Recently, a Redditor asked users “What is the most embarrassing thing someone has done, who was interested in you romantically?” Here are the users’ best and most cringey submissions.
[Source can be found at the end of the article]
A girl I knew in middle school stabbed two people with a pencil for talking about me behind my back. She was upset when I didn’t thank her.
This girl in college who was a sort of friend once drunkenly called me and left me a three-minute message confessing her crush on me. Then she did it again, but on the 2nd call, she tripped on something and started crying and eventually the recording was too long, so it stopped.
I was her first kiss. She was standing 5 feet away from me. She puckered her lips like a duck, closed her eyes and blindly walked 5 feet to kiss me. I could have met her half way….I didn’t.
I was dating this girl for like 1 month. We had a conversation about how much we loved ‘The Lion King’. It was playing in theaters at the time – Disney rereleased it in 3D (this is like 3 years ago). So we went to see it and had a great time. After the movie we bonded in our love for the character Scar.
The next weekend we made plans to hang out again. We were sitting in my basement and she told me she had a surprise for me. She sat on my lap with her back facing me and told me to lift up her shirt. I did, only to find that she went and got a fairly large tattoo of Scar from The Lion King. It was hideous. I was very freaked out. I knew it would make it harder to break up with her.
In high school a friend of a friend made me a build-a-bear that said ” [my name] I love you, will you go out with me?” And presented it in front of our mutual friend groups. I was so shocked that I couldn’t find the words to reply, so after a solid minute of stunned silence he trashed the bear, fled the school, and didn’t come back that day— still feel bad about it 10 years later.
A girl kept some of my hair in a box with photographs and illustrations of me about 2 weeks into our relationship.
My horror must have been embarrassing for her.
That was also the final week of our relationship.
It was our second time hanging out. His phone had died while on the way to my house and he had to navigate on his own. I didn’t know this and had assumed he bailed on me. I was furious. He ended up getting lost but knew there was a Walgreens near my place. He stopped by it and borrowed the store phone to call me to drive down and guide him up to my place. I showed up at the store and there he was, super embarrassed looking, holding a bouquet of flowers. I felt so bad for him, but at least he didn’t bail and tried to make things work.
My first serious boyfriend and I decided to lose our virginities to each other, he had this thing if he got extremely nervous or anxious he’d throw up. Well things start heating up and the first time he puts it in all he said was “Oh my god, it’s tight and warm. Cue the fried Oreos and milk all over my face, hair, and chest. Unfortunately for me he had just come back from a football game with a FINE menu…
I was walking to class when I heard some loud group laughter behind me. I had my headphones in and there were way too many people for me to want to wander back and find out, so I kept going to class.
I started dating a girl soon after that, and found out a few weeks later that she had dramatically fallen and taken someone else out while trying to catch up to me in the hallway. We had just started talking, and she had worn a cute dress and some heels to get a little bit of extra interest from me. She wasn’t the type to wear heels often, so she took a bit of a tumble while trying to speed walk to get to me. Adorable thing she was…
There was a girl I used to know who always wanted to start a webcam chat. I didn’t have a webcam, so she would just video call me so I could watch hers, except she wasn’t really doing anything. It was just a stream of part of her face as she typed. Also, she’d get really offended if she video called me and I didn’t accept, so I would usually just accept, minimize the window, and go on with whatever I was doing.
I went out with a guy who had terribly horrible gas. It started at the bar and pretty much didn’t stop all night.
I’m not unreasonable, we’d gone out before and it wasn’t an issue. But the next time we hung out I went to his place. It was a sty. And he was grilling pork on a grill, and persistently wanting to consider it done because it was browned on the outside. I kept cutting the insides open, where the meat was still raw, explaining pork isn’t one of those meats you can eat half cooked. Probably explained why his intestines hated him so much.
And yeah. He was gassy that day too. Sorry, I tried.
This guy I was friends with confessed his love to me while at a Taco Bell. We worked together and I was his superior and not at all interested in a relationship. I told him no, first of all because I was his boss, and second because I wasn’t interested in him romantically. He begged me for 15 minutes and insisted he would quit for me. I told him he was stupid to even consider that and refused to continue the conversation.
