So, when a Reddit user asked, 'What is the cringiest thing you have done to get a crush's attention?' people were ready to reveal the embarrassing or deeply desperate grand gestures they've attempted in the pursuit of true love.
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.' - discoslimjim
In 12th grade I had a huge crush on this guy in one of my classes. I knew his favorite book and movie was Fight Club, so I Googled everything about it (along with watching the movie). On Valentine's Day, I sent him a card that said I want to have your abortion and gave him my phone number. - PregnantMexicanTeens
Thirteen years old, I learned my crush had taken ballroom dancing lessons. Delighted to have something to talk to him about, I proceeded to harass him all of homecoming with what I probably thought was good-natured ribbing. Looking back, I was being an as*hole and straight up making fun of him. Poor guy took it like a champ, but f*cking hell I had no idea how to be social. Sorry, Phil. - flowercurtains
I confessed to her that I liked her friend so she would help me get with her, I did it so I could spend more private time with my actual crush. Worked like a charm, 14 year old me was a genius - that-guy-jack
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. - [deleted]
I started smoking. That mistake lasted 15 years after 14 year old me moved on from that crush. - ThievingRock
I’m running a 5k tomorrow for no other reason than she is and I’m going to have a heart attack... - ialwaysdothis11
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. - remyrf
Sheepishly handed her a letter and ran away in like 10th grade that would have been like a D- rambley mess in speech form that basically said 'Hey you're cool want to hang out sometime?' in three paragraphs because I was nervous as all f*ck and didn't know how to people. Funny thing is that she brought it up again in senior year and asked if I wanted to catch a movie or something. - dkf295
Pretended that I didn't give a shit about them or that I was madly attracted to them. Played it 'cool.' Guess how many times it worked? None. - ninetofivehangover
In high school, I got some presents for my crush's birthday (barely talked to her in person because I was painfully shy, but always talked to her on AIM) Went up to her awkwardly with a red face, gave her the presents, said happy birthday and walked away immediately out of sheer embarassment. She told me later she liked the gifts. - strangehobbies
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. - sociallyineptmilk
We had a foreign exchange student my Freshman year of High school.She was French and absolutely gorgeous, so naturally, all of us boys were smitten with her. She was in choir and sang really well, so I figured since I was a musician as well, that was my 'in' with her.
So, I busted my a*s and learned a love song from a very popular French Opera. It took me a really long time to memorize and I thought it would be a bold gesture. So, I sang it to her flawlessly and asked her how she liked it, thinking that taking the effort to learn a love song in her language would be a great gesture. Well.. That day, I found out that she was Swedish, not French. I'm f*cking stupid. - [deleted]
(I was young!) Called crush's phone every 60 seconds for an hour (no answer, repeat). I figured she'd pick up once she got home and I wanted to talk to her ASAP. Unfortunately, she was on the phone with someone else the entire time, getting the 'you have another call' notifications about incoming calls, just wasn't responding to them.
After about the 60th time she picked up and screamed WHAT!?!?!?!?! and I tried to worm out of it like it wasn't me that had just called her over and over and over. She didn't buy it of course. This one still keeps me up at night 30 years later. - [deleted]
Told her on AIM I had a crush on someone. When she asked 'who?' I waited a bit then typed' you' and signed off dramatically. We did not get married. - [deleted]
I liked a boy in the seventh grade. Every day I would buy a Gatorade and pretend I couldn’t open it and ask him to. One day I did open it and panicked. I tried to close it again as tight as I could and give it to him to open it for me.
He called out on how easy it was to open and looked like it had already been opened. I wanted to climb under the bleachers. - medicalprofessional1