I was a teenager in high school. Late 90’s. I had never really been on a date of any sort before, so this is a first first date story.

I met this girl online on AOL instant messenger. We chatted very frequently for a couple of weeks, then started talking over the phone almost every day. We were really hitting it off, so we started trying to figure out how to hangout together in person. Eventually, she invited me to come over to her house. I was stoked. She said she lived in a nearby suburb, and relayed some directions to me, which I wrote down on a piece of paper. It didn’t seem too far. She said her parents would be home, so my parents said it was ok for me to go over there. I mean, they were probably stoked I wanted to go see a girl too, as I’m pretty sure they were starting to think I was gay by then. I wasn’t, but that’s a separate messed-up story.

An issue came up, though. Her parents said she couldn’t hang out unless she cleaned her room, as it was really messy. I said “No problem! I’ll help you clean it and we can hang out after!” Genius, right?

Anyway, hormones firing on all 8 cylinders, I hop in the car and begin my journey. Turns out she didn’t really live in the city she said she did. That was just the nearest city to where she lived. I’m driving, driving, driving, further away from town thinking I’m lost, but I’m not. I remember turning around and doubling back a few times assuming I MUST have missed a turn. I did not yet own a cell phone to call and verify with her. Folks, the struggle was real back then, LOL. I just eventually followed the instructions as best I could, and eventually found my way. They were not good instructions. It was a miracle, really.

I go up, knock on the door. She and her parents answer the door and let me in. These parents were weird. They were basically gushing to meet me and let me in, but were strangely stoic at the same time, if that makes any sense whatsoever. Whatever. But then, all of a sudden , these parents that were going to be there while we hung out suddenly grabbed all of their things and bounced. Drove off. Huh, weird. They just left this strange boy they’ve never met and their daughter alone in their house. Good thing I’m not a creep, I guess?

This girl is grinning happy, but then gives a warning. She says her room is really messy. I say “It’s ok! My room gets messy sometimes, too! Let’s just attack it real quick and then we can hang out.”

Narrator: No, the boy did not actually know what a real messy room was.

We go in her room and I am shocked. I try not to show it, but it’s bad. Really bad. Every surface in the room is covered with stuff. No part of her floor is visible. Just clothes, toys, books, all sorts of stuff covering the floor, the bed, the shelves, the dressers. I take a moment to look around and take it all in. I’m already here. I’ve already agreed to help her with this, and I really want to get to the hanging out part. I clap my hands and say “Welp! Let’s grab some trash bags!”

So I spend the next couple of hours at least helping straighten out this disaster zone. Now, you really get to know a person when you dig through all of their stuff. There were a couple of things of note. First, it became apparent that this had never been done. Ever. As we pulled up the strata of clothing and toys on the floor, it was like an archaeological dig. The further we got down, the smaller the clothing became. The toys looked like those of a child younger and younger. By the time we got to the bottom, there was toddler clothing. Once able to get under the bed, there were baby toys under there.

At one point, I found a bible, and asked where she wanted to put it. Her eyes widened and she got very serious and placed it up on one of her shelves with the cover facing outward, on display. The manner in which she did this was a little creepy. Now, I was religious and had recently finished up Catechism at that point, so being happy to find your bible didn’t seem weird to me, but I found her a bit dramatic. Whatever. I keep going, and then I find a witchcraft book. SAME reaction. Eyes wide, she places it up next to the Bible. She then turns to me and says, “You know, sometimes, I feel like I’m a bit closer to the devil.”

Like an oblivious character in a horror movie, I don’t get too freaked out. I’m like, dang, this girl is weird and has some issues or something. She starts talking about sex. Saying something along the lines of how she’s had it before, and wondering if I have or not. A lot of things were said by her that, out of context, may have been just a bit quirky. All together like that in that setting, though, I really wondered what was going on with this girl.

