Ah, dating. We get all dressed up, do our hair, maybe put on a little makeup, and head out into the world hoping we’ll meet our soul mate sitting across from us at a table. If we’re lucky, maybe that actually happens—but these Redditors were very unlucky. In fact, they had some of the worst dates around, and they knew it from almost the moment they walked in the door.
1. Coming On Strong
He told me to meet him at a bar, which turned out to be a hole-in-in-the-wall in a strip mall, literally just a bar, no food, just booze. We were supposed to be having dinner. I had put in some effort with a cute outfit, nice makeup, etc. When he showed up, my stomach dropped. He had ratty old jeans and a paint-splattered hoodie. That was the moment that made me think "ohhhh this is gonna be bad."
Still, he'd already caught me, so we sat down and the bartender immediately put a pint-glass of tonic in front of him before even asking what I wanted. Clearly he was a regular. We tried to make small talk but he was just so weird. He was cutting me off mid-sentence with random nonsense, buddy-punching me on the arm, and kept hurrying me to finish my drink so I could keep up with him.
I finished my one light drink, paid for it (which offended him deeply), and got up to leave. Then it took another turn. He chugged his last drink, threw a $100 bill on the bar, and followed me into the parking lot. I tried to get away politely and he interrupted with "Come back to my place, I go like a freight train." I stumbled over my "Ah, no thank you" and before I'd finished the sentence he got into his car, started the engine, and screeched out of the parking lot, almost getting it onto two wheels on the turn.
There were some interesting characters back in the early days of online dating. 2004 was like the wild west.
2. Too Close For Comfort
I dated this girl who was a friend of a friend. She used to come into the pub I worked at for $10 steak night with her mom and a guy who we weren't sure was her boyfriend or brother...turned out it was her brother, but they were weirdly close. Anyway, we went on a date, and she seemed quite uncomfortable the whole time. Didn't make much conversation, just obviously wasn't into it.
So I dropped her home, and she asked me if I wanted to come in. Against my better judgement I did. They had two couches in the living room. I sat on one awkwardly while she laid on the other couch and spooned with her brother. At this point I realized I should not have shown up...Every time she left the pub from then on, her and her brother left holding hands.
3. Doing An Ex A Solid
I matched with a girl on Plenty of Fish. We were talking for a while and she worked out she knew someone I had worked with in the past. I asked the previous co-worker what she was like and he said she's ok and not “mental or anything.” Little did I now, this was an evil plan. He actually really didn't like me because I was better at the job than he was and he was straight up lying his butt off.
So I arrange a coffee date between our houses. She only lived like 5-10 minutes away and the nearest shopping centre cafe was 10 minutes away. I arrive and wait a few minutes and in walks this girl 20-30 lbs heavier than her display picture with a baby in a pram. She recognized me and sat down like this was normal. Now see, she'd told me she had a daughter who was two.
I told her I had a two-year-old son as well. Turns out, her daughter was two months not two years and she never corrected the fact. Also this is the first time we had met and she asked me five minutes into the date if I could buy her baby formula. One look at her and I could tell she actually needed the formula and was in a desperate situation, so I bought it for her because I'm a sucker and didn't want her baby to starve.
I then politely told her it was never going to work because she straight-up lied. She said yeah fair enough and left. But that wasn’t the end. About two months later, I was talking to another girl on Plenty of Fish who happened to be friends with her. She seemed normal and not like the complete psychopath I'm sure she was. The crazy one from the first part of the story rang me (she stalked me through my friends) and told me how the second one was mental.
I said I didn't believe her and she hung up on me. Ten minutes later my messenger starts going off, it's girl #1 sending film clips and news articles of girl #2 having a complete psychotic break and torching her ex boyfriends car...on camera in a shopping centre. So it all worked out well and I dodged the bigger bullet because girl #1 thought I was too nice a guy to deserve girl #2.
4. A Blank Slate
When I went on this date with this dude, and he had 0 interests. When I tell you 0, I mean it. He didn’t watch movies, series, did not listen to music, did not watch TV, didn’t have any hobbies, did not have any siblings, any friends, any work, just university studies. He didn’t like to cook or clean or even go on walks. It was the most awkward date I have ever been on with someone.
He was studying Economics, he lived alone, and was an unemployed student. We met on Tinder, and both his pictures and our conversation there seemed normal. I thought he was just shy. But no, he was the most boring person I have ever met in my life.
