The Most Cringeworthy Things People Have Done To Impress A Crush

We all have had that moment when you spot your crush looking magnificent from afar, so much that your eyeballs turn into magnets which becomes extremely hard to look away.  Having a crush can make people do crazy things, which usually involves embarrassing situations like releasing uncontrollable nerves or shouting word vomit you never intended to say.

Some people preach that they live with no regrets and I’m calling bullshit.  Trying to make an impression on someone can turn into hilariously regrettable situations and these Reddit examples will prove it.


1. Shit_Down_My_Peehole pretented like he was a Ice Age Character.

When I was little, I saw Ice Age and there is a scene where Diego wakes up and yawns and since he’s a sabertooth, you see his huge awesome chompers.

So, my dumbass would sit in my chair, facing my crush and yawn with a giant open mouth, baring my teeth, hoping to woo in my fair lady. But alas, no luck.

2. Handeatingcat used chalk as his secret prop.

I knew which way she walked home from school, so one sick day I wrote ” I LOVE HEIDI” in giant chalk letters on the sidewalk where I knew she’d pass. I hid in the bushes and when she walked by I yelled “Looook doown!”. She promptly decided to speed walk the rest of the way home, I never told her it was me.

3. Norberthp’s friend made it weird quickly.

Not me but my friend had a crush on her neighbor who was playing basketball in the street with his friend. She put on a bikini, dragged a baby pool into her front yard, and took a soapy bath with her dog. The boys kept glancing at her and laughing

She was 13 and I remember watching it unfold from inside and cringing.

4. Seven_Kostanza had a foot in mouth situation.

I wanted to be her partner when we got in pairs in Spanish class. I was mentally preparing how I was going to ask, but when the teacher said to find a partner I just yelled her first name really loud. People stared at me and she was embarrassed I think. It is one of those times where I look back and still cringe.

5. Humminbug used the classic yes/no/maybe move.

In middle school I wrote a letter to a boy asking him to go see TMNT with me and my friends. I even had the boxes for him to check yes, no or maybe. He threw it away.

6. Assassin451 attempted the artistic route.

I drew a picture for a girl in middle school to ask her out. It was of us holding hands in front of a sunset. She showed her friends and laughed at it with them. 😦

7. Projektmayem had no idea what he was doing.

I tried to sing her a song while playing it on the piano. I can’t sing. I can’t play piano, I just knew the basic tune and knew that the higher notes were to the left on the keyboard. I didn’t even know the words to the song. Looking back, it was pretty obvious she didn’t even want me to sing to her, she was being polite. Oh god OP, why did you make me re-live this memory.

8. Halfwoodenjacket’s situation sounds like the beginning of a horror film.

I bought red roses, got up early, went to her place and placed one rose on her doorstep, one on her windshield, one on her desk at work and one in her coffee cup.

She was a little creeped out.

9. Deathbycommas is still haunted by her mistake.

3rd grade sent a letter to his house, like a dork.

“meat me in the school yard saturday” that spelling error has haunted me for years. he brought it to school and asked if it was from me. i did not sign my name or anything; deny til you die.

10. Teaboomom and hygiene didn’t get along.

In fifth grade I was nothing but cringe. He came to my birthday party so I was in love with him. This wasn’t just a crush, I’d had those before. I wanted him in a way I had never wanted a boy before. Of course, being eleven, I had no idea how to handle these new and confusing feelings. I also didn’t bathe much because I’m slightly allergic to soap and nobody believed me. So, I sat way too close to him, flowed him around, and wrote his name surrounded by a heart on everything I owned so he could see. I also made several threats towards his girlfriend. If I could I’d reach back into the past and give young me a good slap.

11. theLostio’s crush got straight to the point.

This wasn’t for wooing, but I just thought I was being super subtle and discreet when I asked her “If I were to hypothetically ask you if you wanted to date me, what would you say?”. She replied “no” and my heart-broken stupid teenage self somehow managed to answer with “Huh, thought as much, good thing I never asked you then”.

I cringe internally every time I remember that

12. Plsdntdotht forgot that popsicles melt.

In middle school I brought her a Popsicle but was too nervous to give it to her, so I put it in my locker. At the end of the day, after I worked up all my courage, I walk confidently over to my locker and find all of my school work covered in purple goo.

13. Mr_Nexxus tried out Green Day lyrics.

In the eighth grade I printed out Green Day lyrics and wrote “I love you” on the end, then taped them all over her desk and chair.

Somehow, it didn’t work out.

14. Mehdysphoria basically wrote a novel.

I wrote him an essay to confess my love to him. 7 pages worth of cringe.

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