50 Boys On The Dumbest Thing They’ve Ever Done For A Pretty Girl 

1. First girl I asked out I left a chalk outline of a body on her driveway, along with a (clearly fake) police report indicating I was dying to go out with her. Yeah. I still cringe at the memory.

2. Enrolled in the same Uni, she stopped talking to me 2 weeks later.

3. In high school this girl who I was close friends with (but also had a not so secret crush on) told me once how she really loved those HUGE 7 foot tall teddy bears, so I told her one day I’d buy her one and she laughed, writing it off as a joke.

Fast forward like 3 years later when we’re going to the same local college and reconnected after slowly drifting apart after high school. She tells me one day that she’s sick so I do the only logical thing. Drive to Costco after class, drop 200 bucks on that huge teddy bear, stuff it into the backseat of my tiny Honda Civic, drive incredibly dangerously since the bear is taking up my entire rear window, then show up at her front door. She says it feels too weird and romantic given our past (me having that not so secret crush back in high school and her having to tell me multiple times that we’re better off as friends) so I do the whole drive back and return the bear.

4. Grew my hair long because she asked me to. She stopped going out with me. I kept growing it, and wasn’t successful with women until I got it cut.

5. Was in a long-distance relationship with her. Flew back for Valentines day, turned up with flowers… to see her through the window, sitting on the lap of her ex.

6. Fought with a hater in a comments section on one of her YouTube videos. Girl didn’t like I was getting into it with people on her videos never asked me to stop just went to our principal almost got suspended for it.

7. She somehow convinced me to break up with my gf (she was super flirty and I began to have feelings for her). Turns out she was just playing with me.

8. I let my high school girlfriend drive my car, and she rear-ended someone at a stop light. She panicked, and talked me into swapping seats with her and talking the blame for it. So she wrecked my car, and my driving record.

9. Wrote a fucking poem in a word document and emailed her.

10. Agreed to move into an apartment with her that was 40 miles away from my workplace (it was very close to her workplace). I spent 2-3 hours round trip in the car every day for over 2 years. I didn’t regret it at the time, but now I have a much shorter commute and realize how exhausted I was by the terrible commute.

11. Paid for a girlfriend to go on holiday with me to see my father in Singapore. I used all my savings from the shitty weekend job. She was my supervisor but apparently didn’t have any money.

Turns out she had over 4K in the bank but she just wanted me to pay for it all. She cheated on me with the guy she said she hated and I walked in on them fucking 2 months later.

12. Cute girl challenged me to race across a body of water. I barely know how to swim and almost drowned. 2 years later, same thing, different girl.

13. Spent $7500 on a car for her. It was a VW Golf she had always talked about wanting to buy. She wrecked it less than a month later on her way to one of her other boyfriend’s house… Karma is a pain.

14. I tried impressing a girl with fire. Ended up being rushed to the hospital with burns all over my hands and arms. I got a pity hug a couple of days later by her. No regrets.

15. After I met my college crush, and got to know her better, every single day after the classes after finished, I used to roam through the entire college just to find her, and I didn’t want to call her so I don’t look like a creepy guy, now I back and realize how stupid I was.

16. Drove to Denver from Vegas to see a girl I was in long distance relationship only to get stood up and also receive texts from an unknown number (that turned out to he her boyfriend) telling me I’m ugly pathetic POS and I was an idiot for thinking she’d want to see me.

17. Converted to Mormon. Long term, long distance relationship. She dumped me shortly thereafter. I dumped Mormonism shortly thereafter.

18. Flexing my non-existent muscles any time she was in the room so hard I burst a blood vessel in my fucking eye.

19. I skied down a steep slope to retrieve a girl’s lost ski pole and ended up flopping down the slope and tearing my ACL in my left knee.

20. I gave my trust to a girl who was still keeping contact with her ex. Yeah, that relationship didn’t end really well.

21. I let an ex girlfriend move in with me because she wanted freedom from her mom at home.

She fucked some other dude in my bed while I was at work.

22. I stayed with her after getting cheated on… multiple times. Guess what was cheated on again. She decided that she would cheat with my best friend… who was living in the same place. Maybe proximity played a part in it? Anyway cheaters cheat. Not to be trusted.