5. You Again
I went on a date a few months after my college girlfriend and I had broken up. I had matched with this girl off of Tinder and we messaged a bit. But there was one really weird red flag. She was relentless about wanting to know more about my ex and how I felt after the break up. I looked past this and met her for dinner a couple nights later. This was an enormous mistake.
I walked in the restaurant and my ex is sitting at the table under that girl’s name. I turned around to walk out and got a Tinder notification from the girl I had agreed to meet saying, “You’ll never be able to get away from me.” Should have stayed home that night, and steer clear of blind dates.
6. Seeing The Light
I went on a date with a guy on Tinder. He was a co-worker of one of my friends, so I figured he'd be alright. First date was decent enough so we went on a second. This date was also going well until I mentioned his pentagram necklace, asking if he just liked the design or if he was Pagan. He either did not wear this necklace to the first date or it had been under his shirt.
He replied Pagan, and I said how I found the Pagan religion to be very interesting and was hoping to hear more about it. Oh boy, I wish I didn't. He had been fairly shy up until that point. He did a complete 180 and started going on, very loudly in this fairly nice restaurant, about how his mother could physically heal people just with touch and about how his friend was in the army and got shot in the leg but didn't feel any pain from it because my date had linked minds with him from across the world and took all the pain for him instead.
I managed to get through the date and when I got home, I messaged to say it wasn't working out, that I didn't feel any spark after two dates, and wished him well. He immediately blocked me. I then messaged my friend, who was his co-worker, asking if the Pagan talk was normal for him. Friend calls me to cry from laughter over the phone about how he and all the other co-workers knew he was crazy but also knew he was harmless so wanted to see how I'd react to him.
Bit cruel on my friend's part to not warn me, especially since he knew I was going on these dates, but I definitely wasn't going on a third regardless.
7. Three’s A Crowd
I met a girl at a bar and things clicked well. Went on a date a few nights later and she shows up with her “sister.” I didn’t think anything of it at the time. Figured she was being safe possibly since we just met. But this happened two more times. I finally said can we go out without your sister and she seemed insulted at the idea. I found out months later she had no sister, it was just her friend and they did everything together. It was truly strange.
8. The Only Living Girl In San Francisco
We had gone to the Burning Man holiday party. I'm a volunteer so I get an invite and two drink tickets, but she hated it and made me take her to a nice restaurant around the corner. It was a nice place in the Dogpatch neighborhood. And I guess the whole time the staff slowly came to hate her and worry about me. She didn't like anything and didn't look at the staff much.
When I drove her home, she accused me of being a recruiter for a cult. I still asked her out again, though, God knows why. I showed up and she had forgotten so we went to a deli next door where she got in an argument with some street guy she seemed to really vibe with. I finally lost interest when we were walking very fast in a random direction and she went on about how she was the only person in San Francisco opposed to assault.
I gently disagreed so she turned and walked away. Should I call her?
9. Secret Messages
She texted me an apology for the date while we were still on the date. Long story short: she arrived late, then friends of hers "just happened to be walking by" and they joined us. Clearly, their intention was to use me for free drinks, which they immediately began guzzling down as quickly as the server could bring them. I realized what they were doing, so I made sure to pay for my drinks in cash, which meant I didn't have a tab going.
I tried to give my date the benefit of the doubt in hopes that her friends would leave and we'd actually have a date, but she seemed more interested in getting their approval. At one point, she was staring down at her phone, and then mine started vibrating. Normally, I'd never check my phone while on a date, but this date was a disaster, and she was obviously staring at her phone, so...what the heck.
I looked down at my phone and saw a one-word text…from her. It just said “Sorry.” I looked at her, then I looked at my phone again, and I just shrugged. Whatever. There was a gasp when I got up to leave. One of her friends protested because I didn't pick up the bill for the whole table. I said, "I already paid for mine." Then I walked right out of the door.
Sign up to our newsletter.
History’s most fascinating stories and darkest secrets, delivered to your inbox daily. Making distraction rewarding since 2017.
10. He Almost Fooled Her
I went on a couple of dates with a guy who genuinely seemed really nice. For our third or fourth date, he invited me to go tailgating with his family, who I clearly didn’t even know. I said yes because I’ve never been tailgating before. He quickly made me regret saying yes. I went over to his place and was invited into his room. There was no bed frame, no sheets, crumbs from food everywhere, clothes were partly folded on the floor, it was dimly lit, and the carpet was crusty enough that it had gotten stiff/hard.
Absolutely disgusting. His family ended up being friendly, but when it was time for me to go that night, he quite literally pouted like a child and initially refused to take me home. I should’ve drove myself, but didn’t. Hindsight is 20/20. On our way back to my house, he started talking about how he was going to spend $10k on an engagement ring for me and how he wanted to marry me “so badly.”
