What is your most cringe story about someone who has/has a crush on you?

When I was in college in first year I joined a few nerdy societies, wargaming, roleplaying, that kind of thing. During the day I dressed kind of frumpy, Jeans or and loose fitting t-shirts that hung off my curves and made me look more overweight than I actually was and projected the image.

Of course, for nights out it was a different story, and I would wear contacts, lots of make up, tight skirts and low cut tops that showed off my tits and ass, and often went home with guys. My close friends used call me "Slutbynight" because the joke was I was a prude by day and a slut by night. When I ran into people from college in nightclubs they would often take a while to recognise me. I got better at presenting myself day to day as college went on, but in first year I was more interested in getting an extra hour of sleep in the morning than looking hot.

Anyway, there was this one guy in the Roleplaying club who, to be honest, was a bit of a neckbeard. He was one of the in crowd in the club, and he was really nice to me after I joined, always taking the time to include me in games, always stopping and chatting when I ran into him around campus. He wasn't creepy or anything, just notably nicer to me than all the other new members. I didn't do anything to discourage it, I knew he liked me, but I just decided to accept his kindness and try to be his friend.

The one time he didn't stop and chat to me was when I walked past him one morning when I was on a walk of shame. He took a good look at my tits in my lowcut top, but he didn't actually recognise me.

Anyway, a few of us went for a few pints after one roleplaying session and after a couple of hours our small party had dwindled to the point it was just the two of us left. He steeled himself and asked me (shortened and paraphrased) "Maisie, I think I love you. You don't have to say anything now, but I hope you'll let me prove my love to you and one day, it would be amazing if you could love me back and we could lose our virginity to each other"

I was kind of stunned and surprised and creeped out and all I could think to say was "I'm not a virgin."

Now he looked stunned and asked "What? Who did you have sex with?"

I was very annoyed at this point at the invasion of privacy, just told him "I don't think you'd know any of them."

"Them? How many was there?"

"That's none of your business." I said icily, quite pissed off now.

"Sorry, I just didn't know you were a slut"

I got up and left. After that we avoided each other. He started telling everyone in the club that I was a slut, which thankfully no-one gave a fuck about, least of all me.

/r/AskReddit Thread