1. Tried to razor scooter down the steepest hill around. Crashed into the back of a funeral hearse and shattered the back window. There was a body inside and the family was outside waiting to either go to the cemetery or take the coffin inside. I got up, covered in blood and glass, grabbed my scooter and hobbled away to the nearest alleyway.
2. I made sure I was the one to return her jacket when she forgot it at school. When I gave it back to her the next morning she blamed me for stealing it, we didn’t end up together.
3. I was a teenager and my crush walked up next to me while I was going through my bag, the sun was in my eyes and I had a crazy thought that having the sun in my eyes would make me look beautiful. He walked away after two seconds and I had a black spot in my eye for two days.
4. I was the first high schooler she knew who got my license. I drove us to hangout with friends of hers. Mostly guy friends, I guess she was trying to date one of them.
5. This past year I threw a fairly large college house party just so the guy I liked could attend. I didn’t want to show him too much favoritism, so I tried to run around and talk to everyone as I was the main host. Luckily my best friend kept him company, and acted as my faithful wingwoman. The night ended with me and my crush talking outside, getting closer and closer.. until he asked me if I threw the party for him. Even being drunk didn’t soften the blow of straight awkwardness. I tried to laugh it off and deflect but I’m a terrible actor lol. Looking back it was kind of obvious the entire party was an excuse to see him, and I now understand why I liked reading The Great Gatsby so much in high school.
6. Got a tattoo to impress a girl in my psych class. It did nothing and now I have a piece of shit piece by a guy named Philly Steve on my leg forever.
7. Tried to backflip from a 5m diving board, there was no flipping involved, just me falling on my back into a pool from 5m high. Shit didn’t feel good, don’t know which one was more bruised, my back or my ego…
8. Caught a couple of buses and went to a mall which was a city away just to get her favorite cupcakes.
I had to careful calculate my trip so I could get them to her during her half an hour break at work.
To not throw her off guard, I had told her that I had passed by the mall to grab something else and just happened to be in the area where she worked.
9. Wore the same clothes as her boyfriend.
10. Got my nipple pierced.
11. Watch TV shows, then pretend to like them because they did. I never want to think about Supernatural ever again.
12. I lost two and a half stone, and then it turned out he was into large girls, damn.
13. Buy concert tickets for PINK who I had zero interest in really but she did, ask her if she wants to go, drove 70 miles to pick her up, 110 miles to the show, 110 miles to drop her back, 70 miles back home.
14. I thought she wanted someone confident. She just thought I was cocky. I also would talk about the girls I had slept with to try and make her jealous.
15. Endured over two hours of shitty dubstep at a “concert.” We did hang out for, like, a month, but I just couldn’t get over her musical tastes. She also loved the most inane movies.
16. Signed up for a french class in high school because a girl I like was in one. Turns out she was into me too, but my dumbass signed up for French 1 when she was already in it and the following year she was in French 2 and I was sitting all alone in French 1 in a class I didn’t care about.
17. Came within a hair of transferring colleges across the county just because a girl went there that I had a crush on who didn’t know I liked her. Thank God I wised up.
18. I pretended to like going to church, joined the youth group band and got baptized. I had a huge crush on her. She ended up going to prom with me then never talked to me again.
19. I hoarded a bunch of stuffed animals I won at a local arcade over the summer for this girl I really liked. One night, I thought, you know, tonight’s the night. I’m going to surprise my crush with all these stuffed animals, and she’s going to fall in love with me. So, I threw them in a white garbage bag, walked two miles down the road to her house during sunset, and knocked on her door. She answered the door while I concealed the bag of goodies behind my back. She awkwardly asked what I was doing at her house and I revealed the surprise. She slowly grabbed the bag from me, looked inside of it, and gave me an awkward thanks while closing the door. Right then and there, I realized I miscalculated the gesture and probably looked like a huge creepy fuck. I power-walked back home and to this day, I still think about it from time to time. I think it’s my brain’s way of punishing me eternally for putting it through that whole thing.
I’m loaded with stupid stories like this one because I am a huge romantic and I tend to get bitten in the ass in one way or another because I just don’t see clearly when I’m in the haze of being in love…
20. I tried reading the fucking Twilight book. I was so dumb.
21. My sophomore year of HS, I asked a girl out on Valentine’s Day by having red, pink and white carnations delivered to her homeroom. I walked by her homeroom, and my buddy gave me the negative headshake. Already disappointed, she came out and told me she had a boyfriend and asked me if understood. She kept on repeating “Do you understand?” repeatedly. In retrospect, I probably had the “deer in headlights” look on my face.
The worst part was that I was pretty confident about her saying yes and had told all my friends about it. The train ride home that afternoon was pure hell as my friends razzed me non-stop for the entire ride. In my defense, she had invited me to her birthday party a few weeks before and her boyfriend wasn’t there and he wasn’t brought up at all. So…yeah. To say I was gun-shy after that would be a major understatement.
22. I intentionally threw multiple games of Uno to let a girl think she was amazing at the game.
23. Started smoking. Wanted to look cool and have an excuse to talk to her, it worked but we only dated for a couple of months. Biggest mistake of my life.
24. Embarrassing to admit but the only time I truly tried to impress a girl was in primary school when I was about 10 or 11, I would swear when she was near and always gave the impression I didn’t give a fuck. Backfired though, she just ended up thinking I had anger and behavioral issues.
25. Learned how to rap Crack a Bottle by Eminem… when I showed him I could tell he only knew the clean version and I knew the actual dirty version.
