You Did What?! 26 Hopeless Romantics Reveal The Most Cringeworthy Thing They’ve Done To Woo A Crush

Granted, most of these stories lie in the realms of adolescent awkwardness. Doesn't mean we can't laugh at them now though!

Flowers Mysteriously Show Up at Her Door

Picked flowers at night, put them in front of her door. Not even a note, or a name, or anything, just the flowers. Even denied it when she asked if they were mine… Don’t know what I was trying to accomplish there… (Source)

Not Even Green Day Could Save His Plan

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. (Source)

Her Essay Would Have Gotten an A from the Teacher

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

His Love of Dragons Tipped Her Off

I was really into dragons growing up. Like really into them. I had a book called Dragonology, which I had with me all the time. In the book there was a language key for “Dragon Runes”. Well me being my sly mysterious self, I wrote her a love note in these runes with a little key on it so she could figure it out. Didn’t say it was from me. I slipped it into her locker and she confronted me the next day. I was amazed that she knew the note [the one written in dragon language] was by me [the kid that was obsessed with dragons]. Thinking back I must’ve come off like a greasy haired zodiac (Source)

He Yelled Out, and She Rushed Off

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. (Source)

She Didn’t Realize She Was Baking for Two

I worked in the office at a construction company part time at 17. I’m a flirt anyway, but there was one young guy I actually had a crush on so I always thought he was flirting with me. For his birthday I found a doll sized truck that looked exactly like his and baked him a cake shaped like a garage with the truck inside. Yes it was difficult and time consuming. “Wow this is amazing. My wife is gonna love it too and probably want to know how you did this.” (Source)

He Cutely Copies a Saber-toothed Tiger Move

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 dumb_ss 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. (Source)

He Just Wasn’t Cool Enough to Her Ears

She was already in the process of giving me the “thanks but no thanks”, and in a bit of desperation I tried serenading her with some sweet No Doubt over the phone. 18 years later and we are happily married… to other people. (Source)

Being Too Loud Sinks His Dream

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. (Source)

Coin Humor is Just Plain Corny

For the purposes of this post, my name is Mark. I saw a coin on the ground while talking to a girl, and decided to show off how “cool” I was in a humorous way. “I don’t know why everyone thinks I’m so cool at everything I do. Hey look, a penny!” I picked up the coin and then started celebrating. “Go Mark, go Mark, it’s your birthday! It’s your birthday!”
The humor being that I was oblivious to being cool at even the little things, like picking up coins. F_ck I was horrible. (Source)

Mystery Roses End Up Being Creepy

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. (Source)

He Came THIS Close to Getting Close to Her

Join a club at school. Then spend a bunch of money I didn’t really have to spend on going on a club related trip. I hoped it’d be my shot to get some alone time with her and make my move but she ended up pulling out of the trip and I didn’t know until we were about to leave….. (Source)

He Got the Hypothetical Answer He Hypothetically Dreaded

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. (Source)

No Talent, But He Earns an A for Effort

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, why did you make me re-live this memory. (Source)

His Antics Made Her Clean Up at the Audition

In HS, we were at call-backs for auditions for the school musical. Girl I was interested in was sitting in a chair backwards (think AC Slater style) while rehearsing her song. Genius idiot me decides that a great way to grab her attention is to football hike this 32oz shampoo bottle at her. So I grab it, yell to get her attention, and hike the bottle as hard as I can through my legs. The bottle hits the back side of her chair. Luckily it wasn’t a few inches higher or it probably knocks out a few teeth. Nevertheless, the impact with the chair explodes the shampoo bottle and she is completely covered in Pantene Pro V shampoo, just minutes away from her callback / audition time. I guess it worked though, we’ve been together for 12 years now, married for 3. (Source)

She Thought She Crushed It for the Sadie Hawkin’s Dance

We had a Valentine’s Day thing in high school with Crush cans. You know, the drink? You paid a dollar to have a can sent to someone. Orange Crush was for friendship, red Crush was for love, and purple Crush was for, well, a crush. I sent a red Crush to my brother because I’m a rude little sister. That was great. Tee hee. But then I sent a purple one to a guy I liked, asking him to the Sadie Hawkin’s dance. I’m pretty sure he was pressured into saying yes, considering the can was delivered in class… … Needless to say, he kept making excuses as to why he couldn’t go… (Source)