After that, our friendship went downhill and we ended up not talking at all. Our work relationship suffered too, because he thought he was somehow better than me, or was insulted that I turned him down.
It was horribly cringy for him, especially since his entire interest in me (as friends) was based around the outcome of us eventually dating.
When I was in third grade, a boy I was kind to got the wrong idea. Not sure what was going on with him personally but he had special classes/ sometimes a teachers aid so potentially a little off. One day in the cafeteria he screamed “(my name), I love you!” At peak volume. The entire elementary cafe went silent as I slumped back to my seat. I tried to avoid him after that because his indoor volume was that of the park ranger Carl on Parks and Rec.
We still don’t talk sometimes.
When I finished my first date with my now wife, she was acting a bit awkward, well, more so than is usual for her. She was smiling at me, touching my arm, but wouldn’t do anything unless I brought it up because she was so shy. Once I finished walking her back to her building, I asked “Do you mind if I kiss you?”
To which she said something between “Yes, please” and “uh-huh”, kinda sounded like “Yuh hease”. Then, she went on her toes, was still too short, and kind of pressed her lips against my chin before turning beet red and started walking into her dorm.
Took me a second to process what happened before I started laughing, asked her to wait, and then leaned over a bit to give her an actual kiss. Now she just throws a pillow at me whenever I bring it up at this point.
I dated the most egocentric dude in all of New York. His dad is a famous musician, so he’s lived a life of yes-men surrounding him and whatever toys he’d like… this has resulted in him believing without a shadow of a doubt that he is super talented at everything. Spoiler: he’s not.
He knew I wasn’t interested in him. I told him gently at first, then firmly, then flat out. I’m hanging out with my friends one night and he FaceTimes me… he had somehow clipped his phone onto his guitar really close to his face, and was live streaming his band practice at me singing directly into the guitar camera. It was a really bad angle, the music sounded terrible, his expression was just SO into himself, and I ended up ending the call after my friends got a good laugh because I felt such intense second-hand embarrassment.
Back in high school I was partnered with this guy for a physics project. Really great guy, enjoyed his company a lot but wasn’t interested in him romantically and he knew that.
We had to build a bridge out of some very lightweight wood that we had designed to be able to hold a certain amount or weight or something (can’t quite remember the specifics of the project) and at the end we decided to cure the glue we’d used. He said he had it covered so I stayed in the other room texting or something while he put it in the oven.
20 minutes later the kitchen was smoking. Turns out he had put the bridge in with some chicken nuggets he was making us as a snack so I would stay longer and just hang out, but he completely forgot about the bridge. The wood eventually caught on fire and we had to start the project from scratch. He was mortified. Best chicken nuggets I’ve ever had, though.
I worked on the maintenance crew at a summer camp the year after I graduated high school. One of the female counselors took a shine to me early on, which led to two good stories.
First, I was working some particularly dirty job on my birthday (during a week of junior high campers), so I went into the bathroom to clean up before lunch. I took my shirt off to make the process easier, and walked out of the bathroom with it in my hand, about to put it on, only to be greeted with a thunderous round of “Happy Birthday” from the whole camp, which almost covered up the squealing and giggling from the girls in this particular counselor’s cabin. Looked over to see her blushing bright red in full view of everyone, surrounded by giggling twelve year old girls.
Later in the summer, she basically jumped on me and kissed me mid conversation with no warning, after we had talked about holding off on anything until we were at college together. I had no idea what to do, so I just kinda sat there. She ended up crying and mildly panicking about it.
It’ll be five years of us dating at the beginning of August, I’m moving to a tiny town to work at the same place as her in September. I guess it turned out okay.
There was a guy in my grade 9 music class. He played tuba and I played clarinet, so we never really talked until the last few weeks of the semester. We had held conversations on a total of 2 days before I received a 2 page Facebook message from him talking about how much he liked me, how often girls rejected him, and how he was about to drink cold medicine to get high. I still have the screenshots somewhere. He also wrote a song about me, I never got to see it but a mutual friend said he showed her some of it and it was pretty brutal. Somehow he calmed down by the time we were in grade 11 Intro to Psych class together and we ended up pretty good friends. He also started a relationship around that time which made me feel a lot better about the situation, although he did propose a threesome between him, his fiancee and me in grade 12 (yes he proposed while he was 17 in high school and she was a freshman at college… when he told me I was about to give him an earful until he added that they were going to wait a few years before the actual wedding). It’s been a bit of a wild ride knowing him, but all in all it worked out alright.
