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Top 10 Cring, Worthy Experiences People, Have Experienced In Their Frist Relationships

People often make mistakes in their first relationships that can be very cringe-worthy, but you have to have experiences to learn from them! Many people get to experience their first relationships in their early and pre-teen years or a little later. But no matter what, we have all had some moments we think about now where we think, “WOW! What was I thinking!?” Here are some cringe-worthy first relationship things some people have done. 

Abandon Ship

Woman wearing a green dress looking confused
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One Redditor replied, “This was with A girl I dated in high school.. my dad was getting drunk at a block party, so I got the idea to take his ski-boat and go for a romantic boat ride. So we park in the middle of the lake and start making out and stuff. We notice our feet getting wet. The boat was SINKING.”


Image credit:Depositphotos Alex_F .

A user commented, “Started dating three months before sophomore year ended. Once summer started, I completely ghosted her. Skip to the 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.”

Another user added, “I did the opposite of this! This guy asked me out during summer, and I said yes, so we just texted every day because we didn’t have the chance to meet up, and then I ignored him at school and dumped him. I wasn’t very nice.”

Not Beautiful

break up. Woman looking away sitting on the bed while the man sits behind her looking at her. They both look upset and angry
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A very cringy comment said, “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.”

Romantic Letters

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One Redditor replied, “The letters I’ve wrote… Oh, those letters.. 15-year-old me thought he was deep and romantic. He wasn’t! I hope they don’t exist anymore.”

A  second Redditor added, “In the 4th grade, I wrote anonymous love letters to a boy I liked and left them on his desk. I saw that he had thrown them away, so I started writing my name on them. He still threw them in the trash.”

Constant Phone Calls

Woman looking surprised with arms out to the side in question
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One comment was, “She started to ignore me at school (this was like maybe one or two weeks after we started dating). I called her house 6 or 7 times one afternoon after school until her mom picked up, who was basically furious because I had been calling. I explained to her that Alexa was ignoring my calls. 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 on my wall with a pen. I still cringe about it to this day.”

Lip Licking

Woman looking serious pointing at the screen as if she was asking us
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One weird comment was, “I 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 said, “Stop doing that.” I realized I probably looked really creepy.”

Another comment added, “My first kiss, I had a bunch of dead skin on my lips, so I tried to discreetly bite it off while we walked. She was doing the same thing, though lol. Winters in Michigan make lips chapped AF.”


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A Redditor wrote, “Broke up with her because my best friend told me to, we were perfectly fine together, but I guess I kinda worshiped the guy and his advice. He later tried asking her out when we split. We were all 14-15.”

Another Redditor responded, “Same story, first (or second?) ever girlfriend. Best friend said she’s ugly, so I broke up after two days. I think that I was 15… She was perfectly cute! And my “best” friend was just jealous, and I was a moron.”

Missed Opportunities

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Image credit: Depositphotos AsierRomeroCarballo..

A user commented, “Declined to stay the night because I was, and I quote, wearing a skirt and didn’t want it to ride up while I was sleeping.”

Another user replied, “Heh, a girl in my neighborhood once greeted me on her balcony wearing nothing but a towel, asking me to come up so she could show me something. Told her I couldn’t because it was late and I had homework. F**k’s sake.”


Woman holding her head
Image credit: Depositphotos piotr_marcinski.

One Redditor added, “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.”

A second Redditor wrote, “This happened to me in high school. My then-boyfriend and I had gotten into an argument the day before, so the next day at lunch, he proposed to me in front of the entire school. Didn’t even have the decency to get a ring, though.”

Butt Kicking

Fight Rules two men fighting
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A sad comment was, “Tried to defend her honor. I got the **** kicked out of me by 3 guys. I earned cred for taking a beating, but she thought we should just be friends after witnessing that.”

Another comment was, “My first GF I had in high school broke up with me after I got jumped and broke my jaw. God damn, I hate that b**ch. She didn’t even ask if I was ok.”

Video Break Ups

Woman shocked
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A Redditor added, “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.”

A second Redditor replied, “I had a similar incident, but the ex was the one who posted the video. To “Black Dahlia” by Hollywood Undead. I hope he remembers and cringes into the sunset every time he does.”

Musical Break Ups

Woman crying into her hands
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A user replied, “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.”

Another user commented, “This sounds like something I would have done. Add in some rain and mascara running down my face, and I threw myself in a puddle in front of him after we broke up. I have repressed that memory for 16 years until now.”

“I Love You.”

Woman wearing red lipstick looking to the side surprised
Image credit: Depositphotos deagreez1.

A popular comment was, “Told her I loved her within the first 24 hrs at the school parking lot.”

Another cringy comment read, “My first boyfriend said I love you(through text) within minutes of dating. I said, “umm okay.” And he said. “Aren’t you going to say it back?” As any middle schooler would do in their first relationship, I reluctantly said it back.”

Sexy Pictures

Butt woman on the beach in a yellow bikini faceing the ocean with her arms over head
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One Redditor added, “She showed me a topless pic, and I was too embarrassed to look at it.”

Hit and Run

Road Trips friends in a truck on a roadtrip
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A funny comment was, “I hit my girlfriend with my car. It was a complete accident. We are still friends, and it is a story that still comes up in conversation every now and then.”

Dog Tags

Discuss and Express Emotions couple talking and looking concerned.
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One person commented, “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.”

Another person added, “Guilty of this too. After we broke up, he posted a video on Facebook of his friend throwing it in the air so he could shoot it with a gun, LMFAO. I cried a little. Was 17.”

Honeymoon Dream

Incompetence tired woman sitting with books and a computer and her hand on her face.
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One Redditor responded, “A girl that I was about to start dating mentioned she really wanted to go to New Zealand at some point in her life (to a group of people, not even just to me), so I immediately priced plane tickets and lodgings to New Zealand for a honeymoon.”

Airbrush Disaster

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An embarrassed user commented, “Let my mom purchase custom matching airbrushed shirts of two people kissing, with my girlfriend and my name on them.”


Sick Woman Laying in bed. Side View
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A disgusting comment read, “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.”

Birthday Break Up

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One Redditor added, “I accidentally broke up with my girlfriend on her birthday because I forgot it was her birthday… I was a catch.”

“You Know”

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An embarrassed person wrote, “I was too immature to talk about us one-day having sex, so I’d giggle and say, “do…you know.”

Total Stud

Older Man Upset crossing his arms
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A user commented, “broke it off because I thought I was a stud. I was single about 3 years after that.”

Source: Reddit

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