14 People Share Their Awkward Crush Stories

©Max Pixel

How do you tell someone you like them? Do you wait for the natural conversation to occur so you can confirm the feeling is mutual, or do you dive right in with a not-so-subtle hint? These AskReddit users share the weirdest crushes scenarios they have ever been a part of.

1.  Intruder Alert

My cousin once had a crush on me.. She was 2 years younger and when I was 20, she saw something on a movie where the girl waits on a bed naked and waits for the guy to come in.. So when I was coming home (I live with my grandmother) she came to my grandma and she waited on the bed in only underwear, nothing on the top.. However, my grandmother failed to mention that I was bringing my college girlfriend for the weekend.. As I was unloading my grandmother offered to show the room that my girlfriend was going to sleep in. However, they opened the door to my cousin who screamed profusely.. Awkward..

2. All about looks

When I was around 14, a girl with a pretty severe physical deformity that resulted in bulging eyes and arms that didn’t really extend, started very obviously hitting on me, in front of all of my friends. I didn’t know what to do; she was a really nice girl but I was just not attracted to her at all. I quickly asked some other girl to be my girlfriend, and let her find out about that. She was upset.
I felt really bad, because due to her deformity I had seen her as a child, and I realized for the first time that she was my age and had the same teenage desires, and how I was just the first of a long line of guys who would reject her because of the way she was, and how it was just so unfair.
I don’t like thinking about this.


Friend’s mom used to get drunk when we were hanging out there and try and sleep with me.

4. Little black book

I was in high school, sitting in art class when this guy walks over. I didn’t particularly like him or not like him. I didn’t know him that well. He stops at my table and casually asks for my phone number. I say “Sure!” and he pulls out a piece of notebook paper filled with phone numbers…all suspiciously the numbers of nearly every girl in our grade. It was too late to say no and I got a phone call from him at least a dozen times a week for a month. The fact that no one ever picked up (save for the first time….boy was that an awkward phone conversation) never stopped him. I just pictured him calling down that list every day.

5. Spread Eagle

My best friend came out as gay and then proceeded to tell me how much he liked me. He knew I was straight, but decided it would be appropriate to straddle me whenever I sat down around him. Still waiting for it to stop.

6. “Stared at my house”

In eighth grade I was stalked for several months by a girl one year younger than me.
At first it was rather benign, we ate lunch together in our group of friends and hung out a few times after school. She seemed rather interesting if a little odd.
Then it started getting more creepy. She decided to read me some of her short stories which involved me tearing off her dress and raping her. I was called into the principal’s office because she decided to share one of them with her English class.
After that I decided I wanted nothing more to do with her but it just got worse. She started calling my home at all hours of the night and even stood in my front lawn from around midnight until 3 a few times. She just stared at my house. I can’t exaggerate how creepy it was.
She started writing hate mail to all my female friends saying they were c**ts etc and we got seriously worried she would do something to one girl in particular(this girl wasn’t actually one of my friends, she was just dating a boy with the same first name as me).
It all ended once I went to high school but she did the same thing to several other people before she was expelled. I don’t know what has happened to her since.

7. The Stalker

I had a stalker. Not even kidding, or well… as much as you can call someone a stalker in High School. I always treated my “stalker” with respect (Even though it was weird), she would follow me around school, give me these love letters, draw pictures of us together, make me these home made bracelets and necklaces, call me up at the most random times she even had my private email address. I tried to let her down easily multiple times but she didn’t give up. One time she appeared at my house crying, I had to take her in and stop her from crying. She would occasionally call up crying and I’d have to talk for hours on end to try and calm her down. One day I just had enough, so I told her as directly as possible (while still trying to be nice), “I’m sorry, but I’m not interested okay…?” She disappeared about a month later, moved country, school etc. Two years later she came back, I added her on Facebook and she told me she was sorry, talked to her a while and she seemed to have lost her craziness, she now has a boyfriend.