Cringeworthy Memories When People Tried to Woo Their Crush

20. Ruining Her Audition for the School Musical

You cannot deny that, at least once in your life, you’ve done something absolutely mortifying when you tried to impress the person you liked. And if you did it, we bet you cannot compete with these cringeworthy stories from a very hilarious Reddit thread started by whatsausernamefor in Ask Reddit: “What is the most cringeworthy thing you did to woo your crush?” Many of these stories seem to mirror our memories, but you should know that some of these people even got married to their crush after what they pulled off! Get ready to be amazed!

“In HS, we were at call-backs for auditions for the school musical. Girl I was interested in was sitting in a chair backward (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.” - Reddit user kukukele That was an epic fail that - don’t ask us how - actually ended with them becoming a couple! We guess miracles exist!

“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 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." :/” - Reddit user NikitaVanBuren This poor girl thought she had herself a boyfriend, but he was actually married and didn’t wear his ring so that it wouldn’t be cut off in an accident.

“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.” - Reddit user body_talk The girl pretended she didn’t know him, but was thankful to be saved like this. So we can say pies are the recipe of a happy marriage?

“I was really into dragons growing up. […] 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 […] was by me […]. - Reddit user MistaTom MistaTom was really mysterious when he was a kid! How come he didn’t think that through well enough? He must have been very in love…

“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.” - Reddit user [deleted] The cringe moment starts with you saying out loud that people think you’re cool. But the little show with “go Mark, go Mark” had us in tears!

“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.” - Reddit user AtHashtagThrowaway At least this guy has found his soul mate, who would probably accept a phone serenade from time to time.

“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 […] 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.” - Reddit user projektmayem Remember those funny documentaries with birds putting everything on the line to impress a potential mate? At least they knew what they were doing, projektmayem!

“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.” - Reddit user Seven_Kostanza Way to act cool, dude! His brain didn’t get the message he had to be smooth so that he could accomplish his plans. Poor kid…

“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.” - Reddit user Handeatingcat We don’t understand why she got scared? Ladies love guys who jump out from bushes, yelling at them for no reason!

“I found myself giving her rides to events and hang outs with mutual friends in High School, made a mix cd of songs that I thought would subtly imply my affection for them. She realized what I was doing within ten minutes, thought it was hilarious, and judged me hardcore on my desperateness and poor taste in music.

We got married in December.” - Reddit user Rom709 Most of the times, no matter the gender we are, we all like to hear someone really goes above and beyond to impress you. Even with strange mixtapes.

“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.” - Reddit user theLostio Teenage theLostio was really smooth that time, and while he thinks it’s a cringeworthy memory, we believe he had a great comeback.

“Pick flowers at night, put them in front of her door. Not even a note, or a name, or anything, just the flowers. Even denied when she asked if they were mine...

Don't know what I was trying to accomplish there...” - Reddit user asldfbaslfbawlfyb This is our cats bringing dead birds on the porch all over again! They also left no message, but we had some strange eye contact…

“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.” - Reddit user Mr_Nexxus You try to make a good impression and she’s just mad she has to remove all that paper and tape off her chair and desk?

Ungrateful much?

“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.” - Reddit user Plsdntdotht You should have seen it coming, mate!

How can you not realize it’s going to melt after all those hours?

“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.” - Reddit user halfwoodenjacket If you skipped the coffee cup part, you’d probably have had a better chance. But still, it was creepy!

And you did it as an adult! It’s twice as creepy!

“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 till you die.” - Reddit user deathbycommas Now let’s not get all judgmental, it was 3rd grade after all! There are a lot of adults out there that don’t know how to properly write. But the meat part was funny nonethess…

“I was class representative in high-school, and one of our tasks was the class seating plan. Sooooooo I chose a comfy spot, in a corner, and put him right next to me.” - Reddit user frenchybop When you yield great power, you get to make life-changing decisions!

Redditer frenchybop seized the opportunity, and the poor guy had no idea about what was actually going on!

“I wrote him an essay to confess my love to him. 7 pages worth of cringe.” - Reddit user mehdysphoria We really want to see that essay, but our guess is she didn’t think of making a spare copy… We have one important question to ask this redditor.

Was it front and back?

“Whipped a lacrosse ball towards her from across the gym. Hit her right in the noggin. Ended up dating.” - Reddit user shoffster Hitting your crush in the had might remove her ability of thinking straight and accept to date you afterward.

Or at least that’s what this Redditor taught us. Seriously, don’t hit people.

“In first grade I gave him a love letter asking him to marry me. He said no in front of all of his friends.

I was humiliated.” - Reddit user tjdraws This redditor revealed in a separate comment that it all happened in 3rd grade. Maybe the guy had other priorities… Some people are never willing to settle down!