We’ve all been there - dates that turn out cringe, his teeth falling out while kissing, or banging heads during a first kiss. I want to hear your biggest embarrassment when it comes to love, romance, and dating.

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#1

There was four of us in high school, all friends, who all fancied the same girl. We had to talk it out over who would be the one to approach the girl.

None of us factored in the possibility that she might have her own opinion and fancy someone else entirely.

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Final score:
24points
Nathaniel (He/Him) Cis Het.
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I’mSoEmotional
I’mSoEmotional
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1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

As a girl in the 1970’s, this was always frustrating, because it felt like we had no choice in choosing who we wanted to go out with. Of course we could try to make it known, but boys weren’t great at picking up on subtle clues at that age.

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#2

I had a huge crush on a boy in school that almost every other girl also had a crush on. One day in class it was quite warm (there was no central air con) and I felt horrible. The bell rang and we filed out the door with my crush right in front of me. I tried to push past him but was too slow and I vomited all over the back of his shirt and jeans.
So he noticed me just not in the way I had hoped.

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16points
I’mSoEmotional
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#3

I have an extensive list of first and only first dates.
I blame it on nerves.
One date- While sitting in my dates brand new pick up truck and hearing him tell me all about it on our way out, I nervously stabbed my straw through the Styrofoam cup and I could feel all the bright red drink pouring out.
I held my legs clutched tight hoping to contain the staining substance from the new lovely seats and floorboard.
I was unsuccessful.
When we got to the restaurant, he could tell something was wrong...I stepped out to reveal the horror.
Never called me again.
Neither did the guy that I accidentally bumped with my head as he was leaning down to pickup my phone I had dropped.
He ended up with a black eye, and never called again.
And the small diner, where I was in the ladies room trying to spiff up with some lip gloss and re-clip my long hair up. I wanted to look nice while we sat across from each other. Then I dropped my oversized hair clip into the toliet and caused it to severely overflow - sending the employees running.
My date knew that I had just left the restroom and he wasn't buying that it was my hair clip that did the damage. I didn't even get to have dinner.
And the one date that I had to have perfect aim. On a brunch date, while going for the grapefruit, I managed to send a stream of raw juice right into my date's left eye. He was even wearing glasses! I could have never made that shot if I had been trying! I was so sorry, but I unfortunately snickered at the way he looked with his squinty eyes and mad face.
He couldnt see the funny side of the whole ridiculous thing.
I think somewhere there may be a blacklist with my name on it now. Possibly a small club of ex first date guys that are still trying to forget the experience with me.
I still like me. I just should come with a warning label.

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13points
kary On
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#4

The cringiest. I was so in awe that I'd finally got a date with my new girlfriend that I sat in a pub with a daft puppy dog expression, saying "I can't believe this is happening"

Amazingly we survived that terrible date and it didn't put her off. We were married 4 years later (I tend to think that the 4 years were her making sure I didn't do anything that sickly from thereon!)

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12points
Peej Maybe
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#5

I was dating this guy, and he was super clingy at all of the wrong times. Also, he was a huge pick-me "nice guy" type too. There were a lot of red flags. He'd show up at my job and try to hang out while I was working, and since it was a super informal and social job (a summer job), he could hang out with me when it wasn't busy, but when things got busy he would be super annoying when I was trying to help customers out. This one time I called him and told him not to show up at my job because my coworker (and close friend) had just gone through a breakup and I knew he would be clinging to me like a sock monkey and I didn't want my friend to feel bad. He hung up on me and showed up anyways. I refused to talk to him, I had politely asked him NOT TO SHOW UP and I was busy WORKING. He begged me to talk to him, while I was helping customers, and it was so embarrassing. He got upset and left. All of our "firsts" were ruined by him doing something like that and me getting mad. And when I finally ended things, he basically harassed me until I blew up on him. Now I'm a crazy b!tch. Lol I will never give that guy the time of day again.

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Bi the Way...
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#6

In college there was a girl I caught seeing me almost every day for several months, I approached her, as I was trying to start a conversation, she told me she had never seen me in her life.

I never recovered from that.

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Final score:
9points
Sihana Beluli
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#7

Well. My whole grade had gone for a feild trip and on the way back on the bus I was doing a wordsearch on the bus, and my crush came over and started helping me, and behind us my friends were making hearts with their hands and my crush's friend starts screaming "I SHIP YA'LL" to which my crush replied "Wtf no, have u seen the height difference?!"

