Heartbroken People Share Stories Of Crushes Gone Wrong

Samantha Henman

Ahh, the sweet feeling of a genuine crush. It can go one of a few ways. Ideally, it all works out perfectly and is reciprocated—but as we all know, life doesn’t always go the way we plan it. Here is a collection of real-life tales of crushes lost in an instant and stories of people who went embarrassingly far to impress a crush. When we have a crush, we lose our minds a little bit, and this list more than proves that to be true. Buckle in for some serious cringe-inducing moments with these heartbreaking tales of crushes gone wrong. 

1. 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…


2. All Except for One

A dude was trying to make me jealous by saying something along the lines of “I can’t be ‘just friends’ with girls, they all have crushes on me!” I stopped crushing on him out of spite right then and there.


3. 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 police and citizens. I got tear-gassed and robbed. He was not impressed.


4. Food Fight

What turned me off of my crush was the way that she chewed food. Sounds shallow, I know, but it was just not something that I wanted to have to hear for the rest of my life. That, and that she snacked on ketchup packets. She even kept a stash of them in her glove box. She would just tear one open after another and suck them down. Whole lotta nope!


5. The More You Nose

In elementary school, I really liked this girl. Like, huge crush. 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.


6. 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.


7. 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.


8. This Relationship’s Diagnosis: Negative

I stopped liking the person I was interested in when she started endlessly spewing crazy and unscientific conspiracy theories about how vaccines cause autism. Don’t believe everything you read on the internet, people! You’ll become that girl!


9. 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.


10. Turning Her Inside Out

I stopped liking my crush when I spent a little more time around her and started to realize that she was a legitimately mean person. Like, she was just really cruel in the way she treated other people. In my eyes, she went from really hot to not looking very good at all faster than you can even imagine. One of my friends ended up dating her and I just could never see anything even remotely attractive in her anytime I saw them.

She became what my friends call “Ugly Hot”—as in, she’s so ugly on the inside that it affects the way people perceive her physically as well.


11. 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!


12. 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.


13. 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!


14. 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.


15. 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…


16. Table for Two, Dinner for One

Me and the guy I had a crush on for the longest time finally went out together for a dinner date one night. I ended up spending most of the time at the restaurant by myself while he stayed in the bathroom feeling like trash because, unbeknownst to me at the time, he had apparently been suffering from withdrawal problems due to oxycodone painkiller addiction.

I guess someone had brought him some or something while he was in there, because he came back all of a sudden after a long time—now feeling great. He invited me back to his place and stupid me agreed to go along, but I almost immediately regretted it and realized that my feelings for him were now gone.


17. 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 died 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 headfirst 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.


18. Beggars Can Be Choosers—But Not Without a Cost

In my case, the person was my girlfriend. She had been searching for a job for over two months. All the while, I had helped support her in every way as she endured the long and difficult process of unemployment and a job hunt. Then, when she finally received a pretty solid job offer, she turned it down because she felt that her interviewer was rude to her.

By rude, she meant that the interviewer was upset that she had shown up more than 20 minutes late for the interview. This incident and the way she handled it honestly just opened up my eyes to both her immaturity and to how little she was appreciating all that I was doing for her. I broke up with her shortly after.


19. 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.


20. All Fluff and No Substance Makes Jill a Dull Girl

When you really like someone, it’s very easy to dismiss the things that would be obvious red flags under any other circumstances. My worst crush of all time was a vague kind of girl, always posting ambiguous romanticized crap on social media like one of those Tumblr love quotes. On our first date, all she talked about was her online admirers.

At one point, she told me not to worry about them. I hadn’t been worried at all, and had no reason to even care—they all seemed pathetic and had her on a pedestal as their hero. Then I realized that she had nothing going for her in her life. She still lived with her parents, had no clear life goals, no burning passions that showed, no interesting hobbies, was failing her studies, and didn’t even seem to be trying.