23. I made a mix tape of me singing 90’s cheesy love songs.

24. Into this hippie chick I college. The moment I found out her and her bf were having issues I spent over $200 (basically everything I had as a broke college kid) on tie dye clothes and grateful dead apparel.

End of the day, we ended up dating for about 1.5 years.

25. I bought a girl an iPod Touch to try to get her to like me. Its one of the cringiest things I ever did in my life.

26. In High school, I made 100 paper cranes and put them in a box as a gift for a girl I liked. I tried to ask her on a date while explaining the box and its contents.

She took the box, smiled and said thanks, but we never went on a date.

27. I was lead on and friend zone by a girl not too long ago. She made it seemed like she was interested in me but in reality she only wanted emotional comfort. The stupid thing is that I’d cancel a lot of my plans just to be with this girl. Only for her to bail on me and sleep with other people. Now she’s pregnant and engaged to some dude she met a few months ago.

28. The stupidest, lamest, most ridiculous thing I ever did was say “bless you” to a girl who hadn’t sneezed because I for some fucking stupid reason thought it’d start up a conversation.

It did. The conversation went “what? I didn’t sneeze” “oh… my bad.”

29. She told me she needed some time to think. After a week I gathered a basket, put flowers, chocolates, toys and treats for the cat, and a heartfelt letter about how I felt about her in it. Then left it on her doorstep.

She blocked me on her phone.

30. Her homework. (For real. In 3rd year of university. Also ended up cat sitting for this same girl at her apartment, despite not having a car or public transport.)

31. Bought a game just so I could play with her…. Didn’t know her boyfriend would be playing with us as well. Rip 50€.

32. I intentionally threw multiple games of Uno to let a girl think she was amazing at the game.

33. Agreed to date her even though she “wasn’t ready.” Didn’t know at the time that meant I’d just be her filler dick.

34. Not me but back in middle school a friend of mine made a graffiti on the wall of a girl’s house in the middle of night, saying he loved her. He misspelled her name.

35. I lost 70 pounds. Still didn’t help.

36. Did it yesterday, after her telling me she doesn’t know what she wants and that she doesn’t think she wants a relationship right now, I left flowers on her doorstep with a card thanking her for the fun times we’ve had.

37. Moved across the US (East Coast to West Coast) for her, when I really wanted to go back home to Asia. Broke up with me after a year.

38. I once pretended to be drunk and I flirted with her best friend to try and make her jealous and then because of that she said that I wasn’t who she thought I was and she stopped liking me. I wanted to make her think I was cool but instead I made her think I was an ass.

39. The girl I lost my virginity to. I thought it was love but looking back it was pure lust.

40. Started smoking cigarettes.

41. I made a rap. No, I genuinely am too cringed about it to post it.

42. I told my university aged (now boyfriend) before our first date that I thought he looked cute in his high school uniform (had been looking at old pics) so he rocked up to pick me up in his full school uniform that barely fit him anymore.

43. Gave her a chocolate bar with the golden ticket to go out with me… I got denied.

44. This girl I really likes ages ago didn’t really know who I was. I gave her a Wii for her birthday and it was probably the creepiest thing ever to her. I thought it was a sure fire way to win her heart, get married and all that Disney crap.

45. Moved across the country to go to a university near her. She dumped me 4 weeks later. PS – my life turned out great as a result of my decision to attend this school so it has a happy ending.

46. Getting up from the bleachers to play PE dodgeball, I tried to pull my sweat pants off while yelling “LET’S DO THIS!” Ended up yanking off everything, boxers and all.

47. Traveled an hour and half multiple times a week to go see her, she never did the same for me and she eventually ghosted me.

It was probably one of the most pathetic and cringy times in my life but I learned a lot from it.

48. Smartphone contract… 2 years 45€ monthly… After 6 month she left me… Now I have 2 phones and 70€ to pay every month…

49. She crashed her bike going down a paved road so I did the same to impress her (or to make her feel better, I really don’t know my reasoning). She landed in the ditch. I did not.

50. I let another kid punch me in the face, it worked.