not impressed, they did not date, and they are not celebrating any major milestone anniversaries later this year.
11. Beauty and the Beast
A coworker at work had just beautiful energy, absolutely lovely to be around. Always smiling at everyone, and she would laugh at my jokes, and she made some comments from time to time that made me feel validated and understood, which was very, very flattering. Like, she guessed my passions in life and told them to me, with a big smile while looking me in the eyes.
I’m a reserved guy who doesn’t share that stuff. All just very lovely. One day we’re in the break room and she’s talking to another guy the same way and I’m consciously talking myself out of being jealous: “You’re not dating or anything you don’t even have her cell phone number. She’s allowed to be lovely with other people now come on no reason to be jealous!”
Then when the guy leaves, she turns to the girl next to her and says, “God, I hate that guy.” And I had JUST been jealous that she was treating him exactly like she treats me. I still feel foolish when I think about it, like does she like me or hate me?
12. Chocolate Chip Fire
When I was 16, I was hanging out with a cute girl who I really liked. We’d been hanging out for about a month or two. At her house one night, I decided to do some impressing and announced that I would cook her and her mom dinner. I decided to make a surprise dessert of chocolate chip cookies with it, and put them in the oven right as we were sitting down to eat so they’d be ready once we finished eating.
It went great, my mom had taught me well and the dinner was delicious. Afterward, she and I were upstairs having a good time (in our underpants) when all of a sudden, her mom comes up yelling “FIRE!! WE’VE GOT TO GET OUT, THERE’S A FIRE!” We jump out of bed and run outside, still in our underpants, as the volunteer fire truck shows up.
Turns out it was just a smoke scare. I hadn’t set a timer because the cookies were going to be a surprise and I ended up forgetting about them. Ugh.
13. Clean Up On Aisle Love
It was high school, and I had a crush on a girl. I couldn’t stop thinking about her. I went to the birthday party of a friend’s friend partly because I knew she would be there. This could have been my chance at an overnight, mixed-gender birthday party at a kid’s huge house in the woods with maybe even a romantic fire.
I felt my opportunity was near when we were all gathered around the fire after hours of partying. We were all probably going to pack it in soon. But first, a little puff, puff pass. She didn’t react well to that. For starters, she got really dopey really fast. Then, she pooped her pants. I don’t mean it as a euphemism.
She was giggling excessively. Then there was some loud stomach gurgling. Then there was an incredibly loud toot. Then she laughed harder and said, “Oh my God! I pooped my pants!” She then laughed harder to the point of tears. After she stopped laughing, she wandered into the room where some folks were already sleeping.
She flopped onto her sleeping bag and passed out still with a load in her pants. As if this wasn’t enough to eliminate my interest, she woke up the next morning and spent an hour getting breakfast, drinking coffee, and doing other stuff before she decided to clean herself up. Lastly was where she left her dirty undies.
She just dumped it in the little garbage can next to the sink in the bathroom that most of us were using. So, I was trying to grab a shower next to that. My interest was officially rescinded.
14. Peeping Tom
When I was 9 or 10 years old, I had a huge crush on a boy in my class. We played violin together, and he gave me chocolate—very romantic for 9-year-olds. Then I caught him peeking into the girl’s change room. I couldn’t avoid seeing him as a creep from that point on. To this day, I am still very disappointed by the incident.
15. Very Cheesy
I worked as a counselor at this summer camp in June for about a month, and one year, there was a very attractive new climbing instructor. He was a hot topic among the other lady counselors. We had a staff orientation before the actual camp started where they held a cookout at this farm, and the climbing instructor happened to be passing out the cheese. And I thought to myself “Oh, this is my chance, I’m going to impress him and be really funny.” So I go up to him with a totally straight face and say “Cheese me!”
There was no reaction, not even a smile, only confusion. And then he finally said, “Cheese please?” So I just nodded in shame and accepted my cheese. He asked for my name, and I gave him my real one, which I shouldn’t have, because he probably remembers me as that girl who asked him to cheese her.
16. Throw Out the Whole Man
I was casually dating a 19-year-old guy when I was 18. He seemed totally normal until I met him at his house before a date, and his mom asked him to take the garbage out before we left. He threw a fit that would embarrass most 3-year-olds which included crying, yelling at his mom, and punching the floor. I pretended that my parents were calling and needed me to come home, blocked his number, and never saw him again.
17. Taking One for the Team
When I was a teenager I decided I was going to impress a girl who was a huge fan of the WWE. I grabbed a metal folding chair and proceeded to hit myself in the face with it multiple times while flopping on my back as if I were Mankind in an actual cage match. At first, she was quite amused, but soon her face turned to sheer terror.
The massive beating I decided to give myself had caused my head to split wide open, which allowed for quite a show all in itself. I went straight to the hospital and received over a dozen stitches all in the name of young love. That was the day I learned that professional wrestlers use a different type of folding chair when “performing” in the ring. The more you know…
18. Common Lack of Interests
Back in college, there was a girl who lived across the hall from me who was drop-dead gorgeous. This was when iTunes library sharing was popular and pretty much everyone in the hall had their music connected to the internet. Everyone on the floor could see your music library and listen to your songs.
I creeped the heck out of this girl’s Facebook and music library, basically putting in every single band and song that she liked in hopes that she would see my playlist, notice that we had the same taste in music, and then, would want to date me and hook up and stuff. It didn’t work, and I’m still embarrassed when I remember it.
19. Call the Fire Brigade
This one girl in high school faked a seizure because I told her that I already had a girlfriend. The gym teacher called 9-1-1 and when the paramedics got there she just got up and ran off. I guess she got in some pretty big trouble for doing that.
We were really hitting it off until he replied to something that I had posted on social media. It was about catcalling and the comments some people left on that post were saddening and frustrating, so I shared it to get support from my friends. One comment was, “Women always get so offended when we catcall them. If we give them compliments, is it that terrible?”
My crush replied by laughing at my post and saying that the people who commented were right. I quickly lost interest in him, and I’m glad that it happened before my crush went any further.
21. Ferry Godmother
I was in New Zealand and was going to a beach party with some girls from the hostel I was staying at. To get to the party, you generally needed to take a $2 ferry across this inlet which was about a kilometer wide. I decided to try and swim it instead, thinking it would impress the ladies. About halfway through my voyage, I realize that I am slowly being swept out to sea and am also quickly losing strength.
I’m not sure how, but eventually I made it over to the other shore, about 100 meters away from the pier. The ferry had docked about two or three minutes before me, and I just nonchalantly walked over to meet the girls as if I hadn’t just swum against a current to near exhaustion and been swept out to sea. When all was said and done with this, there was some good news and bad news. The good news was that this stunt actually worked, and I ended up hooking up with one of the ladies involved. The bad news was that it turned out the $2 fare was for a round trip, so I still had to pay $2 to get back once the party was over!
22. Big Man, Small Ego
We were hanging out at his house when he ‘jokingly’ blocked my way when it was time for me to go and wouldn’t let me pass. I asked him to let me by, when he wouldn’t, I told him I was uncomfortable, and he called me a crazy witch. That was the end of that for me.
23. Head Over Heels
While we were both on the dance floor, I headbutted her intentionally and tried to play it off as if we just happened to bang heads. I thought that the combined experience would bring us closer together. It did not—I was just drunk.
24. A Good Old-Fashioned Game of Phone Tag
There was this woman who I thought I had been getting along with really well. One day, she gives me her number and asks me out for that weekend. Great news, right? I call her later that day and she doesn’t answer the phone or text me back. Then, she sees me a couple of days later and apologizes, explaining that she just doesn’t check her phone very much.
I confirm that we still have plans for the upcoming weekend and she says yes. When the big day finally arrives, I show up all excited to meet her for the date. She is nowhere to be found. I call her phone several times and she doesn’t answer. After a while, I eventually leave and accept the fact that I’ve been stood up.
The next day, I see her again and she apologizes profusely, stating that something had come up at the last minute and that she wasn’t able to get in touch with me in time. I give her the benefit of the doubt and we make plans again for a few days later. I call again before we’re supposed to meet up. However, this time I decide to add a bit of a twist.
I call from my other phone, which was a number she didn’t have or know. Amazingly, now she answers! I say who it is and she hangs up on me. Crush over.
25. Crush and Burn
We were messaging about the homework in our class when he asked for my opinion on a poem he wrote for his crush. I had some hope that it was me and this was going to be a cute way for him to tell me. Nope. It was actually a poem for his crush and he used her name in it. I said it was good even though it kind of hurt inside.
26. Taking Too Long
My crush was going to a party one night, and I said, “You seem pretty unenthusiastic about going.” She replied, “Don’t use big words.” Crush over.
27. Say Hello to My Little Friend
I bought a hedgehog off of someone, planning to give it to my crush to keep as a pet. I was very young and didn’t have much of a thought process past “she’s definitely going to like me after this!” Unfortunately, her parents said no when I showed up at her house to deliver this unexpected gift to her. I ended up having to keep him myself for the next seven years. He turned out to be the sweetest boy ever, though, so I’m pretty happy!
28. This Relationship—Like You—Won’t Hold Water
True story: took a girl to get her septum pierced. While at the piercing parlor. she said she had to go to the bathroom. Went, and came back out and asked me to step outside with her because she had to make a phone call. When we got outside, she proceeded to tell me she had pooped her pants and we needed to leave. I’d driven us to the shop, so had to drive her about 15 miles back to where she had parked her car.
About halfway there, she pooped herself again. I dropped her off. Went home. Slept on it. Decided not to be a jerk about it; accidents happen, everybody poops. So, we hung out again a couple of days later. We stopped at a store and got out of my car and she asked me if her behind was wet. I looked and said yeah it was. “Oh, I just peed,” she said, like it was nothing. I then realized something was seriously wrong and removed myself from that situation.
29. Running Out of Options
I signed up for a half marathon training group so I could spend more time around him—only to then find out that his girlfriend is also in the running group. At least I’m getting into good shape.