He also brought up that his last “girlfriend’s” father threatened to call the authorities on him if he didn’t leave her alone. The following day, I texted him and said that things weren’t going to work out. I blocked him after he messaged me really weird things and said he “just wanted to get a reaction out of [me].” I just hate how the red flags didn’t pop up on the first couple dates.
11. Dr. Jekyll And Mr. Hyde
I met this guy on Tinder. He seemed really cool. We started texting for a month or so and later planned to meet at this tavern. It was hard trying to find him because the place was packed. When I do see him, I guess he’s tipsy. But he didn’t seem like completely out of it, he was functional. I tried to ask him questions and get to know him in this sort of loud and busy space.
The whole time, even though he’s inches away from my face, he can’t hear what I’m asking or saying. Mind you, he invited me to this place, I’d never gone here before. This was supposed to be our first date. He proceeds to buy me a pint and kept slapping me on my backside, quite forcefully to be honest. This is my first time meeting him. We get the drink and he asks me “Do you want a drink?” Alarm bells start going off.
I tell him he just bought me one. He asks this question annoyingly over and over again as if he forgot he asked already. This goes on for at least an hour…All the while I’m trying to kick it with him. Play some outdoor bar games and such. And he’s asking, “What are you doing here?” And I’m like “I’m on a date with you?” He asks me this question over an over as well…
I don’t get how anyone is that incoherent. He wasn’t that far gone, he couldn’t have been. Even if he was, when we texted he seemed fairly intelligible and kind. But the whole night he probably only asked me two or three questions, the same ones, over and over, and kept slapping me on my backside. There was a point we were going to congregate with his friends and I sort of lost him in the crowd and LEFT. Very rude and weird.
He had the nerve to call me and asked where I went. I told him I went home. He said he wanted to get to know me, and I was like yeah, maybe another time. Like dude you had the whole night to try. He had no intent to make a real effort. I blocked the heck out of him.
12. Honesty Isn’t Always The Best Policy
We had a great time at dinner, and went for a walk through a park afterwards. We're walking along and talking. Then she makes a shocking confession. She mentions to me that she is still "technically" engaged to a guy, but she was only marrying him because he had gotten her pregnant. But she had had a miscarriage a few days ago (had not told him yet), and now that there was no baby and she had met me she was going to tell him and break up with him.
There was no second date.
13. Don’t Follow Your Dreams
When he went on a long and obnoxious rant about how my job at the time (assistant welder) was "stupid and a waste of time" and that I should become a dental hygienist, a job I have no interest in, because "at least it has a future." The whole date itself was AWFUL. But it was at that point I realized, we were not a "match," to say the least.
14. Never Gonna Get This
I didn't show up for this date, and I was always super proud that I trusted my intuition. I had a date scheduled with a guy at a nice place downtown that I had agreed to. Right before the date he leaves me a message that we're going to a different place. I look it up, and it's a dive bar out in the middle of nowhere. Like in a field. Alarm bells started going off.
I actually really liked the guy and went back and forth with myself before I call the guy back and get his voicemail. So I leave a message apologizing profusely, but I need to reschedule the date. I also add that I'd like to pick the place this time. Alarm bells are still going off and I end up letting his return call go to voicemail. I'm glad didn’t pick up. His message sent chills down my spine.
I had to listen to it twice to believe it. This grown man proceeds to scream at me, calling me every name in the book. Calling me a witch, etc. Telling me how I missed out on the best date with best guy of my life. That was the most happy I'd been I went with my gut and skipped out on a first date.
15. A Lie Of Omission
Weirdest date I ever had? Probably the time she was hiding the fact she had a baby. She didn’t say anything about that when we were texting each other days prior. But that wasn’t the deal breaker. The deal breaker was the fact she had a baby and was alcoholic that couldn’t keep herself under control and also mentioned that her ex (currently behind bars at the time) didn’t really “break up” so I figured she was trying to keep me as around as a rebound.
16. Now Let’s Talk About Me
I’m not sure what was the exact moment I realized I shouldn’t have showed up to this date, but I think it was at some point during the first 10 minutes. She showed up 30 minutes late and her “apology” was “Sorry I’m late but I’m always late.” Then she spent the first 15 minutes talking about her ex who she just broke up with a mere three days ago. And it STILL got worse.