This realization just hit me all at once like a ton of bricks, and my feelings for her suddenly changed. It was as if a huge veil was suddenly lifted away that had been covering my eyes for the entire time I had been interested in her romantically. They say that a pretty face is enough to get a guy hooked because that’s all that really matters to guys in the end.

I would say that that statement is not fully true without one particular caveat—quality guys who are serious, self-respecting individuals will only put up with nonsense for so long before they nope right outta there if the girl doesn’t have anything else to back her good looks up with.


21. 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 up smoking 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.


22. 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 hell 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 hell 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 crap 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.


23. The Game of Love

I intentionally threw multiple games of Uno to let a girl think she was amazing at the game.


24. An Unhappy Ending

After a failure of a date, the guy I had liked up till that point attempted to make out with me and eventually ended up climbing on top of me against my will. I was so not into it that I started telling him no and pushing him off, but he just started to fight me and kept angrily trying to persuade me to change my mind by saying “Come on, I’ve been waiting for this for a long time!”

Eventually, I started shouting “No!” even louder, until he finally just gave up and let me go. He was very pissed, so I just grabbed my things and left. Let’s just say there was no second date…


25. 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!


26. 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.


27. 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.


28. Praying for Better Judgment Next Time

I went to a fairly large college in a Bible Belt town. There was this student group on campus called Christ’s Ambassadors, whose members would all wear matching shirts on Wednesdays. They would often hand out mini-Bibles to students on campus, and tell them that they were all going to hell. Let’s just say that this group did not quite represent my personal values.

That same year, I had a huge crush on this beautiful guy in one of my classes. Then, one Wednesday, he walked into lecture wearing one of those darn Christ’s Ambassadors shirts and my heart literally broke in half on the spot. In an interesting plot twist, though, a pretty good friend of mine ended up marrying him and he turned out to be extremely physically abusive.

Needless to say, that fact has helped to quell the remainder of my crush quite a bit as well. Thankfully, my friend has since gotten out of that marriage and is now perfectly safe and sound.


29. 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.


30. Like Father, Like Daughter?

I know this may sound a little unfair, but for me it was getting to know the girl’s family that made me lost my crush on her. To give some context, I had this insane vegan girlfriend with a mentally unstable sister. I had no idea why this sister always seemed to act so rudely towards me, and when I asked about it I was told that it was because “She didn’t want me to think we were friends.”

Her mom was very nice, but her dad didn’t like me because he thought some of my mannerisms were weird. Sorry for being high functioning autistic, but there isn’t really anything I can do about that. As if that wasn’t enough already, the family was also obsessed with pets. They had 13 cats, three birds, and two dogs. They also believed in ghosts and would all sleep in the same bed whenever they thought the ghosts in their house were being extra uppity.

As soon as I came to realize that they were the weird ones and not me, my feelings for the girl just started to disappear.


31. 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.


32. 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…


33. 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. 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…


34. Who Can Really Define True Greatness?

I started to lose respect for my crush when he started to constantly talk to me about how great he was and how much better he is than all the other boys around. Unsurprisingly, he turned out to be the type of person who really only cared about himself. Oh, and by the way, he was not actually that great, nor was he better than everyone else around like he made himself out to be. Just sayin’!


35. 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.


36. But Words Will Always Hurt Me

When I was in third grade, I had a crush on an older boy who was already in middle school. Then one day I heard him say a bad word, and 7-year-old me could never forgive him. My crush disappeared instantly. In case you’re wondering, the word was crap. I definitely dodged a bullet on that one!


37. 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.


38. Tooning Out of This Call

I was fixed up with a guy that I never knew too well to begin with. The first time we really talked was when we spoke on the phone for three hours. He kept quoting the cartoon Naruto and said he was striving for the best in his life because “that’s his nindo way”. He must have said this line at least 10 times, along with many other random quotes from the show.

