"I asked her out by parking outside her house and writing it on the windows of my car in car chalk. She sent the dog outside and said, "You should leave.
My dog is outside. He's pretty mean." -Reddit user discoslimjim
"My crush was a kid who lived down the block from my house. I stole his dog from his yard and then went to his front door to return it and get to talk to him. He said he saw me take him out of the yard.
I avoided him after that." -Reddit user sociallyineptmilk
"Once, when I was 14, I "accidentally" sent a picture of me in a super fancy dress to my crush because I wanted him to ask me to the dance." -Reddit user remyrf
"I was 15, and I had a crush on this boy for two years. One day a friend of mine told me that he was about to ask me out. He came up to me, said hello, and while anxiety took the best of me, I wanted to look cool, so I said: "Hm, do I actually know you?
Are you new in school?" He instantly turned around and left. We had been classmates since elementary school..." -Reddit user Holy_mouse
"Early college years. She mentioned off-hand that she was reading the Hunger Games.
So naturally, I read the entire trilogy and then tried to bring it up in conversation. She wasn't into me, and that certainly did not help." -Reddit user Bigbennjammin
"Back when I was in middle school, I had a crush and this girl. I was into writing at the time, so I put her in a fantasy story I wrote where she was a warrior. She hated it and told everybody and showed them the copy I gave her.
This did not help my bullying. I still die from thinking about the cringe." -Reddit user (deleted)
"Put an entire pack of Bubble Yum in my mouth and tried to chew it. Ended up drooling on myself.
She left the lunch table." -Reddit user WaffleHouseNeedsWiFi
"When I was in 6th grade, I would yell a lot and be extremely loud when around them.
It didn't work." -Reddit user conspiracyrachel
"I was maybe 14 at the time and saw my crush riding their bike down my street, so I ran to grab a blanket, dashed outside, laid out on the lawn, and pretended to talk REALLY loud on the phone.
(Had to pretend to have a conversation because I had no friends to actually call)." -Reddit user QtipKing
"Oh god, I made a fake Facebook account to post on my wall and talk to him, so it looked like I had made friends.
I hate middle school me." -Reddit user RevolutionAtDawn
"12 years old, she lived nearby. I went to this neighbor kid who had to have been around 7 or 8 and asked that he get his ball and follow me. We got to her house, and I grabbed his ball and threw it over her fence.
Knocked on her door and told her my little brother had accidentally lost his ball in her backyard. It's cringy, but it worked. That was 20 years ago, and we're married." -Reddit user Anefor
"I'm not proud of it, but I used to work IT for a company and had a huge crush on a woman that worked in one of those group cubicle open office designs, so I purposely sabotaged the computers around her so that they'd call me to come up to fix things." -Reddit user niagaraphotos
"I was about 13. I really liked her, yet I had hardly spoken to her all school year. May rolled around, and I finally decided to make a move. I show up at school wearing a nice button-up shirt and combed hair.
For some reason that escaped me, my dad had me bring a bouquet of roses and a card for her. I kinda left them on her desk when no one was looking. Eventually, I didn't have the courage to ask her out and asked one of my friends to tell her how I felt, that I'd suffer for her, bear her burdens, and die for her if necessary. She kindly turned me down, and I ended up crying under my desk." -Reddit user Tandril91
"In middle school, I wanted to give my crush a Christmas present but didn't want it to be weird. So I gave 5 people in my class a gift as well.
When I handed her gift to her, I winked and said, "This one is extra special." The look on her face still haunts me to this day." -Reddit user Ubtron
"When I was in 6th grade, I offered my crush 20 dollars if she would be my girlfriend.
I didn't have 20 dollars." -Reddit user UristMasterRace