scorecardresearch

Awkward Crush Moments That We Can’t Stop Cringing At

J. Hunter

Everyone has a story or two about crushing on someone or being the “crushed” suffering from one-sided unrequited love. You don’t have to cringe too hard at your awkward crush moment after you read these Redditors’ stories about their awkward moments with their crush or someone crushing on them.


1. 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.

linoodl

2. Lovesick

One day, my step-sister invites me to her birthday party. I go with my best friend who’s also her friend. The party goes on and my step-sister tells us her best friend, a random guy from my school, is finally coming and bringing a friend. Of course, he’s bringing my crush from high school who’s older than me. We didn’t have any friends in common, so I had never tried to talk to him before.

But still, I was glad he’s at the party because I could finally talk to him and try to flirt! He got there and told us he had weed. I don’t really smoke but it was a party and I wanted to be in the same mood as him.  We go outside—me, my best friend, my stepsister’s best friend, and my crush. We smoke. I take TWO puffs.

I was caught in a bad trip all night long, sat on a chair and never stood up until I got to bed. I didn’t even see my crush leave.

ultramoth

3. To the Moon and Back

There was a time that I thought I could impress her with all the facts I know about space. Apparently, making word vomit with space facts does not make up for good conversation on a bus during the ride back with no other available seat. My constantly trying to salvage the situation with more space facts did not help.

JustSpaceSmut

4. 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!

schlab

5. 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.

Loud_Mouth_Soup

6. 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.

HungryLikeTheWolf99

7. Snappy Schoolgirls

As a young, male teacher, I’ve become used to students having awkward crushes on me. The most awkward part of them is when a student will come up after class and show me all the snapchats other students have sniped of me during the lesson.

jeremytheboss

8. You’re the Boss

I’ve been working in an insurance agency for about 2.5 months. For about two months now my boss has been acting very “affectionate” towards me. By that, I mean she’ll call me a dork in a flirtatious manner. One time she told me that if I stayed late, she’d buy me dinner, or she’ll slap me playfully when I say something mildly witty.

There’s also when I show her something on my computer, she’ll kind of lean on the table but lean on me also a bit at the same time, and she’s recently started a habit of affectionately punching my arm. It’s making me feel really awkward and I don’t know what to do about it. But it’s okay, as long as the fact that she could be crushing on me means that I have an easier time at work.

brrrrrrat

9. 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 and we got detention.

eggedshrek69

10. 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.”

MagicJasoni

11. 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.

lemurriot

12. 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.

lol_catd

13. 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.

TheyCallMeShxxHead

14. 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.

dbeey270

15. 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.

I_Cant_Scream

16. 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.

Tasadar

17. 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.

CafeConLecheLover

18. 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.

xXWarriorAngelXx

19. 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.

cherryblahsum

20. 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.

Permalink

21. Camera Shy

Last weekend she wanted to take selfies with me at a birthday party and, for whatever reason, I always make the weirdest faces when I know my picture is being taken. She got frustrated and just gave up. I’m going to ask her out on Saturday though so wish me luck.

Damnthatgraham

22. 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.

__Pyrix__

23. 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 the police.

Permalink

24. One Swift Move

We were at her place and she’s sitting on the couch and with her purse next to her. I grab her purse to move it so I can sit next to her and then some tampons fall out. She quickly gets up and puts them away. I’ve never seen her move so fast before.

realme857

25. “Seen”

One time I wrote my crush, who also happened to be the new kid in school, a letter and he never responded—turns out he was also my new neighbor! As if I didn’t learn from that mistake, I wrote my number down for someone I thought was cute in college and he ignored it. Then we ended up getting assigned seats in class and had to sit next to each other the rest of the semester.

this_couldbeyou

26. 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.

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.”

superdude4agze

27. 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.

apocguy

28. 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.

Briggsnotmyers

29. 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.

ThatJoeyFella

30. 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.

elleira-16

31. 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.

Musashi10000

32. 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.

memymineown

33. 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.

maximillious

34. 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.

