In theory, dating is really exciting. Who doesn't love the thrill of getting to know someone who could potentially be a great match? Unfortunately, the reality is that while dating can be exhilarating, it can also be really, really dreadful because of how many weirdos there are out there. These Redditors know first hand how weird dates can get. Read on to find out what happened on their strangest dates ever.
Content has been edited for clarity.
The Craigslist Challenge
“So, a few years back, I lost a bet with a friend. The loser had to go on 10 Craigslist dates. Here’s one of them.
The rules were as follows: I had to post a personal ad in the women seeking men. The ad had to be simple. I had to correspond with the people who responded and if they asked me out on a date I could not refuse (up to 10 people). Once the ten was met, I was off the hook.
I don’t remember the exact wording of the personal ad, but it said something along the lines of ‘young, professional woman seeking young professional man for light conversation and friendship.’ Enter the crazy.
So first date was with the first man who responded within two minutes of the ad being posted (yikes). He responded saying he had just moved to the area, was 29, and worked as a lawyer. He too was looking for friendship and to meet people in the area. We exchanged emails back and forth, and in the third or fourth email, he asked if I would like to meet for coffee. According to the rules, I had to accept. So, I set the meet up with him at my local coffee bar. I asked to exchange pics so we knew what we looked like, but he evaded and instead described his clothing.
I went to the meet up accompanied by a close guy friend who works as a bouncer. He sat a few tables away for support and in case things got crazy. I drank my coffee and waited. I told him I would be wearing a red cardigan and he said he would be wearing a blue button down. Before I knew it, an older gentlemen (late fifties, early sixties) sat down at my table asking me if I was the girl from the Craigslist ad. I confirmed I was and he introduced himself as the man I was supposed to meet.
I immediately called him out on lying about his age to which he replied, ‘Well in my head and in my heart, I’m 29, so what’s the difference?’
Yeah…he then continued on to admit he was not a lawyer and that he was a retired sanitation worker. I asked him why so many lies? His response, ‘I always wanted to be a lawyer and you said you wanted a professional, so I figured it was a good match.’ He started getting upset that I was asking him so many questions and that I was implying that he was liar.
At that point I asked him point blank, ‘What were you expecting from this? What did you think would happen when I met you and realized you lied about everything you told me?’
He responded, ‘We had so much in common, I just thought you were already in love with me and you wouldn’t care.’
I was speechless. I didn’t even want to know how he had the idea I was in love with him. I was starting to get super uncomfortable.
I looked over to my friend and implored him to save me, but he didn’t notice my distress at first. The gentlemen saw my distress and smiled while he asked me, ‘Are you uncomfortable?’ He started leaning over the table as if to grab my hand, but instead grabbed my coffee and started chugging it while making direct eye contact with me. I sat there stunned and unsure of how to react. I looked over at my friend again, and thank God he saw my look that time. He immediately came over and pretended to be a friend who happened to be at the cafe.
I stood up to greet him and after a moment of chatting, made an excuse to use the bathroom. My friend caught the drift, and as I went to the bathroom, I booked it out first and he quickly followed.
Thus, ended my first Craigslist date in all its weird and uncomfortable glory.”
Used As A Meal Ticket
“This is back in the prehistoric era known as the mid 1990’s when I was 19. I met a cute redhead at a party and instantly asked her out. So we go out to dinner, her pick, and she chooses Marie Callender’s. The restaurant, not the frozen food. The entire time we are there, there was nothing but silence. However, she orders a huge meal. I’m thinking she has the metabolism of a race horse to be that skinny and eat so much food.
Our meal shows up and she goes down on the pot roast like a savage and in between bites she regales me with how she lost her job and is living in a rundown house that has a leaky roof, the powers been turned off. Oh and she and her LESBIAN girlfriend have been starving (her emphasis not mine).
With that revelation, I’m struck speechless and don’t really know what to do. She has her leftovers boxed up (plenty for her girlfriend) and dashes before the bill is even presented to me. At least we were too young to drink.
Some friends confirmed her story and I was the butt of some jokes for awhile. Even at the time, I found the whole thing surreal and hilarious. At least shortly afterwards.”
“Oh That’s Just My Fiancée!”