30. It’ll Cost Him an Arm and a Leg to Get Over This
I have noticeable scars on my legs from an autoimmune disease, and I had a very big crush on a guy who had recently transferred to my college during the fall semester. We had been spending a lot of time together, until spring came around and everything changed. What happened was that on the first hot day of the year, I wore a pair of shorts and my crush saw the scars on my legs for the very first time.
When he noticed them, he reacted by literally leaping four seats back from me in disgust. All of my feelings for him were instantly gone and I never spoke to him again in my life.
31. Relatively Strange
I moved from California to Tennessee when I was like 11. I always heard the “cousins in the south” jokes but didn’t think much of it. It turns out I had a female cousin my age there and for two years she pursued a relationship with me, which I found super awkward. We actually weren’t really cousins as we moved there to be closer to my stepdad’s family which she was a part of so there’s no blood relation, but still.
Her last-ditch effort when we were both 13 and I was about to move back was, “We don’t have to be boyfriend and girlfriend. We can just kiss and do other stuff.” I told her I still was not interested and, at this point, it’d be really weird because over the last couple years I have just thought of her as family. To which she responds, “God, you’re so weird. It’s not a big deal! I already slept with Jeff and he’s my actual cousin!!” Jeff was indeed her actual cousin.
32. First Is The Worst
We slept together for the first time. After, she told me that she had slept with some other guy I hated just before we met up because she didn’t want to be “inexperienced” for our first time together. I thought losing our virginity together was going to be meaningful. Instead, she completely ruined it. Oh, and after we broke up, she got together with the other guy.
33. Flipping out
I tried to do a backflip to impress my crush. I had never actually done a backflip before, not even on a trampoline. Nevertheless, I decided to just go for it. I wound up just jumping backward and hitting my head really hard on the ground. The next thing I remember was waking up and throwing up a bunch. I was rushed to a hospital, where a doctor called me an idiot and diagnosed me with a minor concussion. He said that I did not have to worry unless more concussion symptoms began to appear, which thankfully they didn’t. As for my crush, let’s just say that if she ever did have a thing for me (which all of my friends say she did), it was definitely gone after that day…
34. Starting to Sweat
Getting up from the bleachers to play dodgeball in gym class, I tried to impress a girl by pulling my sweat pants off while yelling “LET’S DO THIS!” I ended up accidentally yanking off everything, boxers and all…
35. Someone Needs a Decaf
First friend in college, she sat next to me in English class and we immediately clicked. One day she suggests we go out and study together for finals, and I didn’t give it much thought. Turns out she liked me as much as I liked her, so you could imagine my reaction. It was what happened next that changed the mood. Orders a coffee, they make a small mistake and she flips out.
Starts cursing at the cashier, demanding a full refund, and an apology. I sit there confused, this is the same girl who looked shy and reserved when you first meet. She walks out, I apologize profusely and follow after her. She has the nerve to blame them and I tell her it won’t work out. The last week was awkward to say the least, she refused to move seats or sat next to me if I moved and acted like I was to blame for not taking her side. Like, no, you don’t treat people like that.
36. What a Croc!
I swam across a river filled with crocodiles to impress my crush. When we were together later, she admitted that this was the one thing that made her have second thoughts about going out with me. Don’t try impress crushes, just talk to them—even if swimming across a crocodile-filled river seems easier.
37. Around the World in 80 Minutes
There was a woman I went on a date with who I thought I was really starting to like. To give a little bit of context, this girl was a friend of a friend, and she seemed really chill and very put together. She had just recently gone through a divorce, but she seemed to be handling it really well. Initially, she impressed the heck out of me.
So, I ask her out and we make plans to go grab a coffee. When the day arrives, she shows up with her kid, who is about 8 years old. The kid basically just sits there covering his ears through the whole conversation. We start talking and the more we talk, the more I realize that she is super, SUPER insecure about everything and has almost no self-confidence.
Her husband had apparently spoiled the heck out of her. He had provided for her every physical and emotional need and, now that he was gone, she didn’t know what to do other than look for another guy who might be willing to take care of her in the same way he did. The topper was when she told me about how she was hoping to find an “old-fashioned” man—as in the kind who would pull her chairs out for her, take her out to really high-end restaurants, pay for the whole bill wherever she went, and whisk her off to foreign cities on a regular basis to stay in fancy, uber-expensive hotels.
I’d say right about that point was when my initial feeling towards her disappeared pretty abruptly. I was definitely not down to be used by someone like that, to fill some void in her life and spoil her like crazy when we had only just met. Honestly, I was pretty mad about all this in the moment, but now I look back and I just feel bad for her.
She put up with all kinds of garbage from her husband—years of lies and cheating on her—and he still ended up leaving her in the end. But I guess that’s what happens when you outsource your sense of self to someone else.
38. Startled Tinkling
I really needed to go to the bathroom in the fifth grade. The lunch lady wouldn’t let me go. When she finally did, it was too late. I ran out of the cafeteria and into the hallway to randomly meet my crush face to face. It was over then. I just wet my pants. I’m still friends with her to this day, though!
39. Momma’s Boy
I was an exchange student in Germany for a semester during high school. My host mother developed a crush on me. She and I would often be the last to go to bed, and she would stand in the doorway to my room and say things like, “You know I love you much more than just being your host mother,” and insinuate that her husband wasn’t making her happy.
Or she would sit on the edge of my bed sometimes touching my legs until it was too awkward and she would leave. She made very sure to let me see her whole naked body in the sauna. But her advances were only a minor annoyance for me. This awkwardness was compounded in the last month or so when I had developed a heated, lustful relationship with her daughter who was my age.
40. Momma’s Boy
I met this person, drove from the Midwest to Dallas with him, and was stuck there for two days before my train ride home. We were both 22. He was mean to his mom and demanded money from her in front of me so we could go out. Then he called his grandma and pressured her to get even more money for our date. I was right there the entire time. It was very uncomfortable.
41. I’ll Pass on Trying This One At Home
I was about 12 years old and riding my bike home from middle school when I saw a pack of pretty girls ahead of me, about five years my senior. On the other side of the street was a boy who I had a big crush on at the time. This stretch of road meant that I had to ride on the pavement, so I thought that I could be cool and impress the boy by aggressively overtaking these older girls.
My plan was to drop down into the road, gain some ground, and then jump back up the curb once I passed them. Well, I almost lost my life that day. My determination to impress the boy overtook the part of my brain that deals with logic, and I severely miscalculated the jump. I skidded against the curb and it bucked me out to the middle of the road into oncoming traffic.
I scrambled to get back onto the pavement and my bike flew clean off the ground. I was then propelled head first into a bush.
On the bright side, goal achieved: I overtook the girls, and my crush did come over to help. He even called me cute when I started crying, so I took it as a win. I haven’t been on a bike since, though.
42. The More You Nose
In elementary school, I liked this girl. When I saw her touching her nose one time, I saw my opportunity and shouted out “EW, YOU’RE PICKING YOUR NOSE!” for everyone to hear. My rationale was that by embarrassing her, she would think that I was cooler than she was—and would therefore be interested. In hindsight, I was just being an irrational meanie.
43. Not One to Let Them Down Easy
I asked her out over Facebook. Cowardly? Maybe, but in my defense, hadn’t ever really asked anyone out before and just…couldn’t every time I tried to do it in person. She was also my first crush following the breakdown of a long-term relationship. She said no, that she wasn’t interested in a relationship at that point. Ok, cool. Understandable.
That’s her right and I wasn’t happy about it, but I respected her right to turn me down. Less cool was when she told basically everyone that she knew about it in kind of a snarky condescending way. A friend of mine told me when I got back, and I just wanted to disappear. Folks, you’ve got the right to tell someone no. If someone asks you out, it doesn’t matter who, you are under no obligation to say yes.
But please, if you turn them down, respect their dignity enough to keep it between the two of you. Unless they’re being creepy. Then all bets are off.
Knew a guy who went to a bowling party with a girl he had his eye on. He realized he could stick his thumb in a bowling ball and hold it using just his thumb. Thinking this would impress the girl, he held it over her head and said “Look!” The girl looks up, the ball falls, it breaks the girl’s nose, blood everywhere.
45. So You Think You Can Dance
This is really horrible and stupid, but I’ll tell the story: I used to be pretty good at Dance Dance Revolution. I owned my own Cobalt Flux (still do, in fact) and knew all of the nine-foot songs cold, and could pass Max 300. Our freshman year of college, they had a game night very early on—I guess it was to get the freshmen to mingle a little bit. Well, just my luck, among the arcade games, they brought in a DDR machine. I was totally shocked to see it when I walked into the student union.
This ridiculously hot girl from one of my classes was dancing on it. Obviously, she was doing a horrible job, like most people do who don’t play the game, but she was laughing and being adorable. Now, instead of being the smart kid and going back to my room to get sneakers, I decide it’s a good idea to just play in my flip flops. After getting off to a great start on Afronova, I decide to get fancy and start doing spins while on the pad.
I then promptly fell off of it. Everyone in the student union was watching. I was known as “that DDR guy” for the first two months of school.
46. A Year to Build Up, One Sentence to Dismantle
For over a year, I was heavily flirting on and off with this dude I had met at a party. We were both really attracted to each other and went on several dates, all of which were great. I really think we had a genuinely deep connection with one another. Nevertheless, we were just casually dating here and there, rather than seeing each other more seriously on a regular basis.
After our last date, I went back to his place and we started heavily making out on his bed. We were ready to start doing the deed when I asked him if he had a condom, to which he replied, “Nah, we won’t be needing one tonight! I had an STI a few weeks ago and I just finished getting it all handled!” What proceeded was the fastest 180 I ever did in my life. I got the heck out of there as fast as I possibly could and never looked back. Sorry, but I don’t mess around with diseases, bud.
47. Manic Pixie Nightmare Girl
She was a cute intern at the company I worked at who I had a small crush on in the first week or so, but she came on so strongly that it was like a semaphore dictionary of red flags. When I realized she was a little intense I started talking to her a little less at work, though I was still perfectly friendly. Some lunch breaks, she would put on earphones and salsa dance seductively by herself in the little break area near my desk.