TheTrollScience

35. 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.

blackaubreyplaza

36. 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.

Hereva

37. 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.

Tsunderella

38. 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.

Lorna_Dane

39. 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.

miss_beat

40. 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, rather rotund in nature.

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 fetish 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.

applcmptrdood

41. 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.

RallyCow

42. Don’t Go Breaking My Heart

In elementary school, there was this girl who would constantly get beat up by this kid. He would torment her every lunch. I saw this a few times and saw that she was defenseless against him. I wasn’t a big kid, but I was bigger than the guy beating her up. I ended up fighting him off of her a few times. I even pinned him down and let her punch him. He stopped picking on her after that.

Then in junior year in high school, I’m at winter formal and I’ve already split from my date. We weren’t really interested in each other at all, we just went with each other so we could go. She’s standing alone and it turns out that her date ditched her. I end up taking her to the dance floor and dancing with her. We hit it off and just have fun on the dance floor.

We ended up hanging out later and I learn that she has been crushing on me since elementary school. She had built this image of me in her head as her prince charming/white knight. I never did those things with the intention of getting laid. I just didn’t like seeing someone defenseless and being picked on like that.

She was decently attractive and a nice girl, so I just went along with it. She eventually realized at some point that I was not as into her as she was into me. She told me that she is fine with just hooking up and not letting it get serious. We start making out and things start to get crazy. She suddenly tells me to stop. I stop.

She then says that she doesn’t want to go through with hooking up with me. She explains that she had built up this fantasy of it in her head and she didn’t want to ruin it with reality. I told her that I understood and I took her home. I cut contact with her because I realized that I’d just be using her if we hooked up.

It wouldn’t have been cool for me to mess with her emotions like that. I already did it enough already.

lilhurt38

43. 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.

AnikansWeakAs_

44. 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.

stineface

45. 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.

TheDebauched

46. 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.

calteg

47. 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.

deepvape

48. 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.

Honic_Sedgehog

49. Crushing Defeat

After a long silence, our conversation started with me saying, “So…haha, how do you start a conversation with someone?” Then she was like, “We’re talking right now, aren’t we?” I didn’t know what to say and after a minute of more silence, I just walked away.

Zakkumaru

50. Hardheaded

I still cringe when I think about my first solo date back in high school. 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.

-eDgaR-

51. 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.

Permalink

Sources: 1, 2, 3, 4, 5, 6, 7


Factinate Featured Logo Featured Article
My mom never told me how her best friend died. Years later, I was using her phone when I made an utterly chilling discovery.
The Truth Always Comes Out: Dark Family Secrets Exposed The Truth Always Comes Out: Dark Family Secrets Exposed
Factinate Featured Logo Featured Article
Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress
Factinate Featured Logo Featured Article
I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.
These People Got Revenge In The Most Ingenious Ways These People Got Revenge In The Most Ingenious Ways
Factinate Featured Logo Featured Article
Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.
Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife


Dear reader,

Want to tell us to write facts on a topic? We’re always looking for your input! Please reach out to us to let us know what you’re interested in reading. Your suggestions can be as general or specific as you like, from “Life” to “Compact Cars and Trucks” to “A Subspecies of Capybara Called Hydrochoerus Isthmius.” We’ll get our writers on it because we want to create articles on the topics you’re interested in. Please submit feedback to contribute@factinate.com. Thanks for your time!

Do you question the accuracy of a fact you just read? At Factinate, we’re dedicated to getting things right. Our credibility is the turbo-charged engine of our success. We want our readers to trust us. Our editors are instructed to fact check thoroughly, including finding at least three references for each fact. However, despite our best efforts, we sometimes miss the mark. When we do, we depend on our loyal, helpful readers to point out how we can do better. Please let us know if a fact we’ve published is inaccurate (or even if you just suspect it’s inaccurate) by reaching out to us at contribute@factinate.com. Thanks for your help!

Warmest regards,

The Factinate team