In high school, I caught a wickedly beautiful classmate sitting at my desk. When she looked up and saw me, she turned bright red and looked extremely embarrassed. Hours later, I realized that someone had written a love note directly on the cover of my notebook. . . And all I thought was “huh, that’s weird”. To this day, I think of how stupid I was at 16 u/InformalManager3359

I have very flexible joints. As a result, I was well known for doing tricks with my hands during my early uni days. Things like bending my fingers backwards to touch the back of my hand, touching my arm with my thumb, bending fingers into a Z shape etc. I was at a party with classmates and this girl I vaguely knew asked me for a private demonstration of my hands. I was slightly buzzed at the time so I said sure and took her to the kitchen while she giggled. I started doing my usual tricks but I quickly noticed something was wrong because she got this disappointed look on her face. She mumbled something akin to "ok cool" and left the party claiming she was tired, leaving me confused for the rest of the night. It took me 3 days of sobering up before I realized I had messed up and by the time I saw her again it was too awkward to talk about. u/Ralath1n

In college, my roommate’s gf was in town and I mentioned to a girl how I was going to have to leave the room. She tells me “my roommate is staying at a friend’s, you can stay with me.” I take her up on it. We get there and I go to sleep in the roommates bed. She asks what I’m doing and motions for me to get in her bed. I join her and proceed to talk about everything and anything until 5am when I say “welp, they’re probably asleep maybe I should go back to my room.” And I left. I realized the next day when she asked my roommate if I was weird. u/HamsterLarge4652

In highschool I asked a girl to come watch a movie rental with me and some friends. She was sitting on the floor in front of me, and rubbed her neck saying that her neck/shoulders were sore. Completely missing the cue to offer a back massage, I got up and offered her a Tylenol. My buddies ribbed me for that for a long time. Somehow with my terrible game I still managed to marry her and we have 3 kids now. u/twilling8

Went on a short road trip with a girl from work. When booking hotels for the stay, she said "Let's book a single room with separate beds; it'll save us money". I thought that was a good idea and went ahead. That evening when we went to bed, I was showing her a YouTube video on my phone and she went "Make yourself comfy! Why are you sitting on the edge of the bed?", and raised the comforter - indicating that I ought to slide in next to her in her bed (which I did). When we were chit chatting, I reached out for a bottle of water that was on a table across from her and accidentally brushed her bra strap with my elbow. I apologized and took a gulp of water. She asked "Is my bra in the way?". I said "Nah, I managed to get the bottle, don't worry about it!". One day after the road trip ended, it hit me. And yes, I know I'm an absolute dumbass. u/haajisquickvanish

This was back in high school. I was super shy. I had been crushing hard on this girl since freshman year and everybody knew it. She had thrown hints at me forever and I never acted. I was insanely good at math. So one day as I'm coming out of class she stops me and says that she heard that I'm some kind of math genius and asked me to tutor her. I asked her what she's going to pay me. She says very suggestively "oh don't worry, you'll be well rewarded". My stupid *** responds, no I need actual numbers to know if it's worth my time smh. I was so dumb lol. u/threat124

My brother was once driving a girl home when she said she thought he had a flat tire. She insisted they pull over and check. She directed him onto a narrow road surrounded by trees. He got out, checked it out and said it was fine. He was about to put the car in gear when she said "as long as we're here, let's just hang out a bit." He asked what she wanted to do. She said "I'm sure you'll think of something" and put her hand on his stomach. He chuckled and said "that tickles"...before removing her hand and adding "come over to my house, you can check out my Xbox!" Then he put the car in gear and drove home. u/_eviehalboro

My first weekend of college a girl asked me if I wanted to wrestle her in my dorm. I wrestled her in my dorm. Nothing more. u/Jdw5186

Met 2 girls at the club and we hit it off. After like 30min one of em says “wanna come with us to the car? We need to change?” What I said?! “Nah you guys look good.” Didn’t know anything was amiss until like 3mo later. I shot upright outta bed and realized my mistake. u/disphugginflip

I was on a night out with a group of college friends and we ended up meeting more people from our college whilst out at a club. We formed into one big group and I was introduced to a few new people who were friends of friends. One girl approached me and told me she had asked about me and found out we had the same name. I was kinda drunk and said something along the lines of “aw no way that’s so cool” and she said “yeah, and lucky for you I really enjoy moaning my own name.” And I just kinda “… :)” I was asked the next day by a mutual why I rejected her and then I had the lightbulb moment. u/BlueJuice_