He's 5 feet n im 5'4. Bro hasn't had a growth spurt in 3 years according to his friends. GrOw Tf Up B****

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Tanii
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#8

Online date, a friend's wife worked with him and while I'd initially said "No", I finally agreed. We were to meet for dinner at 8:00 pm. He was 20 minutes late. I was standing up to leave when a gentleman walks in, when he sees me he says, "Shelly?" When I looked up at him I had no idea who he was. Then he says his name! The picture on his profile must been from 25 years ago! I'm there, so we get seated. As we're sitting there he begins the conversation by saying the following in a VALLEY GIRL ACCENT "Oh my GAWD, you look just like your picture.". I know I'm in for a long night. I flag the waitress and ask for a glass of wine (I normally don't drink on first dates/meet ups). Suddenly he's on the phone and say's, "Yah, she's right here!" and hands me his phone. I'm absolutely clueless, then I hear a young girl say, "I'm so & so's daughter. I want to know what your intentions are for my dad!". I'm gobsmacked, I've know idea why he did this. I mumble some platitudes & hand the phone back. Now we're ordering, I've had gastric bypass, so I'm not a big eater. I'm torn between halibut and prime rib. Before I could say anything to the waitress he jumps in and orders BOTH halibut and prime rib. I immediately tell him I won't be able to eat all of it. "Take a doggy bag home."
The whole night was filled with him talking like he was a Valley Girl. We're done and he's walking me out to my vehicle, when he says, "I really thought you'd drive a truck since you snow machine. But your Neon is cute!" How in the he!! does he know what I drive? I was there 20 minutes waiting for him. Thoroughly freaked out I say, "You know, I'm going to head back in to use the ladies room." Before he could say anything I beat a hasty retreat inside, where I waited for an hour before I had an acquaintance escort me back out. He called repeatedly, his FIVE kids called me (his profile said he had 3). I finally sent him ANOTHER email where I unequivocally stated I wasn't interested in pursuing ANY type of relationship with him.

My online dating period are somewhat a study of what men shouldn't do when they post a profile AND decide who they're going to reach out to! Especially if you DON'T have any of the traits she's looking for in a partner!

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Final score:
7points
Shelly Graham
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#9

Went on a first date...i live in a very small town...an everybody, knows everybody kind of town. He lives in a much larger town approx 1.5 hours away.

He drove to my town to take me to dinner at, frankly, the only "fancy" restaurant in town.

He was such a perfect gentleman, so amazing, doing all of the awesome things that first dates do...so we went to the restaurant. He had made a reservation for the nicer Steak House section of the restaurant...as we were walking through the restaurant to our table...we had to pass through the cafe area, the bar area...all tables that overlooked the corridor where you walk to the fancy steakhouse...as my date and I, ON OUR FIRST DATE, HOLY SH*T!!, walk through said corridor...I hear "Oh my gosh, Honey! I didn't know you were going out tonight!" My Dad and Stepmom, who are sitting at one of those tables, flagged us over. Now, please note, I truly had No idea they were going to be there, I was praying the guy wouldn't think I was some psycho chick that tricked him into meeting my parents on the first date. Stepmom was her awesome self - just talking me up. like he should understand that I was all that and a bag of chips (I'm not), Dad shakes hands, I spend the rest of the date apologizing and trying to make him believe I didn't do that on purpose... that was 5 years ago- he decided I was worth taking a chance on...he still thinks my family is a little nuts here and then...

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Final score:
7points
Jim's Panda
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#10

In like 4th or 5th grade I think, this kid who I MAJORLY thought I loved, asked if I liked him..

I said, "No" and ran away. 3 years later come to the realization i'm asexual 😅

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6points
Crow of Approval
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#11

I asked my bff out not know he's gay

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6points
Animal lover xoxo
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#12

Mine was a week ago I asked my crushed to a dance in front of everyone and he rejected me I was crying my eyes out the whole night.

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6points
Jasmine DevilBiss
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#13

Mine is more weird I guess, but here goes. I'm at my new boyfriend's house, it's a little awkward, but whatever. We're holding hands and watching a movie. Near the end of the movie my anxiety kicks in and starts taking over again. I had to text my mom and leave an hour early, during which I was trying not to cry. Once I got home, I heard that my boyfriend was scared that I changed my mind about liking him. I texted him an apology and assured him that I still loved him. We're still together and I'm working on not letting anxiety take over.