She was a good dancer, but dude, c’mon. Things kinda culminated when she turned up on my doorstep at 9pm on a really rainy night. I was like what are you doing here, but invited her to come in to get out of the rain. She refused several times, preferring to stand in the pouring rain while she apologized for everything she’d ever done (no specifics) and then went on a rant about how stupid I was for not coming to her salsa dancing classes when she’d invited me.
I was mostly too surprised to respond, but she was doing enough talking for both of us. Then after 10-15 minutes of this, she said “I should get home,” turned around, got on her bike, and rode off. Didn’t even say goodnight. One of my housemates had awkwardly been standing in the kitchen for the entire thing and had heard her whole spiel, and she was like, “Dude, that girl is about six different flavors of crazy, you were so nice to her.”
It only occurred to me after she left and I was talking about her to my housemate, that I’d never given her my address. To this day I have no idea how the heck she found out where I lived, short of stalking me and following me home. She wouldn’t have had access to any HR docs at work, she was just an intern. I actively avoided her at work after that, though she acted like nothing had happened.
When the end of her internship came up and she went back to Germany, she bought me a present. It was an A3 blown up photo of her laying on her front sunbathing without a top, which had been her profile picture on her work Skype account until she’d been asked to change it because her manager said it was inappropriate. It came with a really long letter that basically was telling me what an idiot I am for about five pages.
I’m just glad the crush only lasted a week or so and at no point did I start thinking with my member.
48. A Bridge Over Troubled Water
I was riding across a bridge and saw this hot guy taking his shirt off on the other side, so I decided to ride by to get a closer look and say hi. As I turned my bike from the bridge and onto the path, I turned too far and fell a couple of stories into the water. I entered the water through a four-foot gap between two boats. I don’t know where the guy went, but he certainly didn’t save me.
49. On the Lamb
When my younger brother was about nine years old, he had a “girlfriend” who lived in our development. Our development was right next to a farm and there were sheep. One day, his girlfriend said she wanted a sheep, so he climbed the fence, made a leash out of rope and attempted to take the sheep out of the fencing. There was a ram in the area and it started to chase him away. He managed to get away unscratched, but twisted his ankle and got yelled at by the owners. I had to take him to the owners to apologize and they said they were just worried he would get hurt and offered to take him into their farm to see all the animals.
50. From First to Worst
The girl I liked asked me out in front of a bunch of her friends who all knew that I was mega into her. They seemed to enjoy seeing my excitement as I responded, “Heck yeah! Are you serious?” Some of the friends then started to giggle. I was suddenly so nervous that my head felt like it was about to pop off and blast up like a rocket. Then she said “HECK NO! HAHAHAHA!!”
Just like that, I was crushed and I instantly started to despise this girl with a passion. All of her friends soon joined in on the fun, letting out a joint “HAHAHA!!” in unison with hers. I got over this incident eventually. Well, kind of…
51. Mark of Detention
My most awkward moment with my crush was when she asked to borrow my ruler for a project since there were no extras beside my extra ruler. Then she asked why there was a mark at five inches on it, so I had to explain to her what I’d done with it. Then we both got detention.
52. Means to an End
I finally asked a girl out and she eagerly accepted. About halfway through the date, she turns to me and says, “You know what? I’ve decided to stay with my fiancé.”
53. Barking Mad
In third grade, I had a huge crush on a boy in my class. My dog had to be put down, and I came into class the next day so inconsolable that my teacher sent me to the nurse. When I came back to class, the kid’s reply nearly made me burst into tears. The little jerk looked me right in the eyes and said, “It’s just a dog. Who cares?”
54. Every Idiot Dance Now
I was abroad in the Dominican Republic. They had a dance competition on stage that anyone could enter, and it had around 200 people watching. I was about nine or ten years old at the time and I spotted a cute girl who must have been around 14 or 15. Obviously, I decided that the best way to get her attention was to get up on stage and dance my heart out. Queue three minutes of awkward public shuffling while maintaining constant eye contact with that girl, as well as horrified and queasy looks from my parents.
The coordinator cut me off early by pretending that the speaker had stopped working. I got a nice pity clap from the audience.
55. Sounds Like a Winner in My Book
Back in middle school, I wrote out the lyrics to “Loser” by Beck on a note to a popular girl in school. However, I changed the lyrics from “I’m a loser baby, so why don’t you kill me” to “I’m a loser baby, so why don’t you kiss me.” I totally thought it was a smooth move at the time, and I even told her that I wrote the whole song myself. I eventually got the kiss though, so can’t complain.
56. What Kills a Mood Like a BBQ?
Cute girl in ninth grade, there was a party over at her house, out in the country. Had a big ole crush on her. So, she says they raised chinchillas, and then everyone wants to see the fuzzy critters. There were about a hundred of them, the ammonia smell was unreal. There’s a platform with battery cables on it, and I asked what that was for, she said, “Here I’ll show you, have some ready to go anyway.”
She grabbed a little fuzzy critter, clamped the cables on it, and threw the switch. Without missing a beat took the life from that critter. It was bizarre that a teenage girl could electrocute and animal that easily. No more crush, I was actually afraid of her a little after that. It kind of sucked the life out of the party to say the least.
57. Uninvited Pest
My first “girlfriend” lasted one month of grade six. It was a love story for the ages. It all started when she passed me a note stating her feelings for me. Lucky me, I thought! Without ever having spoken to this girl, you have won her heart—you magnificent devil you! And with that, I proclaimed her my girlfriend in my mind! In retrospect, she probably didn’t know we were now in a heated relationship.
We attended the school dance together within the same week of our newly kindled love. We had at least one dance together—things were getting heated. I followed that up the next week by doing what I believed one had to do to get the girl of his heart’s contact information—I perused the Yellow Pages and found her phone number and dwelling establishment. One day, I started walking to her place. I didn’t warn her, but when does love ever need to be alerted?
I found her house and introduced myself to her father in the driveway as his daughter’s new boyfriend. I then creepily, in that romantic kind of way, knocked on her door. She opened it and with her loving voice she said “What are you doing here? How did you know where I live?” This was a very good question—I was ready for “Hi” or “It’s nice to see you,” but not this. I mumbled some charming words of confusion to her in my ever so enchanting tone, and briskly backed up and out of the awkwardness. I decided to play it cool and not talk to her for two weeks.
Once this was up I decided I would invoke passion back into our relationship by spreading the good word of how our love had spread. I took home with me one of the English textbooks we read daily from the classroom’s bookshelf. I spent the whole night cleverly writing wherever there was space in the book how much passion the two of us had for each other. There were hearts and initials all over the place.
The next day I returned the book to its spot before class began. I was pumped everyone was going to be jealous of my love life. No one was jealous. There was much laughter to be had, and the class (and my girlfriend) were now for the first time informed that we had been dating. She seemed to be taking it badly. It was at this point I decided I can’t be with a girl who is shocked to find out we are dating.
I did make sure to take the book out one more time—and burn it. I hope to one day collect up the courage to actually tell her we are broken up, I worry she won’t take it well.
58. Scarred for Life
I fell hard for a guy in high school but he lived far away from me. Talking with him, I found out he has a scar that he was shy about and ashamed of—he would never take off his shirt for pretty much his whole life because of it. So one day, I used a black marker and highlighted all of the scars on my body and took some pictures and wrote him a letter that said, “We all have scars—it doesn’t make you any less handsome.”
When I was nine or ten I had a crush on my babysitter. I stayed up later (after reasoning with him on bedtime) and tried to act all cool and teenager-y, which included things like sunglasses, lounging around apathetically, and generally acting independent (saying that I could go places on my own, had many ex-boyfriends, etc).
59. I Wanna Rock and Roll All Morning
I have an amazing story about something like this! I was 14 years old and totally fully in love with this girl from my class. It’s important to mention that we often kinda flirted for a whole year, but got nowhere. She was the kind of girl who likes attention, so you can imagine how she kept me all worked up despite knowing I actually had no chance with her.
Since it was getting close to Valentine’s Day, I decided that I was going to try to impress her and win her over by learning how to play guitar and surprising her with a serenade of all of her favorite songs! After spending a full week practicing like a madman, I somehow managed to actually learn to play two of the songs that I knew she loved.
So fully prepared and convinced that I had hit the jackpot, I show up at her house on the morning of the 14th and call her out, telling her that I had a surprise for her. She pops her head out of the door, takes a quick glance up and down at me and my guitar and nopes the heck out of there, asking me politely to please leave. Well, my master plan might not have worked out as I had hoped, but hey! At least I now know how to play the guitar!
60. Saving the Best for Last
Back in college, I had a really big crush on this guy from my class who was very into magic. After thinking about it for a while, I decided that the perfect way to get on his good side would be to surprise him and attend one of his magic shows. So, that very evening, I went to see him perform at a college event. I was pretty impressed with his skills—that is, until he got to the grand finale.
His last trick involved him taking his pants off on stage and literally pulling a card out of his behind. There were toilet paper remnants visible. I disappeared from that theater real fast!
61. Presuming Pastor
My early high school crush was the daughter of a pastor and my friends pressured me to ask her out, which I did via email. I was too dumb to realize the email she gave me was her dad’s email. It was the 90s with AOL and the email was straight up her father’s name @aol. Anyway, it took me like ten years to realize the verbose smackdown I received in reply calling me presumptuous probably came from the dad, but I remember I had to go to dictionary.com and my 15-year-old self was puzzled over the meaning of presumptuous for like a month.
62. Little Black Book
I was in high school sitting in art class when this guy walks over. I didn’t particularly like him or not like him. I didn’t know him that well. He stops at my table and casually asks for my phone number. I say, “Sure!” and he pulls out a piece of notebook paper. When I saw what was written on that paper, my stomach dropped. It was filled with phone numbers all suspiciously the numbers of nearly every girl in our grade.
It was too late to say no and I got a phone call from him at least a dozen times a week for a month. The fact that no one ever picked up after the first time, which boy, was that an awkward phone conversation, never stopped him. I just pictured him calling down that list every day.