“About five years ago, I had just moved to London and met this guy on a dating website. He was generally not my type. Still, I was fresh out of a long-term, damaging relationship and trying to meet new people.
Fast forward to the date. He takes a call from a girl and he says to her, ‘Oh, I’m just in the pub with (male roommate’s name).’ I can hear her on the other end getting worked up about something and him telling her to calm down. The alarm bells already start ringing.
He hangs up the phone and says, ‘That was my fiancée, but not a real one. Just one I’m with for her visa.’
At this point, I’m already thinking ‘forget this.’
He continued on with his excuse, ‘She also lives with me…’ in his two-bed apartment with this other roommate. Cozy.
‘Oh yeah, I should probably tell you: I’m getting married in three weeks.’
At this exact point, I just said, ‘Well, I’m going home,’ and start putting on my coat.
His reply was even more classic: ‘Do you want to help me buy groceries first?'”
Their Second Date Will Be When Pigs Fly
“I met a girl online and we talked it up. While she seemed a bit immature, I thought heck, why not? She casually mentioned she really liked pigs. What she meant to say was she was obsessed with pigs. OBSESSED.
We go to one of the best restaurants in the area for a first date (bad idea). Sometimes pictures are from someone 10 years prior, or the person hides things, etc. But that wasn’t the problem. She looked just like her pictures, but I didn’t even have to have seen her first, because everything else about her gave it away.
She came in a giant T-shirt that had a sparkly pink pig on it. Earrings? Pig earrings. Bracelets? Yep, pig bracelets. I swear her dad might have been Homer Simpson. She had this headband on with a little pig on it. Her shoes? Yep, pigs on the front of the toes! But best of all? She had a GIANT (or at least it seemed giant) pink purse with the face of a pig on it.
You could not stop seeing it once you did. And I’m sure everyone else in this nicer/classier restaurant saw it too. I felt overdressed with her, but under-dressed with every other couple there. It was beyond embarrassing. For some reason, which I have to convince myself was politeness not stupidity, we still had dinner. But folks, it was the fastest freaking dinner I’ve ever had at a sit down place.
I practically blurted out something about how, ‘Oh, you really do like pigs…’ which she started giggling (oinking?) and going on about how everything she has is pig themed. Then she wouldn’t stop, and it became the dominant part of the conversation. There were a dozen other things that made it a train-wreck, but these were the clinchers to a solid 0/5 date. I remember afterwards confiding in a friend of a friend because I had to tell someone; and then I promptly buried this as my worst date.
That Was No Accident
“I went for a meal with this girl I met through a dating app and it was going really well. We started talking about movies and then we decided to go to the cinema to go watch Inception. She said there was a cinema nearby, but I didn’t know the area at all, so I used the GPS on my phone and she held it and directed me.
Once we got there, we started walking inside and I realized I didn’t have my phone in my pocket. I said I must have left it in the car and started to walk back to get it. She was trying to get me to leave it and saying we would miss the film, but the phone was only about a week old so I was really paranoid about it.
We checked the car for about 10 minutes but we couldn’t find it. I asked her to check her jacket and her bag but she said it wasn’t there. A couple parked next to us so I asked them to ring my number because I couldn’t find it. It started to ring and it was obviously coming from my date’s handbag. She took it out and said she must have missed it.
I thanked the couple and locked my car and as I turned back around, she was walking the other way. I ran to catch up and asked what was going on, but she was very dismissive and was barely talking. That’s when I realized it wasn’t an accident and just left her to walk home alone.
It didn’t occur to me until years later that she could have done this with other people. I really regret not reporting her.”
“Spinsterhood Is More My Jam”
“I met a guy online (of course) and after talking for a couple weeks we decide to go out. I meet him at his house because (supposedly) his car broke down that morning. This guy is dressed like an extra greasy version of the Fonz. I try to look past this, but secretly I’m devising ways I can destroy his leather jacket and dispose of his pomade. His house was also filthy. If you know someone is coming to your house for the first time, maybe consider wiping down the counters and chucking the old pizza boxes.