She Hands Over Her Heart and Her Cool Treasures

“Hey, I really like your bracelet.” “Thanks…I’ll give it to you if you go out with me.”
“…sure…” gives over bracelet I wish it stopped there, but no. I went home that night all excited about my new budding romance. I had these two drawers where I kept all things I thought were “cool.” So I found this brown paper sack and I put in some cool stuff…a kaleidoscope, a dollar, those popper things you got from the video arcade stores, some other stuff. And the next day I come into school, see my crush sitting against the wall in the gym. I make eye contact with him and slide this paper sack right to him and keep on walking. I totally felt like I was working a pretty good game in that moment. But he broke up with me later that day. Ah, the perils of 2nd grade. (Source)

Why Drugs and Romance Don’t Mix

So I was at a house party, drugs were involved. There was a girl there who I liked and had been talking to quite a bit. She also had a couple of other guys chasing her. Luckily I had coke and got her to come upstairs for a line. In my coke addled head I was planning on saying something funny/romantic along the lines of me being infatuated with her like I’d caught some kind of illness. Honestly I don’t know what I was thinking but seemed like a f_cking great idea at the time. So I get her upstairs and we look into each others eyes and i splutter out “I have a…. disease….” At which point she went wide eyed and all but ran out of the room. (Source)

Cutlery Inspires Cheesy Pickup Attempt

I had the stupidest, cheesiest, not-so-classy pickup line ever. I had some cutlery; a fork and spoon to be exact. I walked up to them, and while raising up the spoon, I said “Wanna hang out and spoon with me later?” and then, while raising up the fork, I said “or would you rather fork?” I’m pretty embarrassed just thinking about it, but at the time both of us thought it was hilarious… (Source)

First Kiss Makes Him So Nervous He Put His Fingers…

We were sitting on a swing together. She was leaning against me and I was so incredibly nervous. I’d never even kissed a girl before. She looked at me longingly and I knew it was coming. I reached up and gently touched her lips. Trying to convince myself I could get the courage to just kiss this girl that so obviously wanted me to. My brain was in full on panic mode. I’d never had a panic attack before but it was definitely happening now. I had completely short circuited, slowly pushed my fingers into her mouth and started feeling around inside her cheek. She was so confused she just kind of looked at me sideways like a cat trying to figure out how you’re making the blanket move. I removed my fingers and she got up and walked away, pausing once to look back at me expecting an alien to have taken my place. I never had the guts to talk to her again. (Source)

She Really Lit Him Up

In my 20s (sigh) I was teasing a guy I liked by pretending to set his hair on fire (alcohol and drugs may have been involved). Problem was, he had some hairspray or gel in his hair, which I didn’t know… it actually went up. Thankfully it put itself out before hurting him. He did marry me later, but my GOD he will never shut up about the time I set his hair on fire. (Source)

He Weaponized a Chocolate Pie to Win Her Love

When I found out her college professor was relentlessly hitting on her during class, I burst into her classroom and hit him in the face with a chocolate cream pie. He chased me out of the building and about 2 blocks down the street before he gave up. I made quite an impression – we’ve been married 30 years. In retrospect, actually not so cringeworthy. (Source)

Prom Date Turns Awkward When She Pulls Out a…

I went to prom with a friend who I had been crushing on for all of high school. We were driving home afterwards, I was digging through my purse, pulled out a condom, saying something along the lines of “Hahaha how did this even get in here?!” I was not an overtly sexual person at all, so it was pretty clear what I was implying. At that point we had to have a very awkward talk about how he really, really, really doesn’t see me in that way, for the rest of the drive home. (Source)

He Wrote the Book of Passionate Love…Literally

I wrote her an illustrated, leather bound 450 page book on which I bared my soul. I was 38 years old at the time. I wish I was kidding. (Source)

George Costanza Would Love This Hair-brained Banana Scheme

In my first year of college I was living in residence and I met a girl pretty frequently. We had made a quick connection and even made out a few times. ANYWAY college moves quick, so after a few days I started to notice she had started to lose interest and started to disappear on me. So I hatched Costanza-esque scheme of leaving Bananas in her dorm room so I would have an excuse to come back for them. So the next day I was texting her an getting very luke-warm responses (good/k/alright/) so I figured it was time to hatch my banana plan, but I didn’t quite figure out how to word it. I ended up trying to be kind of silly about and texted her “Hey. Mind if I mozy on down and snag dem ‘nanners”. She never responded and I never snagged dem ‘nanners. (Source)

He Tried to Become Famous Overnight

When I was 14 I made a fake website for a fake movie to prove to a girl I was starring in a movie. (Source)