63. Busy Day
I had known this guy for a few weeks and finally set up a date. I texted him a couple days before to say hi and asked him how his day was. His reply made my jaw hit the floor. He told me it was great because he’d slept with someone that morning, then he had a good day at work, and then had a date with another round of banging with a totally different person.
On the one hand, thanks for making it easy for me to dump you, and on the other hand, maybe work on not being a complete jerk.
64. Tae Kwon No
When I was a teen, I took Tae Kwon Do classes and there were these two beautiful girls around my age in the class with me. They always liked to go and have a smoke behind the mall before class. I wanted to be cool and impress them, so I decided to take it up myself. It was about two weeks in when one girl came to class early, so I went out and had a smoke with her.
Then, the next girl came in and wanted to have a smoke, so I went out and had another one with her. When we came back, we started doing our warm-up laps and I suddenly felt very queasy. I realized that I had to throw up, so I ran outside. I threw up all over the glass wall of the nearby Dairy Queen, with all of the cashiers and terrified patrons inside looking on in horror.
65. Putting the Independence in Independence Day
One year, I went out on a 4th of July date. After going out to dinner, I took her out on the lake in a canoe to watch the fireworks. It was awesome. Unfortunately, young macho me felt like he had to impress her by turning down an offer for help with lifting the large canoe, so I manhandled that thing like it was nothing. I put her in it while it was still on the grass and continued manhandling it to show off just how strong I was. The next morning, I had to call in sick to work because my back muscles were so strained I physically could not get out of bed. My back was sore for over a week!
66. With This Ring, I Thee Dread
I’ve told this story before, but when I was about 8 years old, we took a field trip to the Field Museum here in Chicago. During our lunch break, I decided to wander off to the gift shop and see what they had. I had a huge crush on this girl named Victoria in my class and I saw this ladybug ring for a couple of dollars. I knew she liked ladybugs and I had money my parents gave me to buy something at the shop, so I decided to buy the ring and give it to her.
I was really nervous and kept waiting for the right time to do it. I eventually decided to just go for it and walked up to her near the end of the trip. She was with some of her friends which made me more nervous, but I found the courage to do it. She looked at the ring and laughed. Her friends joined her, and she then tossed the ring in the trash.
I was completely devastated and tried hard to hold back my tears. Even though I’m over it now, that completely screwed my confidence with girls for a long time. Looking back, I may have embarrassed her too giving it to her in front of her friends, which is why she reacted that way, but whatever the case, it’s probably the most embarrassed I have been in my life and it definitely made me lose interest in her.
67. Taking the Plunge
Freshman year of college, we got placed in “inbound” orientation groups to do team-building adventure activities, ostensibly so we would have some friends on the first day of school. Most of the activities were normal—things like bike trips, some hiking, kayaking, etc. On the last day, we kayaked out to this island on the lake to go cliff-jumping. Now, I’m terrified of water, but there was this super hot guy in my group, Kevin, who had taken a liking to me.
I was only going off the 10-foot cliff, while Kevin and the other two boys went off the 40-footer. Kevin challenged me to be the only girl in the group to do the 40-foot cliff, and…I did it. And landed wrong. And broke my tailbone hitting the water. And had to kayak home.
68. Bloody Mary
When I was like ten or twelve, I hid behind a building and punched myself in the face multiple times so that this girl I liked would see that I can bleed without crying.
69. You Make Me Feel So Young
In my case, I was the victim of the instant change of heart, unfortunately. Back in the good old days of kindergarten, I used to often get chased around the class and kissed when caught by this one girl who I used to play with all the time. She had admitted at one point to having had a crush on me—whatever that means when you’re in kindergarten—and innocent little me thought that it was a pretty cool and interesting development.
Then one day, I had a little accident. My face got crushed into the asphalt and I ended up with scabs all over my forehead. When the girl in question saw me in this condition at school the next day, she reacted by pointing at my face as she shouted out: “Eeewww, what’s that on your face? I don’t have a crush on you anymore!” She was crazy. Girls were icky. I have never been happier to have a bloody face.
70. I Spy with My Loving Eye
This girl who I’ve never talked to used to send me messages on Facebook all the time saying that she saw me driving around town. It got to a point where she sent me messages saying she saw me parked at my friend’s house and that we should hang out. I’ve never talked to her and I never replied to the messages. I think she finally got the point because she stopped.
It really creeped me out though. I don’t know how she figured out who I was or what kind of car I drive.
71. Misaligned Stars
I was saying bye to my crush and went for a hug but she went for a handshake. Then I started to go for a shake and she went for hug. It lasted a while. My dad was watching from the car. He was so embarrassed for me.
72. Not So Dinosaur About This
I’m a paleontologist, and she’d stopped me at dinner while discussing careers to ask, “Hey. So, this might be a dumb question but…” In teacher mode, I said, “No, of course not. There are no dumb questions.” She went on, “So, did Jurassic Park happen?” I assumed this was the age-old “Is Jurassic Park possible” question. I was so, so wrong.
I said, “Good question. No, we can’t clone dinosaurs. DNA degrades over time…” She interrupted me, “No, I meant, did Jurassic Park happen, like did it actually happen, though?” Pausing, I asked, “What do you mean? Like did dinosaurs take over a Costa Rican island in the 90s?” She, an elementary school teacher, nodded.
73. You Can Be Everything You Want to Be
When I was in sixth grade, I had my very first hormone-fueled mega crush on this guy in my class. We had one of those “star student” things going on in our class where each week a different student was showcased on the bulletin board with pictures and facts about them for all to admire. The idea was that by having this, we could all get to know each other a little better.
One of the things we had to include on the form we filled out when it was our turn was what we wanted to be when we grew up. No joke, I tried to impress him by putting more than ten different things crammed in there. Among them were actress, musician, teacher, doctor, and plenty more—just to make him think I was that cool. Needless to say, my plan didn’t work at all.
74. Sounds Like True Amor
In high school, a few hours after school was let out one day, I was talking to this guy I had a crush on when he mentioned that he had left his Spanish notebook in his locker and had a test the next day. He lived far away and I lived close, so I offered to help him out. I walked a mile to the school, went to his locker, called him, got the combination, and read 10+ pages from the notebook to him while I sat on the hallway floor and he took notes.
75. High Standards from a Low Place
I decided to confess my feelings to him. And I thought that the worst that could happen was him just saying something along the lines of ” I’m sorry I don’t feel the same, but I’d still like to be friends.” His exact words were, “Why would I like someone as ugly and fat as you?” His best friend at the time overheard us since he was nearby and laughed about it with him in front of my face while I just stood there shocked for a few seconds.
76. That Went Well…
I was in the gym on the treadmill a while ago, and the only other person in there was this hot chick doing yoga or something on the floor mats. For some reason, I got it into my head that I could impress her by doing a cool move to get off the treadmill when I was finished. Like, plant my feet on the treadmill belt and just kind of slide off the back.
However, I didn’t slow it down enough first, so when I planted my feet, my legs shot out from under me, I body slammed myself onto the treadmill belt, and was ejected gracelessly off the back. I picked myself up as quickly as I could, but there was really no way to play that off like I had intended it. She didn’t say anything, but her derision was palpable from across the room. I left quietly…
77. Don’t Have a Stroke
This girl I liked was pointing at something while we were sitting in a dark theater. For some reason, I decided it was a good idea to start stroking her finger. Didn’t end well.
78. Deafening Discomfort
I had this crush on a girl in ninth grade and I finally had the courage to tell her. She didn’t say anything the entire time and by the time I was finished we were just awkwardly staring at each other. So, we sat there in a miserable silence, until I muttered, “I’m so sorry,” and watched as she nodded and just walked away with this stony look on her face.
She avoided talking to me after that. Even though it’s been eleven years I still cringe whenever I think about it.
79. Telling Tall Tales
My brother had a girl he didn’t like after him through high school. I was 11 and would always answer the phone. I made up increasingly ridiculous excuses and tales of where he was, partying, doing drugs, heading to a major drug deal, on vacation in Japan, training to be an assassin, it was fun at first but it got annoying pretty fast.
He still doesn’t know how she got our number.
80. Keep It Down
I crushed on a girl for a couple of years and didn’t ask her out because life was busy for me, but eventually, I was able to ask her out. I took her to the movies to see the most recent Star Wars movie. Before the movie had even started, she was slamming drinks down, with which I have no issue, but she was dang sloppy.
She talked throughout the entire movie and constantly looked at her phone. Funnily enough, she also made some mean comments towards other people for “disrupting her viewing experience.” She genuinely didn’t think she was being hypocritical. It was so cringey. Later that night, we drove to a gas station so she could get a pack, and she was being really rude to the cashier.
It wasn’t his fault that he couldn’t understand what she was asking for in her belligerent state. She tried to convince me to stay the night with her, but any attraction I had for her was completely gone.
81. She Brings Out the Animal In Him
I hoarded a bunch of stuffed animals I won at a local arcade over the summer for this girl I really liked, thinking it would win her over and make her want to be mine. One night, I thought “you know, tonight’s the night. I’m going to surprise my crush with all these stuffed animals, and she’s going to fall in love with me on the spot!”
So, I threw them all into a huge white garbage bag, walked two miles down the road to her house as the sun was setting, and knocked proudly on her door. As she began answering the door, I cleverly concealed my bag of goodies behind my back. She awkwardly asked me what I was doing at her house and I revealed the big surprise.
She slowly grabbed the bag from me, looked inside of it, and gave me a very awkward thank you as she slowly began closing the door. Right then and there, I realized that I had miscalculated the gesture and that I probably looked like a huge creepy nutjob. I power-walked back home and, to this day, I still think about this incident from time to time.
I think it’s my brain’s way of punishing me eternally for putting it through that whole thing. I’m loaded with stupid stories like this one because I am a huge romantic and, as such, I often tend to get bitten in the behind in one way or another because I just don’t seem to see things clearly when I’m in the haze of being in love.
82. This Just In: Your Plan Didn’t Work!
I lied to a guy because I didn’t think we’d have anything except a brief encounter. I told him that I had experience in journalism when, in reality, I had actually only taken one class on the subject in college. On our first date, he took me along to report on a local clash between law enforcement and citizens. I got tear gassed and robbed. He was not impressed.