During the entire date, she asked zero questions about me and only talked about herself and her problems. Gossiped about her friends (who I didn’t even know at all). Spent 20 minutes showing me photos and videos of her cat. I usually like cats but I was really annoyed at that point. Complained about the ice in her soda. And spent the last 10 minutes of the date talking about how much she needs to pee but refused to use the public restroom.
I was so glad when that date was over.
17. Am I Bothering You?
I went to a movie with my date, and everything seemed okay. We decided to grab dinner after the movie, and she just straight got sucked into her phone. Like, more than anyone I've ever seen. After more than a couple minutes of just sitting awkwardly and dumb small talk, I asked her if she had something going on or if she needed to go. "No I'm fine, just checking all my socials and keeping up with a few convos. You know how it is."
No, I don't. We had already ordered, so I just sat there quietly for the next 20 minutes until I got fed up with it. I said "excuse me for a moment," got up and told our waiter to put mine in a to-go box, and sat in the waiting room. She never looked up the entire time. Paid the waiter for my meal, and left.
18. The Wrong Kind Of Double Date
It was midway through the movie and she said she had to go to the bathroom. She then came back with her boyfriend, who I wasn’t aware existed. So he sat in between us and swapped spit with her while I sat. I just walked out and went home afterward. Didn’t say goodbye or anything.
19. A Mountain Of Lies
I met a woman and she went on a diatribe about how into mountain biking she was. I asked her if she'd like to go mountain biking for a date and several days later we went. I picked her up and her roommate gave me "that look," like "good luck." There were a lot of verbal (sassy/complaining) and facial clues that said "this is not the date you're looking for."
We got on the trail and within about five minutes I realized she was not in fact "into" mountain biking. She pouted the entire time. Afterward I dropped her off, and she said something like "I had a nice time" and all I could do was think "are you kidding me?" There was no second date.
20. Child’s Play
He took a weird interest in me working in childcare. Kept bringing up kids and toddlers. Eventually he made it clear he wanted a lot of kids and wanted me at home taking care of them. Which…whatever, I like the idea of being a housewife. Just the way he came across was bad and misogynistic. He told me at one point he’s not touching the kids till they’re out of diapers. That’s my job.
At that point, I knew I had made a mistake. Problem was, he was also my ride since a friend dropped me off. Had to go home with him.
21. Getaway Car
When she asked if we could stop at her mom's house first so she could "grab something," then after 10 minutes of waiting in the car she came running out of the door carrying a baby and a woman was chasing her, screaming. She jumped in the car and started yelling "drive drive drive!" I knew exactly what I had to do. I turned the car off and got out.
It was her kid, but she had lost custody to her mother because of addiction issues. We had met on a dating site and she thought I would go along with her plan to take her child back. She spent that night in a cell.
22. He Should Have Watered Himself Down
When he walked into the café we were meeting at with a 4L jug of water, plopped it on the counter, and told the barista to use his special filtered water for the tea he was ordering. Turned out he sells these water purification machines that optimize the PH...which he insisted was not a pyramid scheme (it definitely was). After enduring his awful sales pitch, he also told me he used to be a drug dealer and that he turned to selling water because "he's addicted to selling." But that wasn’t the worst part.
He also told me how he had “extremely old fashioned values” (his words) and that he is a very controlling person and can't help it. He said he hates when people waste his time and is looking for a wife. Every time I tried talking about anything, he would cut me off and start talking about himself. He offered me a ride home at the end. I politely declined and ran the second I was no longer in line of sight.
23. Dads Always Know Best
He got into a political rant about 15 minutes into sitting down at dinner. And then opened his mouth and goes “Minorities wouldn’t have it so bad if they just worked harder. Opportunities don’t just fall into white people’s laps.” I excused myself to the bathroom, went to the hostess, paid my half of the meal that I didn’t even get to eat, and walked out.
I then went home and told my dad, who then made me an awesome grilled cheese and a hug. He also said I should have just left him with the bill and I have to agree but I just felt too nice to do that.
24. Don’t Just Be You
One of my first attempts at online dating many years ago was a total disaster. The girl wasn’t very bright, but she was really nice and absolutely beautiful judging by the pictures she’d sent me. As a little background, she told me she was 5’2 and worked out, and had an average to slim body. I didn’t think anything of her telling me her height because she asked me mine, and that’s not always easily deduced from photos.
But her telling me that she worked out and had an average/slim body was odd because that was clear from her photos. After a couple weeks, we set a time and place to meet. I arrived at a park near a gazebo she said she would be at. I looked through my windshield, but all I saw was this really tall, obese woman wearing pajamas standing inside.
