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These cringy AF first relationship stories will make you gag

Do you remember your first high school relationship? Whether it lasted three hours or three years, you probably have some really cute memories – like swapping chewing gum behind your locker doors – but also some pretty cringey ones that you try really hard not to remember, let alone tell anyone. But since Reddit is kind of just a black hole of anonymous confessions, one user’s request to hear cringe first relationship stories really delivered the goods. Here are some of our favourites:


gag relationship stories


He tried to save a life


“High school girlfriend and I used to make out on her bed with the door locked. Heavy kissing and at some point, she says cut that out, your breath stinks. Start kissing her neck and she slowly wraps her leg around my thigh. Couple minutes later started breathing heavily. Her legs tighten around my thigh. After that, she suddenly goes rigid, eyes roll up till I see whites, rapid breathing, exhaling heavily. I panic; she’s choking. I should give her CPR, but she said no kissing her mouth. So, I close my lips around her nose and blow it like a trumpet.


TLDR: didn’t realise GF was having an orgasm, thought she was dying, tried to save her by blowing straight into her nose. I am a moron.”


Strawberry kisses


“I was young and had my first boyfriend. We were ‘experimenting’ sexually, and I really wanted him to think my p**** tasted nice, so I would literally rub strawberry flavoured fucking lip gloss in my vagina. There’s no way he didn’t know. I thought it was such a genius idea that I had to share it with my fellow women, so I wrote it down and passed a note in class to one of my friends. It dropped on the floor and all of the boys read it. Strawberry lips was my new name and I cried for a week.”


Back from the dead


(We) started dating three months before sophomore year ended. Once summer started, I completely ghosted her. Skip to first week of junior year, I thought we were still together. You can imagine how she reacted when I approached her for a kiss. The shame is still real to this day.”


Is honesty always the best policy?


“Told my first real GF that I’m glad she wasn’t the most beautiful girl in the world, so I didn’t have to worry about every guy trying to steal her.”


"you're ugly" relationship story


A family affair


“My first kiss was in the movies at The Bounty Hunter. It was interesting because I also got my first blow job a few minutes later in the same spot. I remember 4 things:

  • My parents and her parents were two rows in front of us
  • The looks of disgust on the old couple’s faces four seats down
  • She swallowed and it was way too much sensation for 16-year-old me
  • Gerard Butler was in it.”




“I was 17. We had just had a fight. I drove to his house and blasted “Scars” by Papa Roach from my car and just stood awkwardly at the end of the drive way waiting for him to come out. I really wish this weren’t true.”


Too soon?


“We were in seventh grade and had been dating for maybe two weeks. I printed a marriage certificate and showed it to her the first time she came over to my house. She called her mom and asked to go home immediately.”


Too soon relationship


Can’t blame a guy for trying


“She thought we would be better off just being friends, so I decided that I needed to do some big grand gesture to prove my love – it always worked in the movies, so what could go wrong?


I practiced singing the song for weeks on my ukulele and figured that I would wait until after her softball practice was done and surprise her. I sang “You’re Beautiful” by James Blunt. I wasn’t a terrible singer, but I wasn’t good. We were not friends after that.”


And they say chivalry is dead


“She showed me a topless pic and I was too embarrassed to look at it.”


Everyone has awkward first relationship stories to share and laugh at – but we really hope you can’t relate too hard to any of these. Do you have a cringe-worthy relationship story you’d like to share? Drop it in the comments below!


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