Hold onto your butt’s for these. I have two that were equally awful.

I had a date with a guy I met on a dating site. His profile picture was of him standing way back in the background, so I couldn’t see what he looks like. But what the hell, he asked and I said yes.

He asked me out to IHOP at 9pm which is an unusual choice, but sure ok. I showed up a little early and sat at one of the booths. This guy walks in looking absolutely absurd. He’s wearing a fedora, a tacky animal print tshirt that’s way too large, tons of jewelry on his wrists/neck/fingers, cargo shorts, an attempt at a beard, and sandals with socks.

Not going great, but maybe he’s a nice guy with no sense for fashion. I’ll give him a shot.

We greet, he sits down, and with a raspy smoker voice, he begins to explain each and every piece of jewelry and what magical properties they bestow upon him. This one wards off evil spirits, this one wards off wraiths and phantoms, this one gives me the power to read emotions, this one allows me to talk to god, and on and on.

Clearly they weren’t working as I was very uncomfortable at this point. A man of his age dressing like that, being superstitious, and believing in magic? So very many red flags. I decided I never want to meet him again, but I was determined to finish the date on a positive note.

But then his ex-friends came into the IHOP, and shit went south quickly. They began to argue and shout at each another. Apparently my date was kicked out of their Pagan religion group… thing? My date was really bitter about it and decided to bring a date to this specific IHOP at this specific location and time because he knew his ex Pagan group regularly meets there. I think he was trying to prove something by having me there, but I don’t know what.

I paid for my half of the meal and slipped away. My date never noticed that I left. If his ex-Pagan group noticed, they didn’t say anything.

My second equally bad date was meeting another guy on the same dating site. He was an ok looking guy, 5 out of 10. But then again, I’m no beauty queen either so ehh, why not.

We were going to the movies for our first date, but we arrived suspiciously too early. He said he got the movie time mixed up, but we can pass the time walking around in the Petsmart store nearby. You clever clever man, that’s exactly how to melt my heart. Kudos to his plan.

We walked around the pet store, looking at all the cute animals, then we went to go see the movie. I don’t know why, but he refused to sit next to me. He insisted on keeping an empty seat between us. We ended the night and went our separate ways.

He called me again, inviting me to his Dungeons & Drafons game, which of course I said yes. Hell yes! But as it turns out, he had absolutely no interest in dating me. All he wanted was a female to join his game and play certain NPC roles in his campaign.

I’m ashamed to say I did the voice acting for his NPCs. After that, I never heard from the guy again.

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.

The only time i tried online dating apps to the point of actually talking to another human i met a young woman and we exchanged a few messages then arranged a phone call. On the phone she wouldn’t stop talking. It was pretty amazing, this flood of words pouring from her. I supposed it was because she was nervous, but still - being pretty pessimistic about the whole online dating thing to begin with - figured this would never work out because her non-stop talking was starting to weird me out a little. Not in a terrible way, just a little.

Anyway, she was going on and on about her job but was carefully avoiding any details that might identify where she worked, i guess so as to stay safe by not revealing too many personal details to a stranger. Somehow, though, I figured it out. She told me what area of the city she lived in, and i got enough details about the kind of work she did that i said something like: “Oh, you work at the Goodwill on blahblah street” and then there was dead silence. The flood of words stopped. We hung up soon after that. I felt really cool about guessing her workplace, like a detective, thinking i’d impressed her with my mind, but it wasn’t until years later that it dawned on me that i’d weirded her out even more than she weirded me out. A double oblivious weird out.

I’ve been catfished no less than three separate times.

Each one would post pictures of themselves that were either from when they were much younger, or in heavily contorted positions that hid their true proportions. I’m a very in-shape guy, and want my partner to be able to do things like hike/bike long distances with me, go climbing, outdoorsy stuff that I really enjoy.

Each one I felt like I had a connection with, but the fact that they concealed this was ultimately what lead me to break things off (in an amicable but forthright manner - “I like you but you misled me with your pictures, and that’s not how a good relationship starts.”).

But one had an extra flavor to it that makes it one of the worst.

Met this girl on tinder, we hit it off, she tells me she’s a cam model and I’m like “whatever you gotta do to make that money,” because I don’t judge, and the pictures she was sending me were tastefully erotic and nothing too graphic. Think softcore porn with some bondage and cosplay. Anyway, we meet at a restaurant and she’s wearing this big baggy raincoat, and I can tell immediately that the pictures she was sending me were pretty old. Her hair was a different color, different length (I love short dark hair on a woman), and she’s at least 50lbs heavier. However I’m of a mind that even if a date doesn’t end in a relationship, you can still have fun and perhaps make a new friend, so I just go with it.