After a while, it was getting really annoying. So, as lightheartedly as I could, I made a rule that neither of us could quote anyone else from that show or elsewhere from this point on, and we would both have to stick to only original thoughts for the rest of the call. He literally struggled and could barely think of anything to say. It became too much for me to handle and I lost interest.


39. 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!


40. 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 butthole. There were toilet paper remnants visible. I disappeared from that theater real fast!


41. 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 try and impress her. I bravely 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.


42. I Guess She Walked Right Into That One…

I had a huge crush on this one girl for a really long time when I was young, and in my eyes, she could do no wrong. That is, until the day I was talking to her and she decided to start speaking badly about someone we both knew because she saw them with crutches. This person was on the crutches after having sprained their ankle falling on a trampoline.

Despite this, my crush made fun of them and even went as far as to seriously claim that they were just doing this all for attention and were not actually hurt that bad. There was no way I could let that kind of disgusting behavior slide. Seriously, if you don’t have anything nice to say, don’t say anything at all!


43. 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.


44. How to Muddy the Waters

Back when I was a teenager, my friends and I used to often go on dates as a group. It was a pretty common thing to do in my social circles at the time. Anyway, there was this girl who I had liked a lot for a pretty long time, so when I finally mustered up the courage to ask her out, I brought her along on one of these group dates.

As we were all walking down the street together on the way to where we were going, the girl slipped and fell in some mud. Now, the correct thing for that girl’s date to do in that situation would be to help her out and make sure she’s okay, right? Not for this immature teenager! My only thoughts as I watched it happen were how unattractive she looked with mud all over her and how I didn’t think I liked her anymore.

Not only did I fail to come to her aid in her moment of need, but I also ended up basically ignoring her for the rest of the day and just talking to my friends instead to avoid the potential second-hand embarrassment. I feel pretty mean about my behavior in hindsight, but at the time I felt it was totally justified because the mud was a massive turn off.


45. 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 insane 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 tough 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 huffy 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, 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.


46. Getting to Know All About You

What ended my romantic feelings towards my crush? I actually spoke to them for once! It turned out that, although they are definitely a great person, they were just not even half as interesting as I imagined them to have been in my head. It’s funny how we do that, isn’t it? We build things up in our imaginations to be just the way we want them to be, and meanwhile, we don’t even really know those things at all.

In this case, it was my crush that I did this to, but it could be done to almost anything or anyone. Oh well, life goes on!


47. 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.


48. The Best Fish in the Sea

My boyfriend would constantly insult all kinds of things he knew I liked, and would also constantly tell me how much better he felt his opinion was than mine or anyone else’s. You seriously have to ask yourself what makes a person feel the need to act like that, as if they just need everyone to know exactly how much better they feel they are than all the rest.

Definitely not boyfriend material in my book, and hopefully not in yours either. Despite what they would have you think, there are definitely way better people out there!


49. 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 hell, 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 gun-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.


50. Swimming Against the Current

I stopped having a crush on a guy when I discovered that he enjoyed picking on my slightly autistic classmate. We were all in high school and he was a year older. He was a star breaststroker on my summer swim league team. I’ve always thought that swimmer guys were cute, and I first started to develop feelings for him during those swimming sessions.

The crush lasted a few years until we wound up both on the same high school swim team. Then one day he started mocking my classmate right in front of me. It was nothing blatant that could be concretely classified as bullying, but it was clearly condescending and insensitive. To this day, I still can’t look at him without thinking about that behavior.

He’s still considered the perfect young man in the eyes of our community, but it’s how you treat those who cannot defend themselves that truly defines who you are as far as I’m concerned.


51. 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.


52. Good Intentions, Bad Result

I lost my feelings for my crush when he asked me if my family had considered looking into essential oils and vitamins as a cure for my dad’s stage IV cancer. I appreciate the thought and I know he meant well, but I could tell in that moment that he and I just fundamentally don’t view the world the same way and, as a result, it could just never work in the long run.