I was at Electric Forest (a music festival in Rothbury, Michigan) in 2015.
I’m standing off to the side by the vendors at the Tripolee Stage (across from where the ferris wheel/entrance is located) watching one of the closing DJ performances by this duo Art Department. Decided to grab some food before heading back to camp for the night so I’m standing out from the crowd, eyes bouncing back and forth between the onstage act and mass of people.
Suddenly this gorgeous woman, sprints out from the front row of the crowd along the gate toward the tree line. As soon as she hits open space she vomits quite an impressive distance.
She looks up, wiping the corners of her mouth. We lock eyes. She giggles, bashfully smiles, and sprints/dances her way back into the crowd. I immediately fall in love.
It was the most poetic puke I have ever witnessed; one that was likely not induced by overconsumption but rather from pouring every ounce of physical energy in her tiny frame into dancing.
Still hoping that recounting this tale will one day lead me back to my projectile princess.
In my freshman year of high school, a girl who I had talked to maybe 3 or 4 times, in passing conversation, interrupted my first hour class to give me a bouquet of slightly dead white roses along with a note. The teacher had no idea what to do, and the girl just stood there in silence waiting for me to read the note. Eventually, with the whole class staring at me in silence, I said “I’m gonna read it later, if that’s okay?”
Immediately her face fell and she left the room crying. I apologized to the teacher for the interruption and explained had I had no idea what had happened. The note professed deep love for me, her soulmate. I never heard from her again – she dropped out soon after to become an influencer for a local venue, I believe.
One time a guy was trying to be cute and zip up my coat for me. He started to raise the zipper, but it got stuck near my cleavage, so he pulled with force. Unfortunately, his hand slipped off the zipper and he gave me an uppercut instead.
A different guy took me out for our first date to a hiking trail because he was working on a photography project. I followed him around and had a lot of fun. He ended up jumping over this little creek to get a picture of a tree hanging over a river. I knew I couldn’t make the jump without falling in, so I let my shoes get wet instead. He began teasing me about it as he stood on the log of the tree over the water. He gets what I assume was a great picture and then turns around to step back onto the bank. He ends up slipping into the water up to his knees. When he steps forward, he must have stepped into a hole under the water, because now he is up to his chest in the water. Luckily, this was before everyone had cell phones, and he kept his nice camera above his head, so only his clothes were soaked. I almost peed my pants laughing.
I was dating this guy for 6 months when I was 18; he was 29. I mention this because I kind of feel like he should’ve been the responsible one.
Anyway, things start to inevitably go south because I’m much younger, and I’m not on the same page as him. He wanted us to get a flat together and live together and get dogs… and I just wasn’t into it at that point in my life. I just wanted to go out and have fun together.
He started worrying me when he hinted that he was going to surprise me with a pair of puppies, and what names would I like to call them because how cute would it be if they had little collars on with names I’d picked out for my ‘dream dogs’. I should have ended it there, but like I said. 18. Read stupid. Ostrich level stupid.
A few weeks later, he took me out to dinner and said he had a surprise for me. When I asked him what it was, he unbuttoned his shirt a few buttons, slipped it off his shoulders and turned around to reveal a HUGE tattoo sprawling across his upper back, of my name. It was literally shoulder to shoulder. My name is quite unusual and is 9 letters long. The dot on the ‘i’ in the middle of my name was a star on the back of his neck, it was that big. Additionally; it was red at the top, fading to skin colour, then through to blue at the bottom. An ombr of disappointment. I don’t think I can accurately put across what a monstrosity this thing was.
I was totally gobsmacked. It sort of felt like a violation and I can’t describe how or why. It just did. Needless to say, I broke up with him the next day. For all I know; he’s still walking about with that thing on his back, because it would be literally impossible to cover up.
So when I was like 14, I used to hang out with this guy in my hometown who was really into anime, specifically Bleach. All he wanted to do was talk about Bleach, online role play in the Bleach universe, etc. And he wanted me to participate. For some reason I put up with this even though I had no idea what Bleach even was.