Eventually, we finished the cleaning. Many bags of trash and old clothes and toys all bagged up. Vacuumed, dusted, bed made. It felt so good and clean and open. A sense of self satisfaction. She sits down on the bed with a weird look on her face. Looking down at the floor. I say, “Alright! Now we get to actually hang out! What would you like to do?”

Her parents walk in the front door. She slaps her knees and says “Welp! It was nice hanging out! My parents said I could hang out until [this time], so you’ll have to go home now. Maybe we can hang out again soon!”

Narrator: They would not.

On my way out, I look around at the house once more. It seems normal. Clean. Very clean, even.

We didn’t really chat anymore after that. I actually tried to, mainly out of curiosity and concern. I had questions at this point, as you would imagine. She no longer had interest in responding. I just hope she appreciated having her room be comfortable.

Definitely not as bad as some of the others mentioned here, but when I was 18 a slightly older coworker who had a crush on me for a while asked me out. I said yes because I didn’t really know how to say no at the time. I wasn’t physically attracted to him, but he was a really nice guy and I didn’t see the harm in giving him a chance.

We’d already worked together for about a year then, so he knew a few things about my interests. He wanted to plan the whole thing and surprise me with where we’d go. We agreed for him to pick me up from my house at noon. I thought, “great, lunch date”; they’re pretty chill/non-intimate.

So the day comes, he picks me up and we start driving. He tells me he’s taking me to the natural history museum. In DC. Over an hour away. Far for a first date, but I love that museum so I go along with it.

We get there, wander around, chat, and after a couple hours walk out onto the national mall to some random food truck, grabbing a nearby bench to people watch while we ate. I wasn’t feeling a connection, however, was patient and respectful, after all, we had a good enough time so far, and he put effort into planning this.

Now, normally, after the meal/activity is complete this is when a day date starts to come to a natural end. At this point it’s past 4pm, so I suggest we head to the car, thinking to myself that it’s a long drive back. Surprise! He tells me he got us two tickets for DC United that evening. Not a huge sports watching fan, I didn’t know how to react. Being young, inexperienced, and afraid to upset him I feigned excitement.

He drove us to the stadium, parked, then got out to get something from his trunk. Another surprise! A cooler of Smirnoff ice. After the weirdest tailgate we go into the stadium, watch the game, get hotdogs, and the whole time I’m dreading what other surprises he has in store. He seemed so normal before.

Luckily, after the game he finally took me home. I don’t remember what time it was, probably around 9pm, I just remember feeling relief at the sight of my front door. He tried to kiss me when dropping me off, but I managed to avoid any physical interaction. Looking back, it was the weirdest, cringiest date, and the main reason I always drove myself to dates from then on.

I’m a leftist dude living in one of the most leftist cities in a generally leftist and progressive country (although partly less so at the moment…) so generally have no issues with different political views and morals, most people are nice.

I matched with a girl on a dating app only for vegans because I was tired of having to ask about it, deal with having an omnivore partner and of having idiots match with me only to be assholes towards me from mentioning it in my bio.
We texted for about a week and got along super well, she was very into me and was the first to ask for a date so we set one up.
The date started great too, we really clicked and I thought she was one of the most beautiful humans I’d ever seen. Then as we’re about to finish our food and pay the bill she tells me that I need to pay for it, I ask why (I happily would have, but was just interested in the reason) and she tells me that since I’m male I need to “atone” for all the bad shit men has done to women throughout human history… I thought she was joking but she really wasn’t. I was so floored that I didn’t know what to say so I just said nothing, I paid for my food and just left.
I wrote with her a few times after that out of morbid curiosity and asked more about her political views etc. and it wasn’t good. She was not a feminist in my view, she was a man-hater and a militant extreme leftist with many morally fucked up views.

I’m just glad I found this out on the first date and dodged a bullet.