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5points
ThatOneQuietKid
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Milky Way Cookie
Milky Way Cookie
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'm sure he understands, anxiety sucks, we should make a 100% permanent cure for any unnecessary illnesses all together!

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#14

In 7th I had a crush on a dude who I didn’t realize was a major conservative republican Trump supporter.

We would’ve clashed a LOT.

that was a low point.

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tragicaltales
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#15

A long time ago in grade school (I don't remember what grade) we were all in the gymnasium and there was a stage that was about 4 ft high. I was on the stage area messing around when I seen my crush. Well she seen me too and waved to me and I waved back while walking towards her. Apparently I was so enthralled by this that I didn't notice the stage had ended and walk right off the stage and smashed my face on the ground knocking me unconscious for a bit. When I came to everybody had surrounded me including my crush. Still haunts me to this day. Probably 30+ years

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4points
PhattyMcgee (OB/CD)
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#16

Not as much mine as my husband's. Our first official date was to be New Year's Eve when he got back to town from a wedding 3 hours away. His car broke down, and this was before cell phones were common. By the time he got to a phone, it was well past midnight. Instead of calling, he got what he needed to fix the car and then drove straight to my house because the only proper apology was going to be in person at that point. I forgave him, and in June we'll have been married 30 years.

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ThisIsMe
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#17

Crush on this awesome girl. Smart, pretty, etc. One day (or more correctly, one evening) she says to me "rub my back". I do it. She then says "I'm horny". I was like 25. I ran. WTAF.

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censorshipsucks
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#18

Not being able to get any girls and my friend who is a girl(Trans now at the time of this)saying “I got more b*tches than you”. I usually end up responding with “Work is more important.” Usually shuts them up.

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Average Chicago sports fan
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Average Chicago Sports fan (Submission author)
Average Chicago Sports fan
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

In general I’m hopeless when it comes to romance and love. Also I don’t find it that important right now necessarily because achieving my goals is more important.

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#19

I would like to tell, but it would all be censored.

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Elizabeth VanDyke
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#20

Not really mine- but it happened to me. In 7th grade, I was at the “snowball dance.” One of my friends at the time, let’s call him Tom. Me and Tom were best friends since 3rd grade. He had a crush on for YEARS. And at the dance, he was wearing a tuxedo, had his hair all “fancy” and walked up to me INFRONT of all of my/his friends and said: “[My name] I have loved you since I set my eyes on you… will you be my girlfriend?..” I said no, and he started crying, and Tom ran off to the bathroom. I felt so many different levels of cringe, to this day. I felt so bad for him!

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AwfullyWaffley
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#21

In 6th grade, I sent a letter to my crush at the time, saying she was good looking, etc. and then EVERY DAY from then on, the whole class would fight for whatever reason

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Andrei Marentette
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#22

Went on a first date...i live in a very small town...an everybody, knows everybody kind of town. He lives in a much larger town approx 1.5 hours away. He drove to my town to take me to dinner at, frankly, the only "fancy" restaurant in town. He was such a perfect gentleman, so amazing, doing all of the awesome things that first dates do...so we went to the restaurant. He had made a reservation for the nicer Steak House section of the restaurant...as we were walking through the restaurant to our table...we had to pass through the cafe area, the bar area...all tables that overlooked the corridor where you walk to the fancy steakhouse...as my date and I, ON OUR FIRST DATE, HOLY SH*T!!, walk through said corridor...I hear "Oh my gosh, Honey! I didn't know you were going out tonight!" My Dad and Stepmom, who are sitting at one of those tables, flagged us over. Now, please note, I truly had No idea they were going to be there, I was praying the guy wouldn't think I was some psycho chick that tricked him into meeting my parents on the first date. Stepmom was her awesome self - just talking me up. like he should understand that I was all that and a bag of chips (I'm not), Dad shakes hands, I spend the rest of the date apologizing and trying to make him believe I didn't do that on purpose... that was 5 years ago- he decided I was worth taking a chance on...he still thinks my family is a little nuts here and then...

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0points
Jim's Panda
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