15+ Reddit Users Reveal Their Cringey First Relationships

Diply 19 Oct 2018

You know how you always have positive memories about your first relationships, and you're never embarrassed at all to think about them?

Nah, I'm just kidding. That just doesn't happen. For most of us, first relationships are about learning, and fumbling, and discovering what we like, and more often than not, what we don't like.

And, even better, those learning experiences can turn into stories, like the ones that Reddit user offendedbywords invited people to share when they asked Reddit "What was the cringiest thing you did in your first relationship?"

1. "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." —ToastBudder

Getty Images | Chip Simons

It's so awkward when you forget to break up with someone, isn't it? Like, I'm legally married, but I'm pretty sure I still have a girlfriend from high school I'm technically still dating. If you're out there...I'm sorry, I just don't think it's going to work out.

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2. "She started to ignore me at school [...] I called her house like 6 or 7 times one afternoon after school until her mom picked up [...] I hear in the background 'Alexa why aren't you answering the phone??' To which she responds 'Because he's weird and he just keeps calling!!' I hung up the phone and went to my room. I carved her name in my wall with a pen." —ThePathGuy

Getty Images | byllwill

You know you've reached peak emo status when you're not just writing on the wall with a pen. You're carving into the wall with the pen.

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3. "We wound up running out of seats, so for some reason, my mom decides to let me sit in the trunk of the van with my boyfriend, what could go wrong [...] we wound up making out in the trunk for the entire drive. What never crossed either of our hormone-addled brains was that ALL OF MY FRIENDS AND MY MOM COULD HEAR US GROSSLY MAKING OUT." —DeadlyKitten00

Getty Images | Constantinis

I can absolutely hear this story in my head right now. That might be because my coworker is eating lunch and he chews with his mouth open, but I feel like it sounds pretty the same.

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4. "Was walking her home anticipating kissing her for the first time at her doorstep and kept licking my lips because I didn't want to kiss her with a dry mouth. Halfway to her house she looks at me and says 'stop doing that.'" —SuzukiiLock

Getty Images | RyanJLane

There's a certain amount of chill that you don't learn until you're much older. Unfortunately, you don't know what you don't know until someone points out that you don't know it, y'know?

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5. "After I saw Eric propose to Donna on That '70s Show, I went out and got a 25¢ ring from the local Pizza Hut and proposed. At school. In front of everyone. I was 16." —TheNoslo721

YouTube | randomchannel137

Considering how much we all watched That 70's Show, it's weird that we don't talk about it more, isn't it? Then again, if you're living your life to be more like Eric Foreman, you probably peaked a while ago.

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6. "We took a 'break' and I posted a video to Creep by Radiohead with the caption 'For that special someone.' Ugh. I almost cringed off my chair writing this." —dmey91


I mean, what're songs for, if not to weirdly point in the direction of our failed relationships and then wonder why that doesn't fix everything?

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7. "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 driveway waiting for him to come out. I really wish this weren’t true." —mastercait

Getty Images | PYMCA

It takes a whole new level of angst to try and weaponize that sad-boy music energy and actually bring it to someone's driveway. You're not John Cusack, this isn't going to work.

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8. "Never turned to a relationship, but the way I wanted to declare my love to my crush was as follows: scream 'I love you, [crush’s name]' during math class." —--who

Getty Images | Wealan Pollard

Honestly, this probably wasn't the best picture to go with this caption, but look how excited that kid is to tell us something. He absolutely just found a dead frog or something in the playground.

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9. "Let my mom purchase custom matching airbrushed shirts of two people kissing, with my girlfriend and my name on them." —ArpeggiatedAnt

Reddit | Chumpfirce1

It's a pretty good sign that if your mom is the one leading the romance in your relationship, then you probably aren't ready for a relationship.

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10. "After the first date of going to the movies (I never put my arm around her because I was too scared), we sat in my driveway, and she didn’t say good night because she was waiting for me to kiss her. I did nothing, so she finally kissed me. In defense mode, I lick my lips all the way around with my tongue like Scooby Doo does with the cotton candy in the theme song intro. I even did the 'reeheeheeheehee.' Kill me" —BlueSkyPeriwinkleEye


This just got worse and worse as time went on. Like, I almost sympathized until that last sentence, and now I just kind of want to walk away and never come back.

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11. "She showed me a topless pic and I was too embarrassed to look at it." —Darkblitz9

Getty Images | vgajic

Except, I get the feeling that this actually happened in person. Which is a HUGE rejection to do to someone.

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12. "I got us matching dog tags with our anniversary on it after dating for around 6 months and would secretly get very sad when he wouldn't wear his." —Reddit User

Getty Images | Doug Menuez / Forrester Images

Ah yes, who can forget how important each individual month was when you first started dating? Omg, it's been four months, we'd better start picking out mortgage brokers.

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13. "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." —Reddit User

Getty | Nerida McMurray Photography

I don't think anyone can blame this girl for executing her exit strategy immediately. It was the right call, and everyone learned something.

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14. "I was so nervous on the way home. Being 14, his dad drove us to my house to drop me off. I leaned over to kiss him on the cheek. A quick peck and then I threw up his mom's fajitas all over myself." —Reddit User


Well, at least the story ended with the word "myself" instead of "him." Not that it's that much better, but it's at least a little bit better.

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15. "Well she said that 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." —mdicke3


If you don't think that I've at some point sung that song to try to impress a girl, you really don't know me very well. There's no reason that you should, but this kind of behavior is basically peak Dylan.

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16. "First real girlfriend in highschool, we used to talk over the voice calls on MSN messenger late at night. She wanted to just hear my voice, and I very quickly ran out of things to say, so she said I should just read whatever book I had around. She spent the next 30 minutes listening to my 'Your new Gateway Computer and how to use it!' booklet." —sixesand7s

Getty Images | Caiaimage/Agnieszka Olek

Honestly, I just wanted to end this one on something that's kind of sweet. I hope you all kind find yourselves a Gateway computer manual-reading kind of love.

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