While eating dinner, he never once asks me anything about myself. He rambled on for at least an hour about his job as a customer service representative, repeatedly comparing it to my job as a 911 Dispatcher. Apparently, they are pretty much the same job. He also kept telling me how much smarter and more attractive I was than his ex-girlfriend, who he repeatedly referred to as ‘the evil ex.’
He wants to go to a movie afterward, but I honestly could not imagine sitting through an entire movie right next to this guy (and not just because he would put down his stinky vaporizer). I don’t want to hurt his feelings, so I tell him that I think I may have some mild food poisoning and I needed to get him home so I could make a mad dash home. I realized that if I’d rather claim to have diarrhea then go to a movie with this guy, it’s probably not going to lead to a second date.
Within a minute of leaving his house, he starts texting me about how great our date was and grilling me to get a time for our next date. I finally tell him that I think he is an awesome guy, but our personalities don’t really mesh. He loses it and starts telling me that he’d never get with a fat, ugly girl like me and I should be grateful that he lowered himself enough to go out with me in the first place. Oh, and he hopes I die. I no longer felt bad about not wanting to go on a second date. I haven’t been on a date since then…I’ve decided spinsterhood is more my jam.
I think that people that say this type of thing feel that if they can lower the other persons self worth maybe they will change their mind and come crawling back. Either that or they want the other person to feel as crappy about themselves as they do. Sad either way. Unfortunately, I’ve seen it work a few times and it is baffling.”
“Things Were Going Great…Or So I Thought”
“I got asked out by a girl I knew and was sort of interested in, but didn’t really know all that well. We went to an open air jazz concert, not really my thing but sure.
Once we got there, she immediately was all over me (hugging, sitting on my lap etc.) Things were going great…or so I thought. It was at that point when things started getting weird: several band members where giving us strange looks from stage, while playing their jazz music. One piano player was mouthing things in our direction, but I couldn’t make out what he wanted. People were rude to me for no reason whatsoever while getting drinks.
Long story short: my date knew just about all people there and wanted to get back publicly at her (very large) boyfriend for cheating on her. Don’t hate on me jazzholes, I’m just an innocent sucka!
Awkward ending: I met them both later that evening at the train station and she pretended not to see me.
A Glitch In The System
“It was my second date with this guy and he said the exact same things that he said on the first date. Word for word. The same stories, the same ‘random thoughts,’ the same questions… It freaked me out so much that at first I played along and answered in the exact same way, as though we were both following some weird script.
Eventually, I tried to break the mold and ask him new things, but he would just bring it back around to the same topics as last time. It was like I was in a computer program and there was a glitch. It still freaks me out to think of it.”
Quit Playing Games With My Heart
“I met this girl online, and the way the conversations went it was always friendly, getting to know you type banter. After a few online conversations, we meet up at a bar by her. The plans for the evening were to have drinks there then go play Donkey Kong Country at her place. Being the oblivious male I am, I genuinely was excited to play some DKC on Super Nintendo.
We meet up at the bar and things go fine. I wasn’t really attracted to her at all, but she was nice and we had an alright time at the bar. So we get back to her place and start watching TV. I look around and don’t see a Super Nintendo. Thought maybe it was in her bedroom. I don’t mention it because I don’t want to be rude. She makes some drinks. We’re watching TV, when all of a sudden she looks at me with murder in her eyes, ‘Are we going to stop playing games?!’
I look at her, smiling, trying to play it off, ‘Do you mean Donkey Kong Country?’ She really didn’t appreciate that. She scoffs and then proceeds to chide me about how guys are always wanting to play games and just want to hook up. I told her the only game I was wanting to play was DKC. This is when it got weird. She gets up off the couch, calmly, walks to the kitchen and pulls a butcher knife out of somewhere. She just stands in the kitchen, still with the look of murder in her eyes, and stares me down. She doesn’t move at all, just staring with the butcher knife at her side. I look back for what feels like a few minutes, and then I jump up and dash for the front door.
I didn’t even bother closing the door, behind me I hear the door slam hard, and she’s shouting at the top of her lungs, ‘FREAKING SCUMBAG, PLAYING GAMES. FORGET YOU.’
So a night of what I was hoping to be relaxing, friendly conversation, and Donkey Kong Country, turned into my ‘maybe I could have been murdered’ dating story.