We were there initially just to chat over drinks, but she orders an appetizer, a heavy entree (a pasta dish), AND a burger with fries. I helped eat the appetizer so she wouldn’t feel like she was eating alone, but I wasn’t hungry so that was it. It went OK, but halfway through the meal I realize I left my wallet at home, so I couldn’t pay. I end up buying a giftcard for the restaurant through a phone app in an attempt to at least pay for my portion of the meal, but the employees just could not care less, and she ends up covering it. I feel bad.

Now she invites me back to her place, and I feel obligated to go. We get to her apartment, and who opens the door? her mom. In a nightgown, smoking a cigarette. Keep in mind this woman is at least 33.

Her mom goes outside to smoke on the porch while she leads me to her bedroom (while grabbing a bottle of whisky). it’s the most disgusting bedroom I’d ever seen. Like, you could not see the floor for all the dirt and various debris. She pushes a pile of mostly clothes off the bed, and she invites me to lay down and watch TV with her. This is when she tells me that she’s gained weight because she recently broke her spine doing god-knows-what, and that she’s been recovering for almost a year now. She takes a slug of whiskey and takes down my pants, proceeding to contort her spine into a terrible position trying to give me a BJ. I couldn’t maintain an erection because of how worried I was about her spine, so I just kind of stopped her, got up, and left. Her mom waved to me from the porch as I walked out.

Another horrible date where I wasn’t catfished-

Met girl on Tinder, she’s super into me, to the point where I think she might have nefarious intentions. Like, we started talking and THAT night she wants to meet up. Red flags. She tells me she not only wants to hang out that night, but she wants to hang out AT MY PLACE. Another red flag. Then she tells me that she can’t drive to me because she doesn’t have a car. So her sister will drop her off at a parking lot where I can pick her up. I was letting my horny-ness dictate my decisions that evening for sure. I pick her up, and let her sister take a picture of my drivers license so she can rest easier.

She hops into my truck and we’re headed back to my place. She whips out a bowl, packs it full of weed and starts hitting that thing like a champ, two hits and it’s gone. She doesn’t offer me any, but she does inform me that she’s on mushrooms and can have some of those if I want. I decline.

We get to my house, and we’re hanging out in the kitchen talking. I put on background music (lofi hip hop beats to study and relax to lol) but for whatever reason she decides that it isn’t enough, and is streaming spotify on her phone, she informs me that she has 5 kids from 2 or 3 different dudes. She smokes like 3 more bowls from her chillum before inviting me to my own bedroom. We have sex, and at the moment of her climax, she yells to stick my thumb up her butt, it was dark and I couldn’t find it quick enough/hesitated to just shove it in there, and she seems very displeased. I tell her that I need to work early in the morning, and ask if I’ll be able to meet her sister in the same parking lot (it was on the way to work). She doesn’t really answer, but we turn in for the night. I offer her a new toothbrush so she can clean up before bed, she declines.

In the morning she asks for something warm to wear, and I lend her my favorite hoodie. She says we can have sex again, but only if she’s my girlfriend, I decline. Then she tells me that her sister can’t pick her up, and I’ll have to drive her to her sisters house (where she’s staying with her 5 children). This house is an hour away. When we arrive I thank her for the evening, and make sure to get my hoodie back. I’m very late for work, but luckily nobody cares. I told her the next day I wasn’t ready to be a father figure, and left it at that.

Just realizing we were on different pages made it pretty bad. I went into it thinking we were on a real date and meeting for dinner and getting to know one another. He thought this was a lot more of a casual encounter…

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.

Dude tried to rape me. Might be his worst date too because he left with multiple broken fingers and a broken nose. It could have been better for me / worse for him if the cops took it seriously, but the fact that I fought back and he wasn’t actually successful in raping me was enough for the cops to wave it away as a domestic dispute that self-resolved when I left.

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.

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.

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.

five minutes after meeting her, she went into a graphically detailed spiel about how her father sexually abused her as a child. and she was very upbeat, happy, and smiling as if it was a delightfully fond memory the entire time.

I dont know what the end of the story is because by the time she got about, what i hope, was a quarter of the tway through, I had already been so completely creeped and skeezed out that I had developed a cold sweat, and I just got up from the table, said nope, and walked away.

I was kinda fucked up for a short while afterwards.

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 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.

I had one where she obviously wasn’t actually interested and just came for the free food cause she was poor. I hung out for a bit, bought her an extra meal to go and then just left.

Probably the first one I ever had.

Because my parents were there, too. 😩