10 Cringeworthy Attempts At Romantic Gestures – Don’t Ever Try These

10 Cringeworthy Attempts At Romantic Gestures – Don’t Ever Try These

We’re raised to believe in romantic gestures. Hey, it worked for John Cusack, it should work for us normals, eh?

But alas, life is not a romantic comedy. Often it is neither romantic, nor even a comedy.

A recent AskReddit had people sharing real stories of times they tried to create their own Hollywood ending at it hardly ever works out.

But still: To me, they are perfect.

1. President_of_pigeons on point?

A girl I knew in middle school stabbed two people with a pencil for talking about me behind my back. She was upset when I didn’t thank her

2. Be prepared, the_____. Be prepared.

I was dating this girl for like 1 month. We had a conversation about much we loved ‘The Lion King’. It was playing in theaters at the time – Disney rereleased it in 3D (this is like 3 years ago). So we went to see it and had a great time. After the movie we bonded in our love for the character Scar.

The next weekend we made plans to hang out again. We were sitting in my basement and she told me she had a surprise for me. She sat on my lap with her back facing me and told me to lift up her shirt. I did, only to find that she went and got a fairly large tattoo of Scar from The Lion King. It was hideous. I was very freaked out. I knew it would make it harder to break up with her.

3. Precutfruit got Say Anythinged.

This is long-ish, so hang on. I was recently in a relationship with a guy who lived two hours away. I ended up ending the relationship, and all hell broke loose. Endless calls, texts, screaming, name calling, he really was letting me have it. I politely told him that I was sorry, but my decision had been made and to please leave me alone. I never received any message back, so I thought “okay, maybe he’s finally going to leave me alone now.” Fast forward to about 5 hours after I sent the last message to him. I was sitting in my bedroom in my apartment, when all of a sudden I heard music playing pretty loud. For a split second, I thought it was my upstairs neighbors, as they have a history for playing music pretty loud at times. Then, I realized it’s coming from outside. I almost knew at this point what I was gonna see when I looked out the window. Have you ever seen the movie Say Anything, where John Cusack is holding up the boom box? Well, I open my window to find my ex, standing there with an amplifier hooked up to a random extension cord. He’s struggling to hold it, as it’s a large amplifier. I didn’t know whether I should go outside, or call the cops. I chose the former. Once I got out there, he proceeds to get down on one knee and propose to me. While this is all going on, there are people walking by observing this shit show. Basically I made him leave my apartment, but dammit if it wasn’t embarrassing.

TLDR; don’t copy 80’s movies, you will not get the girl

4. Ayriana is the apple of his eye.

In the 9th grade a guy who liked me wrote a note on a piece of paper and turned it into a paper airplane, which he then proceeded to throw at my head. It hit me in the eye. I had to go to the school nurse and wear an eye patch for part of the day. The answer was no


5. That’s one way to get Oneflan‘s attention.

He stopped me at an underground passage in a train station, asked for charity and then said “Jk, I have been watching you for days and I just wanted to ask you out, and this seemed like the right way to get your attention.”

We didn’t go out.

6. PunkRockBlondie11‘s stories are indeed punk rock.

i have a couple:

messaged me repeatedly on every social media site possible and continued even when I’d open them and not answer. then tagged me in a meme that said “keep calm and love white girls”

asked to hang out with me repeatedly, I politely declined each time. after the like 4th time he offered to clean my house and cook for me while I napped just so he could be in the same vicinity as me.

went on a date with a guy on fourth of july once. the date went really well, and i let him come back to my apartment after. we were making out but i was on my period so kept stopping him trying to go any further, and eventually just flat out told him i was on my period. he said he didn’t care because i was so hot and proceeded to rip my tampon out of my vagina. i asked him to leave after that..


7. Poopmegeese wasn’t into Weird Al.

I had a guy steal the melody from a song that he knew I liked and reworded all the lyrics to be about me and about how much he liked me, my hair, my eyes and my laugh- the last lyrics were him asking for me to be his girlfriend. I was attempting a veerrrrry platonic situation, but we’d been hanging out a lot so I understand how he got mixed signals.

He came to my workplace (a very fancy cancer research center filled with lots of renowned people) and attempted to sing me the song with a ton of important people around. I had to drag him off campus and painfully listen to his song and tell him I wasn’t interested in the slightest.

The worst part was his singing though–I had to hold back laughter making the whole situation worse.

8. TheAnteatr‘s tale is cringey to the highest degree.

When I was 13 a girl had a crush on me. Did I find out because she told me, or because of a friend? Nope. I found out because she made a Powerpoint slideshow about us dating, marrying, and growing old together.

The first slide was about how we met in her imagination, and went on to show stock photos of couples. There was a slide of us on our first date, one of us getting married, one of us having kids together, ect. This was a full one slide show with pictures and cheesy word art. I don’t remember how long it was, but I think about 10 slides. I clearly recall the last slide being an old couple and it said something about us growing old together and bring in love the rest of our lives.

As you can imagine I was not the first to see it. Many other people had seen it and it had been circulating for a few days before a couple of my friends pulled me into a classroom and showed me one day, laughing the entire time like good friends do. From then on anytime I was around her it was awkward. I didn’t have feelings for her before the Powerpoint, and afterwards was creeped out and had a bit of an aversion to her.

9. Did Emzzo get to keep the bear?

In high school a friend of a friend made me a build-a-bear that said ” [my name] I love you, will you go out with me?” And presented it in front of our mutual friend groups. I was so shocked that I couldn’t find the words to reply, so after a solid minute of stunned silence he trashed the bear, fled the school, and didn’t come back that day– still feel bad about it 10 years later :/

10. Throwwwwwingdaway‘s story is Cringe: The Musical.

I dated the most egocentric dude in all of New York. His dad is a famous musician, so he’s lived a life of yes-men surrounding him and whatever toys he’d like… this has resulted in him believing without a shadow of a doubt that he is super talented at everything. Spoiler: he’s not.

He knew I wasn’t interested in him. I told him gently at first, then firmly, then flat out. I’m hanging out with my friends one night and he FaceTimes me… he had somehow clipped his phone onto his guitar really close to his face, and was live streaming his band practice at me singing directly into the guitar camera. It was a really bad angle, the music sounded terrible, his expression was just SO into himself, and I ended up ending the call after my friends got a good laugh because I felt such intense second hand embarrassment.

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