26. Ran into a busy road and picked up a hedgehog. Wasn’t run over, but my hands stung for a week.
27. Really loud shitty music in car while giving her a ride.
28. Went to donate blood with a girl… She didn’t donate due to iron deficiency… I saved 3 lives.
29. I bought a hedgehog off someone to give to her, but her parents said no. I ended up keeping him and he was the sweetest boy. Lived for 7 years!
30. In middle school I asked a girl out by commenting “Will you go out with me?” one word at a time, each on a different post of hers and in reverse order so that it would read as the full question in her instagram notifications. She told me it was the most romantic thing anyone had ever done for her. I didn’t really keep up with her after that year so idk where she is now but I know I set pretty impossibly high standards for her future boyfriends.
31. Drugs. Idk how well that really worked but it was definitely a mistake.
32. My high school crush said she would only date older guys, so in a bid to impress her I concocted a story whereby I was supposed to be two years older than my classmates. Unsurprisingly, this didn’t get me any closer to seeing her naked and I had to maintain the facade to my school-friends that I was two years older than I actually was.
33. I became fluent in Swedish only to find out that he was Swedish by birth but did not actually know the language.
34. When I found out that the guy I like broke up with his longtime girlfriend, I lost weight and changed how I look and about to make a move. Only to found out, he already got back with his girlfriend.
I cried for weeks and did not want to go to school.
35. Bought a Rolex for the second date.
36. My high school crush wore a Pink Floyd t-shirt so I listened to all of Pink Floyd, memorized lyrics, and then recited them to him as responses when talking to him.
37. I went to every party he was at. I don’t like parties.
38. The guy I liked my senior year of high school was a huge Chicago Cubs fan so I went to champs and bought every V-neck cubs shirt I could find (I’m large chested). Unbeknownst to me, a friend ended up telling him I bought them so he would notice and the next week he saw me in the halls and pointed out that my shirt looked way too tight. I actually just bit the inside of my cheek.
39. He mentioned he liked this little independently owned pizza place across town. We were in college and I didn’t have a car, so I took a bus across town to pick up this pizza and bring it to our informal club meeting. Took like an hour round trip on the bus with a giant 18” pizza, and it was definitely cold by the time I got there. Offered him some and he turned it down— I later learned that he was a super picky eater and didn’t like any of the toppings I got. One of my friends helped me eat the pizza.
40. A girl I liked played soccer. So she was around when my games were on.
I’d purposely take a hard fall when she walked by just to get her attention. It worked. She asked if I was okay. I was.
She dated some really old guy in high school and moved to… California?
41. Went to a non-denominational church with a girl I was trying to bang. I grew up catholic, but don’t consider myself religious at all. That place was batshit crazy. People looked weird and as I looked around, people were looking at their phones or speaking in tongues. The pastor was also condemning homosexuals and speaking in tongues and when he didn’t know what to preach next. He brought up a moment in his life were he was tempted by a gay guy, but the power of Jesus saved him. Also, for whatever reason, all the middle age ugly balding dudes had younger knockout wives. Needless to say I didn’t get to bang her. I’m sure I dodged a bullet.
42. In high school, a few hours after school was let out, I was talking to this guy I had a crush on when he mentioned he left his Spanish notebook in his locker and had a test the next day. Since it was a regional high school and he was far away and I was close, I offered to help him out. I walked a mile to the school, went to his locker, called him, got the combination, and read 10+ pages from the notebook to him while I sat on the hallway floor and he took notes.
43. Went to an anime convention with her. Didn’t enjoy the social interactions one bit, but somehow the whole event managed to pique my interest and I started watching anime. Am now fluent in Japanese.
44. Went to school, started a business, worked my ass off, went back to school, moved up in the world, bought houses, investment properties, businesses; she’s still not impressed.
45. I memorized the complete poetical works of Robert Frost.
46. I wasn’t good at sports, but I was fairly quick, so i joined the track team to impress a girl. Turns out the girl wasn’t impressed by runners, but I did end up going to state in the 100m dash and placing 2nd.
47. Well…. When I first got with my (now husband) I wanted a change so I dyed my hair jet black. I’m very, very white. I don’t fucking know why, but I used the boxed dye on my eyebrows too! I looked like a fucking freak and I thought it was so cute and he’d love it. What the fuck is wrong with me.
48. On a 4th of July date after going out to dinner, I took her out on the lake in a canoe to watch the fireworks. It was awesome.
Young macho me, of course, turned down her offer of help with a large canoe and I manhandled that thing like it was nothing. Put her in it while it was on the grass and continued manhandling it to show off just how strong I was.
The next morning i had to call in to work sick because my back muscles were so strained I couldn’t get out of bed. My back was sore for over a week!
49. I tried to do a backflip. I’ve never actually done a backflip before, not even on a trampoline. I actually would up just jumping backwards and hitting my head hella hard on the ground, and then I woke up and threw up a bunch. If she ever had a thing for me (which all my friends said she did), it was gone that day.
50. I was abroad in Dominican Republic, they had a dance competition on a stage, anyone could enter and it had around 200 people watching. I was about 9-10 ish and spotted a cute girl who must’ve been around 14-15… So obviously I decided the best way to get her attention was to get up on stage and dance my heart out. Queue 3 minutes of awkward shuffling, while maintaining constant eye contact with that girl, and horrified/queasy looks from my parents. The coordinator cut me off early by pretending the speaker stopped working. I got a pity clap.