Asked a girl out on a date. She invited me over to watch a movie with her at her parents house (we were in our late teens). I arrived; her recently deceased family dog and incredibly distressed mother were both in the kitchen. Dog was a really big golden retriever that had been euthanized, and the mom had bought him home? Not sure why? Maybe to bury in the back yard or something? Idk

Anyway I offered to leave but she was insistent that we watch the movie together, which we did, on the couch, with her mom crying in the next room. Halfway through the movie the mom screams he’s still alive, he’s still alive. Go into the kitchen, she’d gone to move the body and it had expelled air and made some noise. I had to explain, with my best year 12 biology, what had happened. Five minutes of this woman losing her shit with grief out of her beloved companion dying.

Girl insisted we watch the last 10 minutes of the movie, it finishes with us watching in silence, I get up to leave and said something stupid like hey I’d love to do this again sometime and she says “I have a boyfriend”

I’m like alright well that’s that then and didn’t put in any more effort. Stupid me, she was hot and I really liked her. Being a dipshit I wrote a song about it, using the three guitar chords I knew, which takes me to act ii…

…five years later, I’m at a party, exchanging worst first date stories with friends and fellow partygoers including a cute blonde. I wait my turn, tell the story, she laughs her arse off and then goads me into singing the song, accompanying myself poorly on the guitar. I absolutely fucking nail it, everyone is in stitches, sit down next to her and the night goes from there. We end up leaving the party for a walk down to the local beach, made out on the beach, things get frisky, jump in a cab back to my house, in bed together, have drunken sex…which results in a broken condom. She lives literally the other side of town so we have to wait till (a) I’m sober enough to drive and (b) pharmacy is open to get a plan b, then have the most awkward drive back to her house. Get there, offer to walk her to the door, she says no, kisses me goodbye in the car, then texts me…to say she has a boyfriend.

I worked a security gig where I had to call into a phone call center every hour to show I was awake. I was there for three day and got to know the girl on the other end pretty well. We ended up almost talking the entire last night.

We made arrangements to meet after we both got off work. I was incredibly nervous and my face had gotten itchy and i scratched it so badly my face swelled up. I had no way to get ahold of her to postpone our meet up. So we met and she freaked out at the sight of me and left. Never saw her again after that.

We went to walmart for her to buy fem-hy while telling me about her baby’s daddy freeloading in her home.

I said I had never eaten vegan food. She asked if I’d like to try it at her favorite restaurant. She then made a huge deal about me being “only” vegetarian as we ate. Stunned as she went on and on about what a terrible, ignorant person I was, I noticed there was something odd about her front teeth, like they were stained. I didn’t think much of it and tried not to stare. She also kept insisting repeatedly that it wasn’t a date. Ok, that’s fine, I said which only seemed to make her angrier.

We get in the car, and I’m relieved it’s almost over. She looks in the rear view, and starts freaking out that I hadn’t told her she had lipstick on her teeth the entire time. I tried to explain I didn’t know what it was and didn’t want her to be self-conscious. Awkward silence as she drove me home. Next day I noticed she had blocked me on everything. Good riddance I guess.

October 7th, 1999. Was a miserable date. Early snow. Sucked.

Met a woman on OKCupid back in like 2014. We seemed to hit it off, so we agreed to a mall date since we were both broke (she was a college student, I was a youngster in the military). We were gonna get food and just kinda walk around and window shop and talk. Gonna try to keep this short, but a lot happened:

1. Had me pick her up from her dorm, went up to the dorm, her roommates were drinking even though everyone was underage, and they’re thanking her for having mom get it for her. She’s super nice about it, but proceeds to complain the entire drive and start getting emotional because she hates that they drink when they’re underage, etc. Yet… She provides it…

2. She doesn’t eat when we get to the mall, and instead spends the whole time I’m eating, talking. No breaks for me to respond, just keeps going.

3. We start walking around the mall, and she starts randomly pinching me. Like, painfully, randomly pinching me in my arms and torso. I’m finally like wtf is with the pinching, and she says that she was doing it because I wasn’t holding her hand while we walked around… We just met, and the vibe is already pretty crap, and how in any way is that a way to communicate…

4. We finally leave and get back to her dorm, I walk her to her door, and I’m invited in by her/the roommates. Fine, I decline drinking because I’m a good sailor, but my date and I exchange some pleasantries with the roommates and then head to her room. It’s basically just a bed, I think maybe she was just super nervous at the mall and being in her own environment she’ll relax.