She was easily 6’4” or 6’5”, certainly taller than I was. I thought maybe she was late, because clearly there was no 5’2” petite female in sight, so I call the girl. I’ll never forget what I saw next. I see the PJ woman’s flip phone light up and play a song I didn’t recognize, and she answered. It was her. She said “I see you,” immediately hung up, and started walking towards my car.
That was the moment I knew I’d wasted an hour of my time driving out to meet a stranger. I hit the lock before she could open door and rolled down the window with a “do I know you?” She said something along the lines of “Yeaaahhhh, I’m a bit taller than I said.” I apologized, said I had to go, and I pulled away. Whatever my type of girl, starting out any relationship on an easily verified lie is a gigantic red flag.
She texted me a minute or so later and told me it was screwed up of me to make her get ready to go out just to leave her hanging. Her version of “getting ready” was putting on old unwashed pajamas. I ended up hanging out with some friends I hadn’t seen in years that happened to live 20 minutes away, so it wasn’t a total loss. Bullet dodged, nonetheless.
25. When Dating Is Free Therapy
She was a kleptomaniac. I thought she was exaggerating or maybe just went through a tough time. Then she showed me the pile of paperwork. She was on first name terms with the judge because she had been to court so many times. Then she asked me to touch her back. Said she felt super sweaty from the MCAT she'd taken and then showed me how she disposed of her used needles because she was an addict.
Should have noped out sooner, but she was sweet. But yeah, she needed a therapist, not a boyfriend.
26. Putting Out The Wrong Signals
I went out for coffee with a girl. She seemed really nice and cute over texting...Woof. I was wrong. Got there, and she looked vaguely like her photos, but had multiple decayed black teeth, smelled horrendous, and had breath that was so bad that the people in the next state could be hurt by it. She was also really, really...odd. She wasn't mean or rude, but just sort of overall lacked personality, in general.
What really did it was the overall hygiene, though. It was repulsive. At the end of the date we walked to the cars, gave her a hug goodbye, and then she questioned when I was going to kiss her. I tried to be nice and say I don't kiss on the first date, good guy, etc. but she wasn't having it apparently. She stuck her tongue straight into my mouth and said she can't wait for next time when we can have more fun, wink wink.
I sat in my car questioning my life while chewing multiple pieces of gum. It took several rounds of mouthwash to get her taste out of my mouth.
27. Making Small Talk
This would have been in late 2011- early 2012, when Plenty of Fish was still a popular online dating option. This would have been my second (and last) date from online dating. I chatted with this one woman for a few days. She had similar interests and her picture made her seem pretty cute, so I was interested. The day before our date she admitted the picture of her was actually her friend.
She sent me a picture of her from the bridge of her nose up. She had pretty eyes, and I understood the shyness of putting your actual picture out there, so I still went on the date. Her face was…pear shaped to put it bluntly. She was kind of slim, but also chubby in places you don't really think of when you hear "chubby." Anyways, we sat and had coffee, and she only wanted to rant about her mom and little brother, and how unfair it is she had to watch him the previous night.
Considering our online conversations were about video games, music, and TV shows we liked, this was a complete 180 for her. I tried steering the conversation to anything else, but she persisted. We both would have been 21 at the time. I left and told her we weren't a good match, then I deleted my profile later that night. No more for me.
28. Food For Thought
I was supposed to pick him up at his Airbnb so we could go out for dinner and drinks. Turns out the place was actually his parents’ house. I thought it was weird that he lied about where he was staying but figured he was just embarrassed so I didn’t make a big deal about it. When I suggested a place I wanted to go for dinner, his response made my hair stand up on end.
He told me his parents made dinner so he wanted to stay there to eat and go out for drinks after. I felt super awkward about having dinner with his family on our first date, but it got worse. He made me a plate of food, had me sit at a table in the garage, and told me he’d be right back. Then he went inside and had dinner with his whole family while I sat alone in the garage.
I wish I could say I noped out of there, but unfortunately I stuck it out for the worst date night of my life.
29. Crazy Cat Lady
I was the bad date: Got super hammered before I got there, talked A LOT about my cat. Invited him in, basically talked him into it. I really wasn't planning on bringing him, so I get undressed and I'm wearing cat underwear, which I know added to my crazy cat lady allure because he commented on them. After finishing some lousy love making, he goes to get dressed and finds my cat sitting next to his cat pee-soaked clothes. Poor guy.
