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These Are The Very Most Cringeworthy Attempts At Getting Your Crush To Like You

These Are The Very Most Cringeworthy Attempts At Getting Your Crush To Like You
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Updated 1 year ago

For most of my life, all of my attempts at flirting involved me talking about how much I hated myself, or how terrible I thought I was. In my mind, this was a good plan because it showed... something. I don't know. It was never a good plan and looking back on it now, I don't know how I could possibly think it was a good plan. 

As a result of me making countless attempts with this very bad plan, I have to assume that now there are dozens of women out there who all have a story about this weirdo with the worst possible game. I don't mind being the subject of these stories, really. It is what I deserve.

So if you want to hear about my most embarrassing story, ask one of them. If you want to hear other people's, read on. 

She works in marketing now.
I've posted this story before, but here it is.
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.


If this bear doesn't work, nothing will!
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 :/


So... What do you want to do for the next hour?
She invited me for her birthday, but not her boyfriend. And she invited me an hour before anyone else


Imaginary genocide isn't a great pick-up line
Oh man, I wish I'd gotten to this thread earlier.
So when I was like 14, I used to hang out with this guy in my hometown who was really into anime, specifically Bleach. All he wanted to do was talk about Bleach, online roleplay in the Bleach universe, etc. And he wanted me to participate. For some reason I put up with this even though I had no idea what Bleach even was.
So I guess because I was female and paying attention to him and we were 14, he developed a crush on me. Here's how he decided to tell me:
We are chatting on AOL Instant Messenger one night when he suddenly confides in me that he has an alternate personality. It is an evil personality that wants to destroy all humanity. It is probably directly inspired by something from an anime.
I ask if I can talk to this alternate personality. He agrees to "let him out," and then starts typing in complete sentences with capitalization and punctuation to indicate that the alternate personality is really sinister and smart. But apparently not smart enough to realize it could go kill some humans instead of chatting with a middle schooler on AIM.
The alternate personality informs that it really wants to kill me, because I am a human and it wants to kill all humans. In fact, it would have already killed me, if my friend hadn't stopped it through sheer force of will. My hero of a friend had been bravely holding it in check, all this time. "You're lucky he likes you," the evil personality tells me.
I ask to talk to my friend again, and he drops the act with plenty of dramatics about how traumatic it was to let the evil personality out. After a minute or two, when it's apparent that I'm not going to acknowledge his pseudo-confession (my middle-school ass was naively hoping he just meant "like as a friend"), he doubles down. "I can't believe he told you...I didn't want you to find out this way..."
So yeah, instead of just telling me he liked me, this dude made up a fake evil split personality to confess on his behalf in between threats to my life. It is, to this day, the cringiest thing I have ever directly witnessed. But I can't really judge, because I was also 14 and I was just as terrible in my own special way. Weren't we all?


That's, like, the opposite of sexy.
I was walking to class when I heard some loud group laughter behind me. I had my headphones in and there were way too many people for me to want to wander back and find out, so I kept going to class.
I started dating a girl soon after that, and found out a few weeks later that she had dramatically fallen and taken someone else out while trying to catch up to me in the hallway. We had just started talking, and she had worn a cute dress and some heels to get a little bit of extra interest from me. She wasn't the type to wear heels often, so she took a bit of a tumble while trying to speed walk to get to me. Adorable thing she was...


At least you tried...
One time a guy was trying to be cute and zip up my coat for me. He started to raise the zipper, but it got stuck near my cleavage, so he pulled with force. Unfortunately, his hand slipped off the zipper and he gave me an uppercut instead.


He had to know that wouldn't work, right?
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.


This isn't the 1700's, bro.
Not me, but the story involved two of my friends at the time. I was approached by one of my friends one day in the dining hall. He wanted to know if I could help him with talking to a girl I was friends with because he was interested in her. Me, trying to come out of my somewhat introverted shell in my freshmen year was like "suuuure, despite never having even kissed anyone or gone on a date I can for sure offer romantic advice." The guy thanks me and is like cool, I'll get in touch with you via email later. So a day or two goes by and I get an email in my inbox from said guy. He wrote that he'd attached a copy of a letter that he wanted to send to her. I was immediately off put by the fact that a) he wanted to start a conversation via letter like he's Anne of Green Gables or some crap and b) he'd never even talked to this girl before who, might I add, was incredibly attractive and nowhere even close to his league. So, trying to stay optimistic, I opened the letter and gave it a quick scan. What I was greeted with sent me keeling over with tears of laughter running down my face. The dude had written the letter in an old timey style, writing to her in the most "m'lady" way humanely possible. It was full of phrases like "is the playful yet wise personality that I perceive manifested in you, or a consequence of the hormones innate in yet another horny bastard?" After I had attempted to pull myself together, I wrote back quickly, telling him that while his effort was apparent, no one would find this approach attractive. He begrudgingly agreed and a few days later sent me a SECOND letter, in which he compared the girl to a boat and talked about how sexy she was, but like, as a boat. The worst part is that despite me telling him repeatedly to not send this letter, he wrote a hand written copy of the first draft, UNEDITED, and put it in her mailbox after he had graduated.
tl;dr: dude wrote two love letters, one being a poem and the other a boat analogy, to ask out a girl. Put a hand written copy of said letter in her mailbox.
EDIT: a bunch of people are curious as to what happened after she got the letter. Well, here ya go: I was in a club on campus with said girl, and at the next club meeting I see her and she's like freaking out. I go up to her and the other people around her and I'm like what's up? She's like I got this incredibly weird letter in my mailbox, I think it's a love letter. I immediately was thinking no fcking way.* This was a year after I had told him not to send it to her, so hearing this was just like a perfect storm of wtf. So sheepishly I go up to her and I'm like hey, so uh, I actually knew about this. She was like, "WHAAAAT?!" I explain to her that I told him a million times to not send it and showed her the email exchange. Everyone around couldn't stop laughing as she read aloud the letter and all its drafts. She wrote him a very nice letter back declining, but man was it hysterical to see her face when I told her I'd known about it all along.


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