53. Bad Hair Day

When I first started to like the man who has since become my husband, I thought he’d be impressed if I radically changed my look. So, I dyed my hair—and while I was at it, my eyebrows too! I looked like a total freak, but I thought he would find it cute. Not sure what was wrong with me back then, but thankfully we still managed to get together in spite of all this silliness.


54. 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.


55. 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 of cigarettes. 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.


56. A Little Self-Reflection Can Go a Long Way

When I was a young lad, there was a girl who I had a huge crush on. After trying for a while, I was finally able to take her out on a date one evening. Now, this girl really liked to talk about herself—you can almost say it was one of her favorite pastimes. I am personally more of the listener type to begin with, so I did not think that this would be an issue for our potential relationship.

During one such self-praise session at our date, she said something along the lines of “I don’t know why, but everyone just keeps ending up having a crush or me, some of them even end up thinking they’re in love!” I immediately thought to myself “Do I seriously want to listen to nonsense like this all the time?” The voice inside my head came back at me and said something like “Bro, you don’t even tolerate nonsense that’s half this crazy from your family, are you really even asking that question?” And that was the end of that association!


57. Road Trip

I drove all the way from Virginia to New York to pick up a girl I liked from one of the local airports, which was about an hour or so away from where she went to school. But, when all was said and done, I got the girl! So it was well worth it in my book.


58. Not What You Expected

I had a crush on this one girl for pretty much all of high school. I was never able to make anything come of my feelings and I eventually ended up going to my senior prom solo. One of this girl’s friends was also there alone. I danced with the friend for most of the night and had a lot of fun. Eventually, we did the whole swap partners thing for a dance and I found myself suddenly dancing with my crush.

Garth Brooks’ “The Dance” was playing and everything was exactly how I had always imagined a perfect moment to probably be like. Then, all of a sudden, as I was looking into her eyes, I realized that I had built her up in my mind to be more than she actually was. My feelings for her died right then and thereafter four full years of inner torment and desire.

Ironic, isn’t it? And no, I didn’t end up getting with the friend and I’m still socially awkward to this day.


59. 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.


60. Smell Ya Later!

I lost my feelings for a guy when I caught a whiff of his breath one morning. It took me out at the knees, and definitely not in a positive way!


61. 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…


62. How to Mutilate Your Reputation

I saw my crush arguing with someone over the topic of female genital mutilation practices that take place in other parts of the world. I know you’re hoping he was the one on the right side of this issue. Sadly, he was not. He was trying to defend the idea that mutilating a young girl’s body against her will is perfectly justified. I mean, wow was that a fast crush-kill.


63. 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 sex. 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!


64. This Smells Like the End of a Beautiful Relationship

There was this girl in my office who I thought was cute and had a really big crush on for a very long time. Then one day, I was passing her in the hallway and she crop-dusted me. For those who don’t know, crop-dusting is when someone farts as they walk by you, leaving the remnants of the smell and sound behind as a souvenir.

Needless to say, I pretty much lost all my attraction to her at once when that happened. She was definitely not the one for me!


65. What’s Up?

Before we met, my boyfriend had feelings for another girl. So what was his plan? Never make eye contact or acknowledge her existence. He started looking above her head whenever she talked to him, slowly looking higher and higher. At one point, he was staring directly at the ceiling while this poor girl talked to him for a good 15 minutes.

After that, she thought he was weird and never talked to him again.


66. Man’s Best Friend Was This Girl’s Worst Nightmare

I was really into this girl from my high school until the moment she decided that she was going to have her dog put down before she left for college because she didn’t believe that anybody in her family could take care of him as well as she always did. It was an English sheepdog and, somehow, this girl did not see any of the irony or absurdity in what she was doing.

Of course, it was probably hard for her to understand my attempts to explain it as I was pretty much incoherently screaming in her face the whole time. I literally did not know how else I could possibly react to something that outrageously stupid and sad. And for the record, the girl did, unfortunately, go through with this plan in the end. RIP little critter, I sure hope you’re in a better place now!