30. Getting Back In The Game
This happened to a friend of mine. He had recently broken up with a long-term girl and was looking to “get back out there,” but was too cheap to pay for a dating service so stuck to free ones. He sets up a date with a girl to come over to his place and do some hot tubbing. She shows up and wants some specific kind of drink, I'll say goldschlager, which he didn't have.
So she insists they make a store run. She seemed sketchy, so my buddy is about 50% sure he's going to get robbed, so he tells her to drive and deliberately “forgets” his wallet and phone at home. He had no idea what he was in for. When he gets in her car, there's no passenger seat. She said she has a huge dog so she took the seat out, and he has to sit in the back seat.
The date was late, so the closest store is closed. Rather than go back to his place, she says she knows a store that's open late. He says they're all state stores, they all close the same time...she won't listen and they hit the highway. After a while, he starts to wonder where they're going, and says "Where is this store?" That’s when she screams. She had forgotten he was in the car because he was in the back seat.
My buddy now accepts that she has been drinking for some time. She won't stop or pull over to let him drive, just keeps driving. Turns out the late store is about 30 minutes from his house, and she forgets he was in the car twice more on the trip. They get to the store and it's closed, as expected. This is when she snapped. She gets out anyway and is doing the jerking the locked door thing and yelling "HELLO!" over and over.
My buddy is out of the car watching this as she starts yelling at some sketchy-looking dudes drinking 40s in the parking lot. She starts with "why is this store closed" and quickly escalates to profanity. My buddy takes this as his opportunity and just walks away, doesn't even look back. Now he finds himself 30-minute drive from home, with no wallet or cell phone because he was so smart.
He eventually gets a convenience store clerk to take pity on him and he called his brother to come pick him up. He said he was worried about the girl showing up at his house, but he never heard from her again.
31. Off The Deep End
When she was speeding in the rain, driving in the opposite direction of the restaurant, telling me how her parents had her admitted to a psych ward, but she didn’t take any meds because there was nothing wrong with her! I convinced her to stop at a Chinese restaurant instead of a coffee shop because an immediate dinner would have been a shorter evening than a coffee shop on the other side of town.
Afterwards, I told her to take me back to my car because my mother was in town. In the parking lot, she insists that I should not see my mother because I have seen her my whole life, but she and I were just getting to know one another, so I should prioritize my time with her. When I ignored her future calls, she continued to stalk me for months, followed me around town, spied on me running errands, showed up at my house unannounced, knocked on my bedroom window at all hours of the night, left food at my door, left love notes on my windshield, etc.
I was very close to filing a restraining order, but after I physically removed her from my place and my roommate told her I would get a restraining order, she only stalked me on campus.
32. Shooting His Shot
So I met a girl on Tinder (I am also a girl). Let’s call her Cecelia. We plan to meet up for coffee. You know, nice slow date, let’s defy the U-Haul stereotype. I get there, and a guy comes up to me. “Hey, are you Kate?” “Yep.” “I’m Brent. Cecelia’s my cousin.” “Oh, could she not make it?” “I was using her pictures. You were talking to me on Tinder.” “Why?” His answer floored me.
“Well, straight girls are so judgmental. So I decided it might be easier to just get a lesbian to turn. You liked me when you thought I was a girl, let’s give it a shot.” Did not give it a shot. Ended up tracking down the real Cecelia through social media and telling her what Brent was doing. Unfortunately, she was not actually a lesbian and I remain chronically single.
My last two dates would not talk about anything but astrology and cryptocurrency, respectively.
33. The One That Got Away
A guy asked me out to lunch. I dressed cute that day. On my lunch break, I met him at his place of employment. We went to the filthy break room/store room where he instructed me to sit on an upside down bucket. He began to prepare a packet of cheesy pasta in the microwave. He served me this tepid glop in a Styrofoam bowl. Then he spent the entire time talking about his ex-girlfriend, who looked like a Renaissance goddess and wrote amazing poetry.
Several years later, I became friends with this woman and told her about this “lunch date” and she was mortified.
34. She Didn’t See This One Coming
I was using a dating app and this woman had messaged me first and we had a few great conversations. She was listed at 35. She suggested that we meet up, have a meal and then see where things go. I show up to her place to pick her up and as I am waiting, a 65-year-old woman approaches my car. She introduces herself and I ask her how old she is and she says 35.
I ask to see her ID, she declines and she insists we go get a meal. I politely tell her that the start of any friendship or relationship needs honesty and I would kindly like to know her age as it is obvious she is not 35. Keeps saying she's 35. As we are driving (I am going in circles under the pretext of going to a restaurant) I ask about her life.