5. We’re just chatting, and the pinching starts again, and she’s kinda just going for it with no breaks. I’m getting pissed and finally grab her wrists and tell her to stop, and she bit me. On the chest, like, hard, not a romantic playful lil love bite. I’m, again, taken aback and am like, wtf?!?

6. She starts giggling and tells me that that’s how women tell guys that want to make out/get intimate. What?! No, not how that works, at all… Especially not on a first date. But, fine, I tell her she can just ask, figuring she just wants to make out.

7. After a little while making out, the pinching starts again, and apparently this time it’s how women say they want to have sex. I wasn’t so turned off, it just didn’t happen, like, at all.

8. She walked me back to my car, and I drove her back to her buildings door, and she bursts into tears about her roommates and the drinking again, I console her enough for her to feel better and go back to her room. Say goodnight, and she just sits there staring at me. I’m kinda done at this point and just ask what, and I get, “No kiss?” Fine…

9. Get a text while I’m driving home telling me it was one of the best dates of her life, she really hopes we can see each other again soon, she really liked me and was attracted to me, etc. I respectfully declined, and when she wouldn’t just take that as an answer, I sent her a text essay outlining basically all of the above, and I honestly can’t remember if she responded.

Honestly, she wasn’t a bad person, and maybe at different stages in our lives things could’ve gone better… But she had a lot going on and a lot of life to live and learn from, and I wasn’t up for the ride. Hope she’s doing well, if she sees this and recognizes it, and that she stopped using pinching as a means of communication.

Oh, and to illustrate how hard the pinching/bite were, I had dime sized bruises all over my arms and torso the next day, and a bite mark bruise on my chest.

I got stood up at the restaurant. This was back before online dating was the norm rather than the exception. It sucked, but I learned to get over that kinda thing.

A friend persuaded me to go on a date with a girl I wasn’t particularly into. We went for a meal, then she wanted to go clubbing. But I’m not into that either, so she broke down in tears. I was pretty sure I hadn’t said anything that bad, but then the story came out: her ex-partner had the same first name and job as me, and the meal and clubbing were his favourite things, but he’d been found dead in another country with his common law wife and kids, and the similarity to me was effectively his coming back from the dead to be with her again.

No there wasn’t a second date. I haven’t seen her since either. Neither have I taken dating advice off that friend since, although we are still friends.

Stuff like these stories terrifies me from ever dating, even though I feel the sadness of being alone more and more. And I’m on my mid 30s but I just can’t imagine being in more awkward situations than the ones I’m already forced to be.

I took my current gf and my parents to a nice restaurant last night. She mentioned she’d only been there once before, on a date, and that the only reason they went to that restaurant (very $$$) is because he had a gift card and was going to cover the meal. Orders all kinds of expensive stuff. The bill comes and then supposedly he realizes his gift card, if it actually existed in the first place, was for a different restaurant. She ended up having to pay on her CC because he had no other forms of payment. Obviously didn’t work out for him in the end.

First date with a girl: I open the car door for her when I pick her up. As she gets in, she hooks a hoop earing on the corner of the door and rips it out of her ear. The next 6 hours are getting her through ER to get stitched up.

Funny enough, I did get a second date and we hung out for about a year after that.

We met at a café for coffee and pastries. He talked about himself non-stop, I couldn’t even get a word in, like not even to ask follow-up questions. Every so often he would realize what he was doing and then pause and sat “Oh, uh, how about you?” as though he finally remembered I was there. I could get about 2 sentences in before he took over the conversation again.

After the first date I was willing to give him a second chance because I know people can talk alot if they’re nervous, so we called each other a few times, but it was the same thing, just him talking the whole time. He would call me after work and ramble for an hour about nothing. I finally broke it off because he just never shut up.