67. 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.


68. 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?


69. 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.


70. When the Internet Meets Real Life

I really liked this guy and was hoping to make something happen with him. As things started to progress, my curiosity led me to start checking out his social media accounts to see what kind of stuff he had on there. I discovered that his Facebook profile had a photo album specifically designated for posting photos of hot bikini models in on a regular basis, and I found that pretty weird.

Then I started reading his bio and comments and other stuff—whatever I could find. The way he wrote online made him come across like an immature and awkward 12-year-old boy, even though we were both grown adults at the time. He even used a lot of emojis in all of his writing. Seeing this instantly killed my feelings for him and I could not ever see him the same way again from this point on.


71. 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.


72. May God Have Mercy on Your Soul

He interrupted something I was saying during a perfectly lovely date because he said he had to tell me about something serious. My reaction, naturally, was “Of course! Go ahead!” That “something serious” turned out to be a monologue about his personal relationship with Jesus Christ. I am not a religious person and I am not interested in dating anyone with different values than me, so I knew right away that I was no longer interested.

I interrupted his speech at about the 10-minute mark and let him know that we should just end things between us because we were incompatible. His whole face changed into a terrifying expression and he decided to spend the next half hour trying to save my soul from damnation. The night ended with me literally running down the street while he chased after me screaming about the power of Christ’s everlasting love. We’re both dudes, by the way. And we had already slept together.


73. 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.


74. Broken by the Five-Finger Discount

He would steal people’s tips off the bar counter when we were at a bar together with friends. Then he would offer to buy me food with it. No thank you.


75. A Poet But She Didn’t Even Know It

I memorized the complete poetic works of Robert Frost. She did not care.


76. Listen to an Expert, Honey

Not so much a crush, but we were in the initial sentences of the conversation getting to know each other. We were describing to one another what our jobs were. He corrected me on describing my job… stopped right there, said it wasn’t going to work out and ended the conversation…


77. 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!


78. Too Cool for School

I had a crush on a guy in high school who was a little bit of a rebel. Nothing serious but definitely had a bad boy thing going on. One day in class, the teacher told him to do something minor and he flipped out, basically had a temper tantrum and refused. Totally killed all interest by being a jerk for no reason.


79. 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 hell 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!


80. No Flake is Just Like the Other

Said she would turn up on a date, then flaked. Told me she had been called into work urgently. I said ok that’s cool. Second time she flaked again said that she had to tutor someone. Which made no sense because…would you not have that planned?


81. How Can This Possibly Go Wrong?

Middle school. Cute Guy was overheard saying that he was impressed because a girl he knew had farted 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 fart 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.


82. The Tough Customer

We were eating dinner out, and he was rude to the server. Told him (we were pretty close friends) it would be nice to add a “please” or “thank you.” He said “Why should I? She’s a waitress (implying he feels superior), and I pay her to do her job.” Instant turn off, and didn’t really want to hang out with him, even as friends, after that incident.


83. 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…


84. In the Doghouse

A woman I was talking to was recently divorced and had moved back in with her parents. She already had a child and a couple of pets and was talking about getting another pet and her parents told her no, she chose to go ahead and get another pet anyhow and basically her parents began pushing her out the door. And it was a stressful situation for her, and I suggested she talk to her folks.

However, once she told me she was grown and made her own decisions and did not care about their rules, I suddenly understood, and quickly lost interest.


85. Diving Right in

Me, 15-16, gets invited 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.


86. Time Flies When You’re Too Young To Be Serious

I went on two dates with a girl when I was in college. She was wonderful but immediately wanted to be “official” and started drafting Instagram posts about “us.” She wanted to spend every day together and have sleepovers every night. it was so out of nowhere and we literally knew nothing about one another. I tried to look past it, but she asked me to be her first and I got uncomfortable.

