I was at a pool party and, in typical pool party fashion, nobody was in the pool. A cute girl asked me if I wanted to swim and I said, ‘Eh looks like nobody’s out there.’ Some time passed and people started leaving and she asked me AGAIN. I said, ‘Eh looks like people are leaving.’

I used to work with this hot blonde chick who had a really shitty boyfriend. I was also in a shitty relationship and I fancied her hard. Figured she was way out of my league. We were in a group of friends who used to hang out, and one Friday she asked me whether I wanted to go out. She picked me up, looking good. When we got to the bar, I start drinking (not too much), and we talked. When we leave she asked me if I wanted to go somewhere. Me, like an idiot, said sure, and with her not being local to my area, I proceeded to take her on a shitty tour. When she got bored of this, she dropped me home. The look of disappointment in her eyes when she dropped me home will haunt my dreams forever. It was literally years before I realized she wanted to go somewhere quiet and have her way with me. Maria, you were so hot, and I was a totally oblivious idiot.

A friend of mine helped me clean my room. When we were done, she sat down on the bed. I didn’t think she was interested, not even when she laid back and asked what we wanted to do now. I offered her a coffee and brought her home. When I returned to my house and went up to my room, I noticed that she left a bag behind. Curious, I peeked into it and what did I find? Clothes and underwear, as if for a sleep over.

Had a friend come over for hanging out, drinking beers, adult sleepovers. one day she basically insists I touch her tits to feel how firm they were, like I didn't believe how crazy firm they were. Well, I can tell you I kinda poked/booped it because I was a social idiot who couldn’t understand what she was letting me do. I just thought it was neat how firm they actually were.

I went on a date with a beautiful woman when I was 21. She was a few years older than me and I felt a little intimidated. We had a great date, went to dinner and a basketball game. When I took her home after the game, she asked me in for coffee. I told her that I ‘didn’t like to drink coffee this late’ and that I ‘had to get up early the next morning.’

I was in New York in the backseat of a taxi with this woman I met at a hostel. We’d known each other for a few weeks and she was always quite flirtatious, but I presumed that was just her personality. We were both pretty drunk and she started caressing my leg and resting her head on my shoulder. What happened next I still can’t explain…I really have no idea why I said this, but I said, ‘You really remind me of my sister.’ Yeah, that was the end of that.

I was on the patio outside of a bar talking to this guy when a bus passed with an advert for the new Tomb Raider game. The conversation turned to the game and I said that I bought it on the release date. Next thing he says is, ‘I should come by one night to play it.’ I responded that it was a single player game. I didn’t realize until the next day what he was saying.

There was this girl in high school who would rub against me, hug me, tell me to grab her ass, etc. Being dumb, I thought she was just being nice. It wasn’t until after high school that I realized how dumb I was.

I was a weird, chubby teenager who worked at White Castle and there was a super-cute girl that also worked there who I got along with really well. On my day off, she asked if I wanted to pick her up after work and hang out. We were talking and she showed me her room, then said she needed to change. She told me I didn’t need to leave, just turn around. I did, then she said she was just kidding and I didn’t need to turn around. I stayed turned around and she eventually changed. I still cringe hard at that memory.

I was online dating a woman for about a month that I had bonded with over a shared love of nerdy stuff. She and I were texting when she sent me a video of her saying she was going to a local bar for a drink. I decided to get dressed and meet her there. She’s funny, gorgeous, and smart, so I assume she’s way out of my league. I was in High School at the time and attended an English course in a language school nearby. I got along well with the class though I was younger than them by 2 years. One day, I was discussing my summer plans with a girl and I mentioned I would like to go to a one-day music festival 3 hours away from our city but didn’t have a car to go and come back. She ever so kindly mentioned that she also really wanted to go there but had no one else to go with. She continued by suggesting we should go together: “We can go in my car and if it gets late we can sleep in it. I thanked her but declined because my parents would probably not like the idea. Yup.

My best friend told me that she ‘gives amazing blowjobs’ while trying to snake into my pants, but my thick ass responded with ‘cool,’ thereby preserving my virginity for two more years.

So I was meeting up with a girl from tinder, nothing unusual so we go for a walk and had a great talk. It gets late and we are sitting on a park bench and out of the blue she tells me when somebody in her country (she was on vacation) blows cigarette smoke into your face they want to fuck you. 5 seconds later she blows smoke into my face. Me, an intellectual, thinks how rude of her to do that. On my way home it finally got to me. I’m a dumb shithead.

I went on a date with a girl leagues hotter than me. She invited me over and my dumb brain didn’t pick up on her complaining about a backache meaning ‘massage me.’ She then invited me to sleep in bed with her and I thought, ‘oh well, I don’t want to be ungentlemanly and presume.’ She stopped texting me after that.

In college, a girl asked me to ‘come over and help move a bed’…I brought a friend along to help.

I was once at a party that was like 90% girls. We were at my friend’s parents’ house (while they were out) and there was literally just one other guy there besides me. A few of the girls got into the hot-tub and all beckoned me in, but I refused, stating ‘I don’t have any swimming gear.'”