83. Happy Ending?
Okay, so in high school, I had a crush on this girl for like two years. We both wound up in the school musical together and I was cripplingly awkward in person. Now, the director would email all of us the same letters, weekly, so I found her email address and I was gonna send her an email, but I realized that would have looked creepy. So instead I did something 20x creepier! I created a fake email account of a bisexual girl, and sent her emails that implied she had a thing for both of us.
THEN, I started talking to her in person, and asked her if she’s been getting any strange messages. She said yeah, and we started talking about it, and out of her pure unadulterated fear of this psycho stalker, she latched onto me like a… friend. Just friends. That didn’t go at all according to plan, but could’ve been worse. Then, I realized I had to make a wildcard move if I wanted anything to happen.
So, I told her EVERYTHING. And somehow, she wasn’t the least bit weirded out. We’ve been best friends for four years now, and dating for almost half of it.
84. Just Warming Up…
In high school, I was deeply in love with a girl who knew me only as the creepy guy who stared at her in choir practice. I think my most pathetic attempt to garner her affection is a toss-up between that time I made a song on a digital music program for her and gave her a CD of it, or the time we were in one of the school musicals together and I sent her a plastic rose (they were selling them to support the show) with a note on it signed “Love, [my name].” I cringe every time I think about high school…
85. A Swing and a Mistake
When I was a freshman in college, there was a crazy hot girl I would have happened to not mind going out with. She was also my little sister’s dance teacher. Anyway, we’re walking to class and thinking I would be a chivalrous gentleman. I reached to open the door for her. Except instead of grabbing the handle, I completely missed and only grabbed air.
I managed to catch myself before I got the ground but that was the last time we walked to class together.
86. Be Objective
My middle school crush was on the big-chested side of the spectrum and one time when she was nervous because of finals, I accidentally said, “Do your breast.” For the rest of the day, we couldn’t look at each other.
87. Morning Coffee
In high school, I was always the nice kid. This always brought me trouble with a few people because I was simply too nice to say anything to anyone. This particular creepy/awkward crush happened when I was about 16. I hung out with a few kids before classes. There was this one girl who I’ll call “R” who hung around one of my friends.
She was one of those strange people who just gave off a really weird vibe in general. On top of the weird vibe, she liked to hang onto the shoulders of her friends and was just too touchy-feely for my liking. On occasion, she’d give me a hug that would last just a little too long. Now, I never thought much of the weird hugs and the occasional creepy stare.
Like I said before, she was an odd kid to begin with and I just chalked it up to her overly eccentric personality. So, I never thought that she might have some sort of crush on me. I was about to learn that I was very, very wrong. One morning, I decide to have a cup of coffee before I went to school, so that made me a little chattier than usual. Well, as I’m chatting with my friends, R and her boyfriend come walking up.
R decides to interrupt my conversation and loudly say, “Oh my God! Your breath smells like coffee! If you were bi and my boyfriend weren’t standing here, I would totally kiss you!” Everyone goes silent and gives this girl the biggest confused look. As we are all standing in awkward silence, trying to figure out what to say, another friend of mine walks into the school.
In an effort to pretend that I didn’t hear what R said, even though I’m sure the dead heard her, I loudly called my other friend’s name and ran to greet her. From then on, I tried to keep my distance from R. I didn’t know how to deal with someone that had a creepy crush on me. Sometimes she would catch me off guard and talk to me.
The conversations were fairly normal but I would always get a creepy “I’m staring into your soul” look complete with a slightly-opened-mouth smile. I was very relieved when her and her family moved the next year.
88. Related To The Matter
My crush immediately ended when I found out that the girl I was obsessed with was…my cousin. We were in a college class together and had been lightly flirting for a couple of weeks. It was a complete coincidence and neither of us had any idea that we were related until a family member casually mentioned to me, “Doesn’t (her name) go to your school?” It was awkward.
89. Swing and a Miss
I was taking my friend to the driving range one day when she asked if her insanely hot friend could come as well. She mentioned that her friend had never hit a golf ball before in her life, so I’m thinking I just hit the jackpot. I’ve got an easy excuse to start talking to this girl, and an excuse to ask her back out one-on-one if all goes well.
So we get to the range. I hit a couple of warm-up shots while she’s getting her clubs rented. Once she gets that sorted out, she comes over and takes the spot right next to me. I decide that this is my chance to impress her by really crushing a ball, so I give my next swing everything I’ve got. Huge mistake. I missed the ball and clipped the ground, causing the club to break right off the pole.
It then proceeded to bounce back and smack me directly in the face, giving me a nice solid shiner—all while she’s still watching. I definitely put on a show for her, but not quite the one I had in mind…
90. You and the Amazing Technicolor Nightmare Coat
I made sure that I was the one to return her jacket when she forgot it at school. When I gave it back to her the next morning, she blamed me for stealing it. We did not end up together.
91. Think Fast!
There was a girl I liked in summer school back in the day. I talked to her older brother and borrowed the game Keymaker from him—and got his number just in case something happened. Later on, I called their house. When she picked up instead of him, I panicked and said “I LIKE YOU” and hung up.
92. Tragic Poet
Back in high school, AOL Instant Messenger was a thing. Every morning before school, I would try to post in my “auto message” some profound statement about love or relationships often using song lyrics. I did this specifically in the hopes that my crush (who was one of my friends on IM) would see it and have some revelation about how awesome I was. Looking back, that was a lot of energy spent for something I could’ve done by just being myself around her.
93. Open Wide
I was flirting with a guy for like two years, it was obvious we liked each other but something always came up and we never admitted it plus he was a little hesitant at times. He finally tells me he really, really likes me. I say I like him too and we make plans to see each other. Without saying hello, the first thing he does is to go in for a kiss.
As he’s getting closer, I can’t believe what I’m seeing. He opened his mouth like he was swallowing something huge. He basically opened his mouth so much that he didn’t even touch my lips but went around and swallowed 1/3 of my face. He stayed in that position for a few seconds without moving his mouth at all and then backed away saying, “Ugh it’s obvious you’re not experienced.”
It was the most awkward thing in my life. We didn’t speak for some time after that and he told people that I’m a bad kisser. We’re 25.
94. Flipped Off
I was spotting her in an informal gymnastics class. I was wearing jeans and had a really big boner that I just hid by tucking up. She was showing off and I was at the end of the pad watching her flip my direction; stupid me was too distracted to move out of the way; she ended up hitting me, tipping me over and landing her face on my crotch. Ouch.
95. So Confused
I took the advice of a good friend of mine for this one. There was a pretty girl who usually had lunch at my dorm’s cafeteria around the same time I did. So one day, before I went to lunch, I stashed a pineapple in my backpack. I ate my lunch as usual. She came in as usual. When I was done eating, I took the pineapple out, walked up to her table, and asked her, “Do you need a pineapple?”
When she started to produce a confused rendition of the word “No,” I cut her off and said, “Everyone needs a pineapple.” I planted the pineapple on the table in front of her and confidently walked away. We never spoke again.
96. From 0 to 100
During my time in a university share house, I lived with a 19-year-old guy when I was 29. After knowing me for a mere five days, he asked if he could paint me naked and even though I said no, he proceeded to tell me he was in love with me. I immediately went to get moved to new accommodation because things got creepy fast.
While I was gone, he left a suicide note on my door. He disappeared for 24 hours. I was interviewed by local law enforcement.
97. Date One Get One Free
In my early twenties my girlfriend’s sister, who was a very well developed 16-year-old, crushed on me hard. She even got my number out of girlfriend’s phone to text me at all hours. It was awkward, the girlfriend didn’t listen and said she was just being playful. The girlfriend shared everything with the sister. Like, way too much.
I ended it all when I received a text in the middle of the night from her sister as I was lying next to the girlfriend shortly after sleeping with her. Her sister was sleeping over at the girlfriend’s apartment and in the living room that read, “I want you to make me finish the way you make my sister finish.” Yikes.
98. Just a Lick
We played Truth or Dare in a large group. There were three guys and one girl. All of us guys had a crush on her. At the time I had a goatee and she was dared to lick it. She used her tongue to draw a wet circle all the way around my mouth. She had really bad breath and I could smell her saliva all day. It was a miserable experience.
99. You Definitely Read This Situation Wrong
When I was 15 years old, I dropped a heavy book on my head to try and impress my crush. It was this old dictionary: a single volume that was easily eight inches thick and probably weighed at least 15 pounds. I laid down on the floor, held it over my head with my arms fully extended, and dropped from a foot and a half in the air right onto my forehead.
I guess I thought it would show how tough I was? Turns out I was not very tough. It sort of worked, though, because I ended up dating her until freshman year of college—but, in all fairness, that was likely in spite of my actions rather than because of them.
1900. The Most Wonderful Time of the Year
I did something very, very stupid. Like SO stupid. I had a crush on this girl, so I decided to leave a box of chocolates on her front porch and just run away. Oh, and all I wrote on the card was “Merry Christmas!”; I didn’t even bother to sign my name. Now, 13-year-old me was very immature in general and totally unaware of how pretty much anything worked, but even by those standards, this was pretty bad!
101. All You Can Eat
She worked at a burger place. I was absolutely infatuated with her, and I would have done anything to see her—let alone to impress her. The place she worked at offered a promotional challenge to eat about four to six huge hamburger patties within a very short period of time. It was like a race, and whoever ate it all the fastest moved on to the next stage. Eventually, the winner would get a bunch of money as a prize.
I went down there to impress her. I ordered the challenge, and she sat with me to record my time. Mind you, I was a pretty large guy at the time and was around 60 pounds overweight. They brought the burger out and I didn’t even give it time to cool. My fat self sat there alone in front of the girl of my dreams at her place of employment and wolfed down a burger way too big for any normal person to eat, all the while slightly whimpering as it badly burned the roof of my mouth. Can you say alpha? I couldn’t, because I burned my mouth!
The aftermath hurt for like three days too, and I was out like $15. If you’re reading this, former crush, you know who you are. Sorry I was a weirdo. I mean, I still kinda am, but at least I’m more self-aware now.
