14 People Share Awkwardest Thing They Did In Their First Relationship & We’re Second-Hand Embarrassed

Vasudha Sabharwal

Nothing against people who have had only one relationship that has stood the test of time, but for many of us, first relationships are reminders of the cringiest memories we haven’t been able to come to terms with. You know, that time when butterflies in your stomach made you do certain things and embarrass you for life.


As precious as teenage romance was, it came with a whole lot of things, recalling which now makes us want to dig a hole and hide from the face of the Earth. Well, some people on the Internet have been brave enough to walk the memory lanes to share their most embarrassing memories of their first relationship, and we’re second-hand embarrassed.


1. “We’d get into a fight while leaving a bar and I would purposely lose him and go lay down and cry under a bench until he’d find me. Pretty Cringey.”

– gossipchicken

2. “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.”

– Vebop


3. “We planned, to the minute, when our first kiss would be. Not too bad, right? We were both nervous and it was both of our first relationships. I made a website with a countdown clock.”

– green_green_green

4. “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.”

– ToastBudder


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

– pekoe84

6. “Was walking her home anticipating kissing her for the first time at her doorstep and kept licking my lips because I didnt want to kiss her with a dry mouth. Halfway to her house, she looks at me and says ‘stop doing that’. I realized I probably looked really creepy.”

– SuzukiiLock


7. “Was walking her home in our neighborhood. She says her parents aren’t home. I say ‘Cool, you have the whole house to yourself!’ and walked back home, wondering if I’d ever get a chance to touch her.”


8. “Back in 8th grade, I could not wrap my head around the obvious signals he was giving me that he was not as into the relationship as I was. I was extremely clingy and would draw doodles of us and write the mushiest notes to him. I would quiz him on what he liked about me. Fishing for compliments from him constantly. Making up a new pet name every week.”

– BitchQueenofLich


9. “Tried to have sex. She ended up being a lesbian. Glad I could help her find her way.”

– discoslimjim

10. “My phone at the time was about to run out of storage (this was ~2008) and I had to delete all the saved texts I had from him that included some really cheesy sweet ones, and some dirty ones. So, I wrote them each down one by one on little pieces of notebook paper, laminated them, and hid them inside a Jonas Brothers book (?!?) so I would always have them.”

– cp010116


11. “I became too attached and couldn’t handle the rejection of her breaking up with me, and became a creepy ex who would text her and message her all the time. What makes it worse is that it wasn’t a REAL relationship. We met online, interacted online on skype.”

– perpulstuph

12. “I got my best friend to break up with him for me. I’m so ashamed :(“

– wwjdforaklondikebar



– PaintedSe7en

14. “I faked a cancer scare (or something similar) cause I thought it would bring us closer and our love would be more dramatic like the movies.”

–  mayodayz


We’re not hiding our faces, you are!

You might also like
6 Sexual Health Experts Answered Reddit’s Burning Questions & We Think Everyone Can Benefit From It
I Totally Support Registering For Live-In But Mere Ko Kuch Technical Issues Hain
Orange Peel Theory: Know The Sentiment Behind This Very Literal TikTok Trend
We Made Multiple Contracts For Your Tez Relatives ‘Cos Kalesh Is So 2023
Let’s Be Real & Discuss Signs Of A Scarily Toxic Family That Loves The ‘Hum Saath Saath Hain’ Vibe
10 Women Shared Their Happy Stories Of Getting A Divorce After 30 & These Are Full Of Hope