She seemed naive and I didn’t want to take advantage. I suggested we take things slow and she took offense. I cut things off and her reaction was super childish. All of this in a 3-week period. Sweet girl but the pacing was off.


87. He Stopped Loving Her Today

I pretended that I enjoyed country music. Never again.


88. Snail Mailed Out of Love

Back in college, I was seeing a girl casually. Whenever we’d text, she’d take hours to respond to any message. It wasn’t a big deal since most of the time it was just chatting or setting plans for the following weekend or something. It was a little annoying because it’d take a full day or two to set up plans because of the slow responses, but whatever.

I’m a bad texter so I can’t really judge someone for that. But I started to notice that when we hung out together, she’d immediately respond back to any and every text she got. She had some loud song as the ringtone that played for like 15 seconds and set it so that her camera LED would flash constantly while it rang. Totally obnoxious and made me really notice how often she texted.

I casually asked her who she was texting one time and it was just some friend from school that had sent her a meme. After that, I realized it wasn’t going to work. Being a slow texter is fine. Constantly texting while hanging out was annoying, but not a deal breaker (especially if we were just chilling at one of our houses). But the realization that this person who was glued to her phone but didn’t feel like it was a priority to respond back to my texts made me feel unimportant so I kinda just drifted away.

We stayed friends because we shared the same group of friends and it wasn’t awkward or anything. I just stopped trying to do things with just the two of us.


89. Common Lack of Interests

Back in college, there was an amazing girl who lived across the hall from me who was drop-dead gorgeous. This was when iTunes library sharing was super popular and pretty much everyone in the hall had their music library connected to the internet. Everyone on the floor could see your music library and listen to your songs.

I creeped the hell 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…


90. She’s Not Worth the Investment

Met a woman, thought she seemed cool. We went out to eat, she’s telling me about how she fell on financial hard times and moved back in with her parents. The way she described it, just sounded like she got unlucky, not that she did anything irresponsible. It happens. When the bill came, I told her I’d pay. She said, “Thanks, I appreciate that, I’m trying to save my money right now.”

I said, “Sure, I understand, you want to get your own place again.” She said, “No, actually I mean I’m trying to save up $500 for a tattoo I want to get.” I’ve got nothing against spending money on tattoos, but when you’ve just spent a first date talking about the financial troubles you have, maybe now’s the time to start putting money away for necessities, not tattoos.


91. 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.


92. Bearing All Too Soon

Finally took me out on a date. To a dirty strip club. Not one of the fancy ones, but the smelly gross ones where they clearly don’t have high standards for who dances there. I watched a girl get sent home because the oscillating fan that sat in front of her was blowing dirty stank all over the place. He knew all their names and they knew his.

Weak power moves though, because he got mad that most of the girls congratulated him on being able to get me to go anywhere with him and asked him why he took me there instead of some nice dinner. He got mad and took me back to my car. I didn’t even have to get upset over the deal because he did it to himself. Never talked to him ever again.


93. Personal Sacrifice

I intentionally fell off the slide in grade four to try and attract someone’s attention. My right shoulder still regularly hurts 12 years later…


Stupidest Things to Impress Crush factsShutterstock

94. 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.


95. What a Croc!

I swam across a river filled with crocodiles. 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 to impress crushes, just talk to them—even if swimming across a crocodile-filled river seems easier.


96. We’d Just Be Out of Pitch

I was crushing on this girl from afar for a while. We were on the same military training base. One day, my friend Drew and I were eating lunch and the place was nearly full. It just so happened that she had come to lunch at the same time, and she and her friend ended up sitting next to us. Drew knew the score and gave me an excited “Good luck buddy!” look.

I was just about to introduce myself: my mouth was open, and the words were about to come out…when she started talking to her friend. Her voice sounded like a high-pitched Roseanne Barr. I closed my mouth and turned to give Drew a “I think we’re done here.” look, but he was too busy silently laughing at me to notice.