102. By da Vinci Himself
There was This Guy on campus. He was actually a model and also sort of a jerk, but he was so hot nobody cared. The ONE day of my entire college life I decided, “Whatever, I’m wearing my pajamas to dinner I’m too lazy to change,” he comes up and asks if he can sit in the chair next to me. I said yes and then proceeded to cough my entire lungs out while wearing blue leopard print pajama pants.
He didn’t even say anything. He just gave me that look that says, “Uh this person is weird and gross.” It turned out he lived two doors down from one of my friends and we saw him all the time. But at least my story wasn’t as bad as this one: I was not the only person who had a massive crush on him as another friend drunkenly tried to hit on him by telling him, tearfully, that “You’re the man da Vinci based the Vitruvian Man on,” but this boy was too stupid to realize what a compliment that was.
We all called him Vitruvian Man the rest of the time he went there.
103. Not in This House
A girl in my sister’s year always followed me about school. They were 12 in Year 7 and I was 16 in Year 11. She was this little Ginny Weasley type whose upper lip was raw from constantly licking her dry lips. Even my friends had noticed she was following me around. It didn’t bother me that much until one day I got home and she was there with my sister.
Later that day I told my mum about it, she told my sister, and she was never invited over again.
104. Sweetheart Palpitations
When I was 14, I’d been hospitalized and he came to visit me—the second he walked in, one of my monitors started beeping loudly cause my heart rate had spiked. He noticed. My mom noticed. His dad noticed.
105. No Pain, No Gain
A girl on a date pinched me and then commented with amazement that I seemed to have an impressively high pain tolerance. Running with it, I told her that I was basically impervious to pain. On our way out of the restaurant, I noticed a patch of cacti next to the parking lot and told her that I could walk straight through it and be completely fine.
I got about four feet into it and was in so much pain that I couldn’t move anymore. Thankfully, she said “please come out of there! I already like you!” HAHAHAHAHA! I got out of the patch safe and sound minus one shirt, plus one bloody nipple. We went out two more times.
106. On the Road Alone
Way back when, my first ever serious girlfriend was home alone one day and invited me over to spend some time with her. It didn’t take long for the idea to plant itself in my head that this would be the day I’d finally get past first base. I’m all of 13, hormone-addled, and obviously confident beyond a doubt that this girl is the love of my life.
For some reason, I got the idea that riding up to her house on my bike alone would impress her more than if someone just dropped me off—I guess I figured it would make me look more grown up and mature or something along those lines. It was mid-summer and I knew I could bike the three or so miles pretty quickly. I tell my parents that I’m going to see my friend right around the block, and they warn me that a thunderstorm is rolling in. I assure them that it takes no time to get there and that they need not worry.
Ten minutes later, I’m only halfway there and I’m already terrified, crying, and peddling as hard as I possibly can to go DOWNHILL against the wind. My all metal-framed, BMX knock-off was doing its best to not get hit with lightning and fuse me to its shiny silver exterior forever. More than 30 minutes after that, I finally reach my destination. I pull into her garage and thank the Lord that all the rain has hidden the fact I’ve been ugly sobbing the entire way over.
Exactly as I’m hunching over to try and catch my breath, just moments after my dramatic arrival, disaster strikes. Her parents suddenly pull in. My silly stunt had taken so long that I had missed all the potential alone time I could have had with my girlfriend. Not wanting to get her in trouble, I tell her parents that I was there because this was the only house I knew on the street and it would have been life-threatening to bike the rest of the way home in this storm.
They smiled, probably knowing it was a lie, and politely treated me to a nice dinner. That long day eventually came to an end through a very awkward drive home with her father, my bike tucked safely away in the back of his truck.
107. I Could Have Sworn This Idea Would Work
This is pretty embarrassing to admit, but back in primary school, I tried to impress a girl by constantly swearing when she was around or nearby. The point of this was to try and give the impression that I was too cool to care about rules or some such nonsense. It totally backfired though, and she ended up just thinking that I had some anger and behavioral issues.
108. Spaciously Unaware
I came from a very small, very insular, 99% white seaside town, and had very little contact with people from other countries of cultures. I’d just started university about two weeks prior to this event. There was a very attractive Asian girl on campus. One day I worked up the courage to talk to her and she was very friendly.
We talked for a bit and then I asked THE QUESTION, “So are you Chinese or Japanese?” She paused and said,”…I’m Korean.” In my insular seaside town idiocy, I’d forgotten that Asia is an entire continent, not just China and Japan. I apologized profusely and we became good friends, but I still think about this late at night and shudder.
109. Every Move You Make
In eighth grade, I was stalked for several months by a girl one year younger than me. At first, it was rather benign, we ate lunch together in our group of friends and hung out a few times after school. She seemed rather interesting if a little odd. Then it started getting creepier. She decided to read me some of her short stories which involved me tearing off her dress and assaulting her.
I was called into the principal’s office because she decided to share one of them with her English class. After that, I decided I wanted nothing more to do with her…but it just got worse. She started calling my home at all hours of the night and even stood in my front lawn from around midnight until 3 a few times. She just stared at my house. I can’t exaggerate how creepy it was.
She started writing hate mail to all my female friends calling them bad names and we got seriously worried she would do something to one girl in particular who wasn’t actually one of my friends, she was just dating a boy with the same first name as me. It all ended once I went to high school but she did the same thing to several other people before she was expelled. I don’t know what has happened to her since.
110. Wrong Turn
We were hanging out in my room playing video games. I thought she moved toward me for a kiss so I did the same. She was reaching for a different controller. It was brutal.
111. Farm Town of Brotherly Love
My younger brother has high functioning autism and it results in him not being able to understand people’s intentions. When he was about nine years old, he had a “girlfriend” who lived in our development. Our development was right next to a farm and there were always lots of sheep around. One day, this girl happened to mention in passing that she wanted a sheep.
Naturally, my brother then climbed the fence, made a leash out of rope, and attempted to forcefully kidnap a poor sheep from the farm property. There was a ram in the area, and it quickly started to chase him away. He managed to make it back out unscathed but did twist his ankle and get yelled at by the farm owners.
I had to take him over to the owners’ place to apologize, and they said they were just worried that he could have been hurt. They were very nice about it and even offered to take him into their farm to see all the animals.
112. Going All Out
In my sophomore year of high school, I went above and beyond to ask a girl out on Valentine’s Day. I ordered a bunch of red, pink and white carnations and arranged for someone to deliver them to her homeroom, thinking this would definitely impress her. I then walked by the room shortly after, only for my buddy to sadly greet me with a negative shake of the head.
Already disappointed, the girl soon came out and explained to me that she had a boyfriend and asked me if understood. She kept on asking “Do you understand?” repeatedly. In retrospect, I probably just had the “deer in headlights” look on my face. The worst part was that I was pretty confident about her saying yes and had told all my friends about it.
The train ride home that afternoon was pure punishment, as my friends razzed me about this non-stop for the entire ride. In my defense, she had invited me to her birthday party just a few weeks before and did not seem to have any boyfriend in sight at the time. So, yeah. To say I became shy about this sort of thing after that would be a major understatement.
I never realized until recently just how much of an impact that fateful day had upon my life. I have always assumed that my tendency to overthink things was just the way my personality is. Now, I have come to realize just how much of a blow to my confidence that day truly was and how much it has contributed to shaping the man that I have become.
113. I Hear a Song Coming On
I tried out for an eighth grade school musical to try and impress someone who was in it. I got the lead role and had to then spend the next four years of high school pretending that I liked theater.
114. Message Failed to Send
As much as you can call someone a stalker in high school, I had one and I always treated my “stalker” with respect even though it was weird. She would follow me around school, give me these love letters, draw pictures of us together, make me these homemade bracelets and necklaces, call me up at the most random times, she even had my private email address.
I tried to let her down easily multiple times but she didn’t give up. One time she appeared at my house crying, I had to take her in and stop her from crying. She would occasionally call up crying and I’d have to talk for hours on end to try and calm her down. One day I just had enough, so I told her as directly as possible while still trying to be nice, “I’m sorry, but I’m not interested okay…?”
She disappeared about a month later, literally left the country. Two years later she came back, I added her on Facebook and she told me she was sorry, talked to her a while and she seemed to have lost her craziness, she now has a boyfriend.
115. Can’t Chill
I’ve been crushing on the same dude for a while. It was a super-hot NYC summer and I bought a new AC and texted him, “This AC is the only adult toy we’ll ever need.” Then, he ghosted me for a year.
116. Not Strawberry Much
When I declared to my crush that I liked her. she asked me why I liked her and it was hard for me to explain. After that she compared me liking her to why people like strawberries, there doesn’t have to be a reason. Then she told she liked me only as a friend. My siblings laughed like crazy when I told them this story.
117. Worst Stare Down Ever
I was very socially awkward in grade 10 after having been a recluse on my computer for about two years. I was aware of this, however, and was making an attempt at “coming out of my shell.” As it was the first year of high school, there were many new students who had come to my school, which goes from grades 1-12. One of the new students was an overweight girl who smelled of sweat.
This new girl was sort of ostracized by people because she acted strangely like when she once claimed that she supported animal cruelty. I was not particularly fond of this girl. Some guys in my class would make fun of her and laugh behind her back, but not always so subtly. The whole thing started in chemistry class when we were going to do an experiment.
I sat opposite to her at one of the work tables and somehow made eye contact. As stated previously, I was socially inept and, as such, I decided I would be friendly and engage her in a staring contest. She stared me square in the eyes and did not budge for a second. Not once did she blink and eventually, I gave up and looked away. Not a word was shared between us that day—but it wasn’t long before I seriously regretted ever looking her way.
Later that day, I get a friend request from her on Facebook. I accepted it and thought nothing else of it. But then, no more than ten minutes after having accepted, she added me on MSN. I accepted there too and asked how she got my email. It turns out it was in my contact info on Facebook, which I promptly edited out.