So I guess because I was female and paying attention to him and we were 14, he developed a crush on me. Here’s how he decided to tell me:
We are chatting on AOL Instant Messenger one night when he suddenly confides in me that he has an alternate personality. It is an evil personality that wants to destroy all humanity. It is probably directly inspired by something from an anime.
I ask if I can talk to this alternate personality. He agrees to “let him out,” and then starts typing in complete sentences with capitalization and punctuation to indicate that the alternate personality is really sinister and smart. But apparently not smart enough to realize it could go kill some humans instead of chatting with a middle schooler on AIM.
The alternate personality informs that it really wants to kill me, because I am a human and it wants to kill all humans. In fact, it would have already killed me, if my friend hadn’t stopped it through sheer force of will. My hero of a friend had been bravely holding it in check, all this time. “You’re lucky he likes you,” the evil personality tells me.
I ask to talk to my friend again, and he drops the act with plenty of dramatics about how traumatic it was to let the evil personality out. After a minute or two, when it’s apparent that I’m not going to acknowledge his pseudo-confession (I was naively hoping he just meant “like as a friend”), he doubles down. “I can’t believe he told you…I didn’t want you to find out this way…”
So yeah, instead of just telling me he liked me, this dude made up a fake evil split personality to confess on his behalf in between threats to my life. It is, to this day, the cringiest thing I have ever directly witnessed. But I can’t really judge, because I was also 14 and I was just as terrible in my own special way. Weren’t we all?
When I was 13 a girl had a crush on me. Did I find out because she told me, or because of a friend? Nope. I found out because she made a Powerpoint slideshow about us dating, marrying, and growing old together.
The first slide was about how we met in her imagination, and went on to show stock photos of couples. There was a slide of us on our first date, one of us getting married, one of us having kids together, ect. This was a full one slide show with pictures and cheesy word art. I don’t remember how long it was, but I think about 10 slides. I clearly recall the last slide being an old couple and it said something about us growing old together and bring in love the rest of our lives.
As you can imagine I was not the first to see it. Many other people had seen it and it had been circulating for a few days before a couple of my friends pulled me into a classroom and showed me one day, laughing the entire time like good friends do. From then on anytime I was around her it was awkward. I didn’t have feelings for her before the Powerpoint, and afterwards was creeped out and had a bit of an aversion to her.
So, there was this girl that I was just not interested in romantically. At all. But she would often find her way into my circle of friends when we were all hanging out. We weren’t unfriendly to her, but she was also a girl that took any sort of joking or compliment or just saying “hi” to mean flirting and would not take a hint. She would awkwardly text and IM me, like “Hey, you there?” “Yes” “Okay, just checking…” and that was it. So one night, she is hanging out with my group of friends. She looks at me and says, “This is weird, but I want to touch your beard.” I gave that WHAT?!? look and with a disinterested tone said, “fine.” She then debated for several seconds out loud if she should touch it. When I said, “just do it. you’re making it awkward,” she finally touches my beard. And she says, “This is the single greatest experience of my life.”
The daughter of my babysitter took me down to the basement where we were alone and cornered me. She then asked me if I loved her. It really threw me off and I didn’t answer her right away so she asked me again. And I realized she was really being serious and I just kind of stuttered. And she just asked again and started crying and she kept saying over and over ” Do you love me”, and I was young and confused and just said yes. She gasped with relief, wiped her tears, smiled and hugged me and just then went back to being normal like that never happened.
Well, I wasn’t sure if she was romantically interested. This was my senior year of high school (12th year), fairly early in the semester. And I was hanging out with an acquainted group of people as I was waiting for my ride to go home. While we were standing around, I had a lollipop in my mouth and conversing with the group. All of a sudden one of the girls from the group stood very close to me, less than a foot away. She proceeds to rip the lollipop out of my mouth along with chipping a tooth. She puts the lollipop in her mouth and leaves. And I mean she power walks out. I still saw her around school, but she avoided me.
I guess she thought it’d be cute to do that, but I sure didn’t. I also thought it was extremely weird to take a lollipop from a stranger’s mouth and then putting it into their mouth. She messed up my tooth!