97. Securing Your Place in History

In middle school I gave this girl I fancied a necklace from one of those 25 cent machines at the store. The necklace said “Love” on it. I felt really really dumb about this for nearly ten years. About a year ago, I went and visited her, and to my surprise, I found it on a wall full of memorabilia from her life. I find it quite touching that she held on to it, even if she only kept it as a funny token.


98. 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 ass 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.


99. A Story With a Moral

In high school, at a school of about 1,500 students, we had a homecoming pep rally in our gym which included a basketball game called Bumpout. The winner won two tickets to the homecoming dance. Needless to say, I came out victorious and, as the entire school was cheering (for some unknown reason because I was very shy and unpopular), I ran up to the guy hosting the rally, took the mic out of his hands and blurted out “Hollywill you be my date to the dance?”

The gym went silent, and then all of a sudden–to my enormous surprisea “YES!” came out of the crowd. Fast forward eight years and she’s now my wife and the mother of my two-year-old son! Sometimes publicly crazy, impulsive, non-thought-through behavior works!


100. 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.


101. Strike!

Knew a guy who went to a bowling party with a girl he had his eye on. 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, breaks girls nose, blood everywhere.


102. Their Tragedy Is His Inspiration

I was living in the university dorms at the time, had a crush on a guy in another dorm. One day I was heading outside and found him posting pictures of concentration camp victims in the stairwell. I was like what the heck, and he got really angry at me for being in my own dorm that he didn’t even have access to. Never got an explanation for the creepy pictures.

It came out later that he was also using rock climbing equipment to scale the walls and creep in people’s windows, so dodged a huge bullet there.


103. 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.


104. A Matter of Love and Faith

Had a crush one a girl once in high school, we had a class together and were lab partners, and talked about all kinds of stuff. I was big into rock climbing at the time and she had never been, so I invited her to go with me to the gym one day, she was totally excited… everything was looking great. Then the next day she told me her parents said no because I wasn’t Mormon, and unless I wanted to convert, she couldn’t go out with me. Yup, that’s all it took.


105. Schooled

I pretended to struggle with Intro to Calculus just to get the sympathy of a specific girl. It then turned out that one of her best friends was the girl I tutored in Linear Algebra…


106. 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.


107. 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.


108. This One’s a Nailbiter

When I was 12, I started biting my fingernails because I thought that would bring me closer to my crush who also had a nail-biting habit. Obviously, that didn’t work out, and here I am at 21 and still biting my nails.


109. 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. Hot damn, 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.


110. 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.”

Must have worked, we’re married now.


111. Make Sure You’re Sitting For This One…

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).


112. 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.


113. 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…


114. 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.


115. 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.


116. 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…


117. 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.


118. Time to Start Singing the Blues

I burned her a mix CD of love songs. Her friend then asked me if I liked her, and I panicked. Trying to play it cool, I was like “Nah, that’s just the music I like to listen to.” She ended up dating my friend instead.


Stupidest Things to Impress Crush factsPixabay

119. 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. We ended up being together for the next two years though anyway.


120. 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.


121. 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 eight 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.


122. 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 racism and violence 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 homophobic 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.


123. Keep It to Yourself

She wasn’t a very social person and didn’t get along with people. I took her to a Thanksgiving family gathering and at one point a little cousin of mine walked passed her and she mentioned out loud that she hates that little girl and how annoying she is IN FRONT OF THAT LITTLE GIRL’S SISTER WHO IS SITTING RIGHT THERE IN FRONT OF HER! She was just very rude and had no social awareness. Sorry, family comes first and even though I don’t like some people I don’t say it in front of everybody and be rude about it.


124. 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.


125. 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 crap. 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!


126. Fart Failure

Twelve 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 fart to get their attention. Bending over in the middle of the doorway, pushed one out. Pooping.


Sources: 1, 2, 3, 4, 56, 7, 8, 9, 10, 11

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