She wrote to me every day on MSN and I didn’t want to block her because that would just be mean, right? She would literally talk to me any time I was online and would sometimes send me offline messages. A lot of what she wrote was: “I’m bored, entertain me,” or “I’ve been looking forward to talking to you all day,” or some random question about me or why we didn’t speak in person.
Of course, I was beginning to clue in to what was going on. One day, she confessed her love to me over MSN, to which I, to the best of my abilities, respectfully let her down. I prayed that was the end of it, but the worst was coming. The next day, I spoke to two friends about it because I had no idea how to handle the situation. Later that day, she asked me if I had told anyone about it, to which I said I had spoken to two friends about it.
She didn’t believe me because apparently two guys in my class had been pointing at her and laughing at her. I felt it was wrong to say they did it because she was fat and ugly, so I claimed I had no idea why they did that. Of course, she didn’t believe me and proceeded to spam me with variations of “I HATE YOU” and suicide threats.
The next day, she came to school with bandages around her arm, yet proceeded to talk to me like nothing happened on MSN. A few weeks after that, mid-December, she wrote and asked me if I would let her kiss me just once before Christmas. I declined, said this had to stop, and proceeded to block her.
118. Playing With Fire and Getting Burned
I was staying at a friend’s house out in the country with another friend back when we were all just 16 years old. A couple of girls had come over from a nearby town, so we decided to have a fire outside since it was still pretty nice fall weather. While outside, my friend and I both thought we’d try and impress these girls in ridiculous ways.
First, I decided to start smoking a pack. I had only recently smoked for the first time, so my body just immediately began to pretty much shut down from all the nicotine. I began to almost pass out in front of the fire when it started to get extremely hot, only to move back and then become cold instead. I was perpetually stuck in a temperature limbo.
Meanwhile, my friend decided to jump a row of chairs he had set up, hoping that it would catch the girls’ attention. He ended up getting slammed face first into the ground thanks to his foot hitting the second to last chair. Our pride was thin at that point and our skill sets were definitely re-examined the following day.
119. Won’t You Be My Neighbor?
I went on a date with this one girl back in high school. We had a few classes together and I liked her quite a bit. The date actually went really well, so I drove her home at the end. I walked her to the door, got a hug, and went back to my car pretty satisfied with everything. Well, she gives me the cute little behind the shoulder blown-kiss. So, my dumb brain decides to try and impress her by backing out of her driveway as fast as I could in response.
At this time, I was driving a 1993 S10 Blazer with a rather egregious trailer hitch. I promptly rammed into her neighbor’s brand new Honda, hitch first. My hitch hit right between the rear quarter panel and door, destroying both. This car was literally on two wheels, impaled by my lousy SUV. I haven’t talked to her since, but her neighbor is a cool guy and we actually talk frequently.
120. Don’t Go Breaking My Heart
During my sophomore year of high school, I was talking to a friend like normal while walking down the hall one day. All of a sudden, we passed by my crush, who was sitting against the wall near his locker. Thinking I could catch his attention, I started to get louder and louder and more dramatic in my rant about teachers, eventually culminating in me kneeling down and pretending to stab myself through my heart while going “AHHHHHH!!” right in front of him. Not my finest moment, to say the least…
121. A Vicious Cycle
Like many of you, I tried to impress some girls once. By the end of it, I pretty much wished I was dead from all the embarrassment. I was only 13 years old and I had absolutely no idea how to look like I was “cool” or “not a socially awkward mess” around the opposite gender. So, one day, when riding my bike at the park, my dad had called me to leave and there was a group of similarly aged girls nearby who I thought were cute. My first thought in my sub-Neanderthal brain was “Oh, in movies they like the strong guys. I can lift my bike, I’ll show that off!”
Yes, this thought actually went through my head as if it wasn’t the literal stupidest thing ever. So, I lifted my bike up over my shoulder as if it was a bag of ice or something. There was just one problem. It’s a smaller mountain bike, so it’s solid metal and very heavy as a result. So there I am, trying to act like “Me no need to wheel this thing like normal person! Me strong! Me carry bike far way! Me show!”
My dad reacts by just yelling out to me “Hey bud, just wheel it over, it’s a bike!” right in front of the people I was trying to impress. To make things worse, the way he said it made it sound as if it was a normal occurrence that I would just forget how bikes work. I promise it wasn’t! So, at this point, do I put it down and just quit this crazy scheme? Nah! I have a hole to dig and China is the destination.
I, a scrawny 13-year-old boy with a huge metal bike on his shoulder, proceed to walk slowly and carefully all the way across the playground to the car. When I finally make it there, my dad just puts the bike inside and says “it wasn’t worth it, huh?” I just stayed silent in response. My poor father probably sat there thinking “bless his soul, but he’s an idiot.” Sometimes, late at night, to this day, I am lying down calmly in bed and just as I’m about to fall asleep, I get hit with this cold feeling of anxiety and terror as I remember that moment. If I could, I would have punched myself into a coma. Darn, was I an idiot!
122. Spellbound Curse
I purposely would walk to my classes the same routes that I knew he would be. One had these set of stairs that I would pass him going down while I was going up. One day on I zoned out looking at him and next thing I knew I tripped faceplanting. My stuff went everywhere and insult to injury, he kept going while laughing at me.
Another time I saw him outside a K Mart only to zone out again and walked right into a pole with my face. He was just that mesmerizing! Seriously it had nothing to do with the mating call of a socially awkward girl.
123. Fake It til You Make It
In my university days, I had been invited to a keg race. And I don’t want to brag, but my team won. Next thing I know, everyone is up on the roof. I’m sitting up there, cut as anything, when the overwhelming need to pee hits. My drunk brain thinks, “I got myself up here! I can get down too.” I go over to the edge of the roof and see that there is about half a meter between the house and the fence with some large bins sitting there.
“Ok,” I think to myself, “gently make your way to the bin, use the fence as support, small drop down, we’re fine!” That was the plan—it turned into a disaster almost instantly. The execution was that I just stepped off the side of the roof, bounced my way down between the fence and the house, and landed in a pile on gravel right in front of the guy I had my eye on and thought was really cute.
I remember it clearly. He was just walking and a drunk girl just falls from the sky right in front of him. He went, “Oh my god, are you ok?!?” I jumped up, cool as anything, a confused look on my face as I said, “Yeah? Of course. I’m fine?” as if I do this all the time and it didn’t hurt at all. For the rest of the party, everyone kept coming up exclaiming they heard I fell from the roof.
I got my friend to pick me up and had to make him pull over so I could vomit. The next day I could barely move.
124. Pure Fantasy
It was in my junior year of high school and I was invited by a friend to attend a local dance at an all-girls school nearby. I had nothing else to do that Friday night and I figured nothing bad could happen. Yup, I was wrong about that one. During the night, this girl globbed onto me, as my friends like to say. She was not in the least bit attractive, just not my type at all.
She obviously was very into me, and I, the socially awkward penguin that I am, decided to try to talk to her outside instead. I figured if I got to know her a bit better maybe I’d somehow find some attraction. I didn’t want to be a guy who would write her off immediately because I believe every person has some type of beauty to them.
As an average guy, I’m not exactly a lady’s man, so I figured as a beggar, I couldn’t be a chooser. We exchange numbers. I figure if I’m not attracted to her, I can find a new friendship of some sort. She asks to hang out and I make it a double-date sort of deal with a friend of mine who had met a girl at the dance as well.
I realized here that me and this girl had nothing in common and that her physical appearance was simply too much for me to deal with. I gave it a shot, and I wasn’t interested. So, I didn’t make an effort to ask her out again. She, however, was waiting for me to ask her out as she thought everything was going great.
Eventually, I had to tell her I wasn’t interested because her friends were telling me to ask her out. I called her and said I wasn’t interested. This is where the tale takes a dark turn. She then goes and tells her friends that she’s going to “cut my balls off,” among various other colorful phrases. Then, a few weeks later, through some casual observance on Facebook, my friend discovered that this girl had written stories about me on her Fanfiction website profile.
He said I “had to read them for myself.” I did—and they’re burned into my brain forever. It turns out they were about me doing EXTREMELY graphic things with another man. We’re talking about descriptions of bodily fluids and my attack at the hands of another guy. In these stories, I found out that my body did things I didn’t think were possible. We discover she also had a thing for Harry Potter fanfiction, including stories about Remus and Sirius going at it while transformed.
She scared me away from dealing with girls until college and here I am.
125. Are You Impressed Yet?
I was at a bar one time and witnessed the following scenario play out. A girl with a Zelda Triforce tattoo on her hand was sitting on a stool minding her own business, when up comes a strange looking nerd boy who thinks he has hit the jackpot. Obviously, he saw the tattoo as an opening he could use to try and impress her.
So he goes up to her and starts gabbing away about Zelda and about “how cool female gamers are” in his opinion. She is clearly uninterested, but he just keeps at it. I hear him say that “us fellow gamers need to stick together, you know” and that she’s “a rare creature, indeed.” Her body language quickly shifted from “uninterested” to “screw off and die, dude!”
Sadly, he didn’t pick up on it until after he had finished telling a long, animated story about video games and she didn’t even reply. Another guy came up at that point to talk/rescue her. Nerd Boy loses it. He jumps up and calls her a fat ugly loser before aggressively stomping away. It was horrible. Half the bar went quiet.
Then it turns out Nerd Boy wasn’t quite done yet. He stomped back in to say “By the way, just because you’ve played Ocarina of Time doesn’t make you a true gamer, you idiot!” He then turned around with a huge smile on his face, confident that he had just totally humiliated her and saved his own face before leaving. I think about that guy often.
126. Unsolicited Appraisal
My very high best friend thought the following would be a smooth exchange with his crush of a long time: Goes up to this girl, and in his stoned voice: “Y-you know, your phone is absolutely worthless…” “Excuse me, why do you say that?” With a creepy grin, “Because you don’t have my number in it!” Proceeds to laugh uncontrollably.
127. Baby You Can Drive My Car
The girl I liked asked me to drive her home from school one day. I decided to not wear my seatbelt, just to seem cool. It was the first and only time I’ve ever driven without a seatbelt on. After I dropped her off, I got into a car accident. Luckily, it was just a fender bender and no one was hurt. Served me right, I guess.