I’m only assuming, so don’t take it for gospel. This was before ‘Netflix and Chill,’ so I think this was her way of getting me back there for something other than ‘DKC,’ but she didn’t want to be super upfront and/or awkward about it. Of course, at the time, I didn’t read it that way. And based on how she was acting, I think she assumed this is what happened with all guys on dates. Or she had super low self esteem. Again, I’m just assuming from my observations.”
“The nurse was a man I met online through a dating website, can’t remember which one. We corresponded through the site and then via phone for a little over a week when I decided to meet him face to face.
We decided to meet at a local Dave and Busters for dinner and games. My sister lives nearby, so I had her as a backup via phone in case things went south and I needed an exit strategy. The best part of the date was the upfront parking space I got which came in handy later. Things went south from there.
I got there a little early, so I waited at the hostess area and browsed the internet on my phone. Before I knew it, I heard my name called and turned to see if it was him. I looked up briefly, didn’t think it was him as the person looked nothing like the pics of the guy I was talking to, then looked back down at my phone. He approaches me and says my name again, which I ignore because I assume this stranger is looking for someone else with my name. Nope. He gets closer and says, ‘Hey, so and so, it’s me, Nurse!’ To which I responded (without thinking), ‘No way,’ while making a face of disbelief because the person in front of me looked NOTHING like the pictures he had posted on his profile (shocking I know). Not a great start.
He acts upset that I didn’t recognize him and tells me the photos are a couple months old (more likely a couple decades old) as I politely nod my head planning my exit strategy. We sit down for dinner and start engaging in some small talk. We talk about college, pastimes, and favorite music. General first date stuff.
As we browse the menu, he starts asking me really personal questions, like have I ever made out or hooked up with another girl and stuff like that. At this point I ask him, jokingly, ‘We haven’t even ordered drinks yet, and you’re asking about my bedroom history?’ All while laughing uncomfortably.
He smiles and responds, ‘You look like a girl who parties. I know you can get some goooooood stuff. Call your peeps and get us some E and some coke. Let’s RAGE.’ This happened literally 10 minutes into the date. We barely have met our waitress at this point.
I immediately text my sister: ‘EMERGENCY! Call now!’ She calls, I answer, and make up an excuse to leave. He calls me out on it.
Nurse: ‘Was that a fake emergency call?’
Me: ‘Yeah, dude can you blame me? You just asked me to get you illegal stuff 10 minutes after meeting me. And you’re a nurse. This is super uncomfortable. I’m gonna go.’
Nurse: ‘Whatever. At least let me walk you out.’
Me: ‘Nope, I’m good. Bye.’
I start walking out of the restaurant and towards the parking lot. As I reach my car, get in and lock the doors, I see him run out of the restaurant frantically. I assume he’s looking for me, so I duck down as far as I can. I hear some one running by, so I pop up and look and see the nurse running through the parking lot and security from the restaurant chasing after him.
Needless to say, I didn’t stick around to find out what happened, but got the heck out of there. I blocked the heck out of that guy on the dating site and my phone.”
His Past Came Back To Haunt Him
“I was on a train coming home from work and saw this GORGEOUS girl. Couldn’t keep my eye off her. Then I realized I used to go to church with her like 15 years before! We weren’t friends. It was early puberty for me, so I was still in the picking on girls and being mean to them phase. But oh well, that’s in the past! I went up, asked her how she’s been what’s she’s been up to. Ah reconnecting! I asked her where she worked and she told me. Turned out we were about a block apart in the city, so I asked her if she wanted to grab lunch one day.
The next day, I text her, we grab lunch, and it’s going splendid, but something is off…she is asking very general ‘first date’ questions. Now, while I’m more then happy to answer, it was bothering me…then it hit me. She didn’t remember me.
I must have been so friendly, confident, or something when I approached her on the train that she agreed to the date. And now here I am, thinking I’m reconnecting with someone, and she didn’t remember me!
Well, the date went great anyway, she had off the next day so we decided to meet up the day after. Fast forward to the next night and I get a text from her:
‘I just remembered who you are. Don’t text me again. Don’t come near me on the train.’
Apparently 12 year old me was a real scumbag.”