She gets interrupted by a phone call she must take as it is from work. She asks for me to pull over to let her talk, I do. She doesn't exit the vehicle. I then hear a conversation that makes it all make sense. She works as phone psychic, and I sit there listening to her faking it to a lady who sounds like she is in need of help, explaining they pay $9.99 the first minute and it goes up from there.
After her call ends she says, "Easy $12." So I resume driving, now headed back to her place which she doesn't realize, and I continue asking her about herself. She drops that she has a son who is 31. I brake as I start laughing and say "So you gave birth at four?" She starts mumbling about how she misspoke but I pulled up in front of her building and politely asked her to exit the vehicle as dishonesty is a deal breaker.
35. Game Night Gone Wrong
An alleged friend told me her co-worker and I would be great together and wanted to do a double date at a festival with her and her husband. The date suggested he and I meet up the night before to get to know each other and I suggested a gaming bar I'd wanted to try. Date time arrives and he's not there. He finally shows up and tells me he had to stop home to let the dogs out so they don't poop all over the floor.
He then proceeds to show me a picture of a floor covered in dog poop and says, “Guess it didn't work.” He is still wearing his work clothes. It has been three hours since work ended and he went home to deal with the dogs but didn't change. He proceeds to eat the rest of the charcuterie plate I ordered by himself and then orders wings for himself.
We decide to check out a game since I have now paid for more game time. He wants a mall madness game that is not designed for two people. We settle on a playable game. It's not great. As we are wrapping up, he tells me the last date he took here hooked up with him in the parking lot. He then stares at me expectantly. I tell him that's not going to happen.
I tell my friend I'm skipping the festival. He's shocked and thought we had a spark.
36. All Over The Shop
He was picking me up and texted me "here" a little early, so he had plenty of time to do this before I got down to his car. But no, he waited until I opened the door and there were about a dozen right-wing magazines on the passenger's seat. He said, "Hope you're not some crazy liberal! Don’t mind these mags" and then brushed them onto the floor.
It was super awkward and cringy. It was my first date since a rough breakup and the rest of it was just as bad if not worse. I ended up crying in the bathroom halfway through. Also, he picked me up in a Prius—which like great car, save gas and what not, but also like the antithesis of what you would expect from someone whose first comment to me was “hope you’re not some crazy liberal.”
For the rest of the date he just kind of ragged on me, like he asked me my hobbies and I said scuba diving, and he went on and on about how that’s bad for you and he free dives soooo far down and can hold his breath soooo long that he doesn't need air on his back; he's in such good shape! I was like okay. He asked me if I cook and I told him I'm a bad cook but I don’t care because I'm not a picky eater at all.
He went off about how his mom was such a good cook and "southern values" and how it’s so unfortunate I can't cook. He didn’t outright say “as a woman” but still comparing me to his mom a bunch and using phrase "southern values" alluded to that. Then I think he could tell we had NOTHING in common so he asked if I would mind if his friends would join us.
I was like sure, honestly excited because I figured they had to be better than him and assumed they would be our age, in their 20s. They were 60+ year old fishermen. Honestly, though, that was the highlight of the date. They were kind of cool, and it made sense to me he did not have friends our age.
37. A Family Affair
I showed up and her best friend was there. I hadn’t been warned she was coming with us. Then her brother showed up. Then her dad showed up. Then her mom and her three of her cousins aged 3-5 showed up. That was the point I excused myself to go to the bathroom. THANKFULLY this is one of those places where the employees will sneak you out if you’re having a bad date and need an out, and apparently I’m the first guy they snuck out at that point.
38. Fancy Meeting You Here
Before our first-ever date, which he told me he wanted to plan, I’d told him I had been vegetarian for a few years now and as long as where we went had vegetarian options, I didn’t mind where it was. He brought me to a steakhouse. Said he’d forgotten I’d said that. I ended up just having fries the whole night. Points to him, he did seem like he had actually forgotten and the conversation was good so I agreed to a second date.
Now, I had also told him I was caffeine intolerant—couldn’t have any coffee, Coke, most teas etc. And where did we go? To the university coffee stand. I left to go to my archaeology class and my desk buddy tells me we are getting a new tutor because our first one got sick and couldn’t see the rest of the semester through. Guess who our new tutor was? Mr. Steakhouse and Coffee Stand Guy.
I maintain to this day that it was worth it all just for the look on his face when he walked into class. I wish I was making this up.