128. Separated from Reality
We were seniors in high school and after a fun day together at a choral festival where I performed and he was a part of the stage crew, he gave me his number. He called the next day. We spoke for hours. He brought up that he and his dad had moved here from Florida. I asked, “Oh, really? I always thought the kids would go with the mom in a divorce.”
Then he said, “They’re not divorced.” In my horror, I just ask, “What? Is she dead?” And after a long pause he just says, “Yeah.” I wanted to crawl into a hole. I tried desperately to salvage the call, but ended up figuring I’d never see him again. I saw him the next day at school. He smiled and patted me on the head saying, “I get it. You had no way to know. We’re good.”
We’ve been married for 20 years now.
129. Movie Magic
We were in high school and she was lending me a movie to watch. We had a senior day at an arcade and she gave me the movie then. She reached into her purse and grabbed it out. I was already kind of awkward but we hugged and I left. I took the movie and threw it on the passenger seat. It rattled like candy in a box so I took the movie out of its case and found her birth control.
I knew what it was but I called her and played dumb. Her friends laughed hysterically and I just said here’s your drugs. Both of our faces were red and we walked away quickly.
130. Hairy Christmas
In high school, there was a kid who sat behind my friend in math class. He would play with her hair and whenever a hair would fall out, he’d keep it and stow it away in the battery compartment of his calculator until he had a little ball of girl hair. Then the year after, he got a pretty drastic haircut, saved all the hair in a bag, and presented it to her for Christmas.
131. Temptation Training
I was getting over a stint in the hospital and dropped a lot of weight and muscle mass during the stay. I needed to monitor my health and diet carefully so I was signed up for a program for personal fitness training and meal planning. It helped immensely and I ended up feeling better than ever down the road. However, my personal trainer halfway through became a bit too observant with my progress.
He’d make breathless observations about my legs and hips and then about my stomach. I thought it might have been crossing a line of some sort when he starting becoming more “detail-oriented” in measurements. He told me the truth one day that he felt like I was his project and that he became seriously fond of where I was going physically.
I really could have ended his job right then and there and save myself some dignity, but like the raunchy fool I am it just turned me on. I didn’t indulge in it however, but backed out of the program quietly before I got myself into a mess.
132. Wordless Exchange
I got paired with the uber-hot cheerleader for a chemistry project. I started tapping my pencil against the top of the desk due to nerves and, somehow, it flew out of my hand eraser first then ricocheted into her eye. She had to go to the nurse and hated my guts all without me saying a single word.
133. Giving Her the Shirt off His Back
So, to start with, I’m a very hairy guy. Both my chest and back are just completely plagued with hair. Believe me, it’s bad. Anyway, about three years ago, I had this huge crush on a girl. I had been telling my best friend that this girl was literally perfection in my eyes: beautiful, smart, hilarious, and down-to-earth.
The only problem was that I just could not find a way to ask this girl to hang out with me without becoming awkward and making a fool of myself. I mean, I would turn into a bumbling fool whenever I just said hi to her or made small talk, so how in the heck was I supposed to ask her out? What was I going to do? It finally hit me, though.
This girl does waxing as a side job, and I’m a hairy guy. It’s perfect, right? What if I make up some excuse and get her to wax me? Sounds like a plan that could never fail! So, one day, I send her a text and make up some reason as to why I need my chest and back waxed. Of course, she accepts the job and, next thing I know, I’m at her house lying shirtless on my back.
As she begins applying the hot wax to my chest, it suddenly starts to hit me that this might not have actually been the best way to get her to hang out with me. She applies the strip and RIP! Out comes a chunk of chest hair. I am not kidding when I say that it really, really hurt. I’m now doing my best not to show any pain, but it’s darn near impossible.
My face is obviously giving it all away, and she’s having a blast with it. Of course, I want to just tell her, “You know what, forget it! This isn’t for me after all!” But I can’t. I put myself in this situation just to spend time with her and I can’t back out now. So I just sit there and take it. Before I know it, my chest hair and back hair are both completely gone.
By the end of it, I was filled with regret, I bled a little, and my wallet was $50 lighter. I left a broken, hairless man, and I realized how absolutely pathetically desperate I was to spend time with her. I took a wax of my chest and back for that girl! However, there is actually a happy ending to all of this. We’re currently engaged to be married later this year. She loves to hold this story over my head because she finds it adorable that I took a full on beating just so I could spend some time with her. It’s mildly embarrassing to say the least, but I gladly take it because it makes her smile. If that’s not true love, I don’t know what is!
134. Doing a Stomach Stand
I was dating a gymnast back in high school. One time, we went to a park and I saw a set of parallel bars that were clearly designed for stretching. Nevertheless, I’m convinced that I can do a handstand on them because I’m awesome. She keeps insisting that they are too far apart, but I refuse to listen. I attempt said handstand, and wouldn’t ya know it? They were too far apart after all! So I collapse down, jamming my chest past my hands while straining and tearing all the ligaments holding my chest muscles to my breastbone. Good times were not had later, or for a long while after.
135. A Poet But She Didn’t Even Know It
I memorized the complete poetic works of Robert Frost. She did not care.
136. That Is One Strange Hobby…
There was a girl in my class who I had an obvious crush on when I was in high school. I finally asked her out one day and she just ignored me. I did not stop liking her though, and still held out hope that she would change her mind eventually. About two months later, we were both sitting in English class studying Romeo and Juliet. The teacher gave us all some group work that we had to do involving acting out different parts of the play.
The scene we had to act out was the one where Romeo gets rejected by the girl he was into at the beginning of the story, Rosaline. While all of the groups were hard at work, I overheard my crush saying to her project partners that she really wanted to play Rosaline in their skit. I then heard her say to her friend “I like rejecting guys, it’s so much fun!” Umm, excuse me??
I couldn’t believe my ears and I instantly lost all respect and feelings for her. What kind of a cruel psychopath do you have to be to actually enjoy hurting other people’s feelings?
137. It Was a Match Made in…
In terms of real life, a buddy of mine was talking to this girl we all knew, and they’d been getting pretty flirty. So, the decision was made to invite her camping with us in the hopes one of them would make a move. Flash forward to that night and our buddy did seemingly everything he could to screw it up—spilled beer on her, stuck his finger in her mouth for no reason while she had a look of what the heck is going on here.
Finally, somehow, she still didn’t hate him and toward the end of the night, he tried to kiss her and headbutted her pretty darn hard because he moved in too fast. After this, they had a talk because this girl was apparently the crown princess of second chances, and he threw up on her. Obviously, this was God’s way of intervening.
138. I Just Came to Say Hello
This was a while ago in high school, so I don’t know if I can really fault him for being an idiot—but he told everyone we knew that I was his dream girl and that we were going to get married someday. He actively sought out rumors about who I was crushing on, or who was crushing on me, or just about pretty much any guy who would talk to me.
He would then approach them and ask them to please, please, please let him have a chance and to not ask me out. The weirdest part was that I barely even knew this guy, and didn’t even really talk to him much to begin with. I didn’t even know his last name! Our whole relationship was literally just saying hi to each other during calculus class every morning.
139. Can’t Get Too Close
I asked her out, and she said yes! Then, she dumped me after two weeks, saying she didn’t want to start anything new because she was moving next month and didn’t tell me. The time came for her to move and I nearly lost it when I found out where she was moving to. Girl was moving into my house!
She was dating my roommate who looks eerily similar to how I look and could be my twin. Like, we often did get mistaken for brothers. So, she moved in and started a committed relationship with him. There were some thin walls in that house too.
140. Scroll On If You Dare
I had a huge crush on this one girl in my college English class back in my younger days. She was a bit religious and I wasn’t, but she didn’t talk about it too much so I didn’t mind. We used to talk all the time and we even did a few projects together. Then I found out that she was no longer dating this guy she had been with for a while, so I decided to try and pursue her myself.
However, when I looked her up on Facebook, I found a whole bunch of weird posts she had made encouraging prejudice and fights against certain minority groups, as well as a post about how all of the school shootings in America have been happening because we no longer allow religion to be taught in schools. It took a few more scrolls to get to the prejudiced stuff that I just knew would also be there at this point. Let’s just say that these discoveries were a major turn off and disappointment.
141. Well, Look Who Decided to Show up
I had met this girl at a bar and we hit it off. We were making out and all was good. I got her number and we agreed to meet up later. I set up a date with her for a few days later and an hour before the date she canceled on me. A week later, we set up another date and she canceled that one as well just a few days before. At this point, I’m not about to waste any more time and I’m done.
Well, a couple of weeks later, she calls me and says that she is going back with her friends in a few hours to the same bar we met at and that she wants to see me. I say sure, so she asks me to text her before I leave for the bar. I text her and tell her that I’m on my way, and she says that she is too tired to go and is deciding to not go after all. I decide to say screw it and I just go by myself.
Well, guess who I saw show up at the bar a couple hours later with her friends, just having a blast! That was when I instantly lost all interest in her. I sent her a text message calling her out on her BS and informing her that she was a piece of garbage. I then blocked and deleted her number. I have not been back to that bar or heard from her since. Here is the really funny bit, though.
That first night, she said that the only reason she didn’t want to go home with me was that I seemed like a ladies’ man and like I probably took lots of girls home with me constantly. The truth is that I was a virgin at the time, but I had just lost a ton of weight and I was finally comfortable with my body and approaching women as a result. I guess I just overshot my confidence this time. Oh well, live and learn!
142. Bad Sense of Humor
I had a big crush on this one girl from my school, and she was definitely aware of my feelings. She seems to have felt the same way about me, as she decided one day she was going to do something to try and impress me. What did she decide to do to try and impress me, you ask? She went up to a smaller kid and started making fun of them right in front of me, then looked over at me for approval.
What she didn’t realize was that this smaller kid she had picked out for ridicule was actually my little sister. I guess she didn’t know that we were related because we have two different last names. What she did would have been bad enough if she had been making fun of any kid, but there was definitely no way I could ever view her the same again after witnessing this particular incident go down.