So my boyfriend is so bad at flirting, we have known each other for 15 years and we were always just friends. We always had secret crushes on each other but we’re always dating other people. About 6 years ago after we had both been single a while, I had invited him over to go in the hot tub with me. Legit had candels lit and everything, not a move was made. Even after we got out I was sitting with him on the couch I put my head in his lap, he legit went nonverbal. The next week was new years and when the ball dropped I kissed him and all he could say was ‘you are interested in being more than friends?!’ Lol DUH That was 5 years ago, now we are getting married next year. u/Skrimppy666

In my junior year of high school I was a teachers assistant for a 12th grade AP English course, and sat near this gorgeous, smart, and really nice girl. We talked a lot and I liked her but always just thought she was way out of my league. About a week after our prom that year I was telling the teacher about how crappy it was because my date kinda ditched me. He said "well why didn't you ask ____?" When I told him how I never considered it he laughed at me and was like "Man, you've been missing a lot of easy signals. Don't worry, you'll get there." Cinner21

I worked as a bouncer 25ish years ago. One evening a slightly older and extremely attractive lady came back to the club and said that her car would not start. Eventually after chatting for about 15 minutes and just before closing I offered her a ride, out of sheer politeness and because I saw her tip bartenders really really well. When we got to her house she asked if I would like to get some water. I said okay and went into her house. After the glass of water she asked if I would not mind unbuttoning the top hook on the back of her blouse because she couldn't reach it. I did. Then I said thank you very much, have a good evening... and left. Never saw her again even though she was a fairly consistent customer until that evening. u/simple123mind

A girl I had a crush on sat on my lap because she had white shorts on and didn't want grass stains. She then sighed and said she wished someone would ask her to prom. I assured her that someone would. And it never occurred to me that I had a shot. Years later she punched me for being so oblivious. u/enigmaunbound

I was 19 and good looking back in '86 and I'd always be going on about movies. There were scads of older woman this office and one was constantly finding me alone and telling me that she'd love to see Blue Velvet but had nobody to watch it with. I told her it was kind of sensual, but a good thriller. She came back a week later and said her husband was going to be away if I still had the tape. u/The68Guns

While in high school I was at a gig with a bunch of people from my year and had been standing next to this girl the whole night chatting. Another guy asked us if we were together and she replied 'not yet' and I laughed and replied 'good one' while she looked at me weirdly. I had such a crush on her as well. u/McClernon

After a photo session with a close friend, she said I can stay the night when I said I'm tired. I obliged, thinking it's just a nice offer. During the night I woke up slightly because she had grabbed my hand, put it on her hip and pressed her cheeks against me. I was still groggy and didn't think much of it and went back to sleep. In the morning she turned around to face me, got her face so close her nose was touching mine... And again, I went back to sleep. u/krtshv

Not sure what I missed, but when leaving to go to bed at a staff conference, the lady next to me stood up and shouted, "I have been chatting to you all night, the least you could do is take me back to your room". Everyone heard it and she had magically disappeared from the course the next day. I am autistic and have been married for over ten yrs, so it was very unexpected - i figured she was just being super friendly u/boofing_evangelist

I really liked this nerdy dude in school and his friends had convinced him to throw a party when his parents were out of town for the weekend. We were in his room and I saw he had the extended versions of LotR. I had never seen them and he said I should definitely see them. I suggested a movie marathon the next day. His response: Oh, but you can just borrow them from me. I tried again and said (with a very flirty tone) that it would be more fun if we watched them together. That way we could just lay in bed all day. Him: Oh... so should I invite the others too? I gave up and figured I probably just misinterpreted his interest in me. Wasn't until a year later he found out what my intentions had been, when a mutual friend told him. u/nerdy-triceratops

This was back in college. Went to a talent show with a girl had a great time. We stop by a bar for a quick drink. It was a little past midnight. I walked her back to her apt she asked me "would you like to check out my place and have coffee" and I said "I am not a big fan of coffee. This was fun night, let do it again" As George Costanza said "Coffee is not coffee. Coffee is s**" u/nel_wo