39. Moving Fast
Drove 50 minutes to her small town to watch a movie. Turns out she meant at her place, and it was a sequel to a trilogy I had never started. She was pretty awkward, which was fine but then she started REALLY over sharing saying she was a crack baby and telling me all her trauma. That was the point I knew it was a mistake, considering she had fibbed her way into the date.
By the end of the night she was telling me she loved me. I left shortly after that and I let her down over text once I was home. Cherry on top: she got pregnant three months later from her boyfriend of five months.
40. Kind To Be Cruel
I waited on the park bench next to a girl for about 30 minutes after the agreed-upon time I was supposed to meet my date. Turns out I was sitting next to my date the entire time, I just didn’t recognize her because she was at least 200 lbs bigger than any of her pictures with no similarities. Turns out her much more attractive friend was trying to help her out by making a Tinder profile, using her own pictures, doing the matching and flirting, and then letting her less attractive friend actually do the meetings. She should not have tried to help.
41. Joking Around
I went to this guy’s house to play Magic after meeting him at my local store a couple times. I excused myself to pee. It took a very dark turn. As I was peeing, he stood outside of the bathroom door and did an awful impression of the Joker laugh while saying he’s been waiting for someone like me and other extremely creepy phrases about how I am “perfect for him.”
The post peeing bathroom exit was so absolutely awkward. Riddled with me saying several different versions of “Oh wow, that was a great Joker impression haha” and him continuing to speak like the Joker. It was the longest, most tense, fearful walk down the stairs. I left shortly after that. It still haunts me.
42. Only One Woman For Me
He said how he missed his mom and started crying because the music reminded him of her. She's alive and all. Just wasn't there at the restaurant with us.
43. Tell Me How You Really Feel
When she live-tweeted the date and said she didn’t want to be there…at the beginning of the date.
44. Dress The Part
That time when I walked into the restaurant where I was meeting a “Dr.” was the worst date I’ve ever had. I met him online, and he was there wearing a white lab coat….to dinner…our first (and last) date.
45. From A Yes To A No
When he asked me out and I said yes, he then asked if I’d like to go to dinner and what kind of food I liked. I said anything but sushi. He took me to a sushi place. Said he thought he’d be able to change my mind.
46. A Real Winner
I suggested a Tinder date meet me at the Hirshhorn Museum in DC. He showed up, said, "I hate art" and then touched every single piece of it until a guard saw.
47. Disappearing Act
We matched on Bumble and hit it off. She asked if I wanted to talk on Snapchat instead. I said sure. We had a good time and I asked if she wanted to go out for dinner that week. She said yes, so I suggested a place between our towns so neither of us would have to drive the full distance. She said she wanted to be closer to her house, and that she knew a nice, low-key Italian place in her town.
I said okay, and we continued talking until the date. We were sending pictures on Snapchat, so there was no catfishing on either of our ends. We knew we were the people in our profile pictures. So the day comes up and I drive the 55 minutes to her town. We meet up at the restaurant, everything is smiles and laughs. Sit at the table, the waiter asks what we’d like to drink.
I get a water, she says she’ll have the same. I ask her what’s good on the menu, because she said she’s been here before. She names off some things, tells me what she plans on ordering. I take one of her suggestions so we could spend time talking instead of me looking over a menu she’s already familiar with. I asked her how her week went, she told me about how much of a hassle work was.
She worked in cyber-security or something like that, and I asked how she got into that line of work. She started talking about her major and where she studied. She asked me about school and what I studied, I told her and said I was now in grad school full time while working part-time as a security guard at night. One of us made a joke about how we both do security in some way, and we both laughed. I could have had no idea what was coming.
The waiter came over with our drinks and asked if we were ready to order. We both ordered, and he walked away. IMMEDIATELY she says she needs to run to the toilet really quickly. She grabs her bag and coat and leaves the restaurant. No urgency to it. No shame. Nothing in her voice to suggest she was having a bad time. It was all very casual.
Now, I have both a friend and a family member who refuse to use public restrooms, so my mind immediately said “Oh, she wanted to be close to home in case she had to use the toilet. That makes sense.” No big deal. After about 15 minutes, the waiter comes over and delivers our dinners. I say my date had to step out but should be back soon.
I wait about ten more minutes and start eating, because the food was getting cold. I text her something like “Hey, is everything okay?” She doesn’t respond for another ten or so minutes. When she does: “Yeah!” I text her, “Are you coming back? The food’s getting cold lol.” Her response still shocks me. She says “Nope!” One-word responses, with exclamation marks.
At this point, I’m confused. I feel like I didn’t stress this enough: We ordered our food and then she IMMEDIATELY got up and left. It wasn’t that we ordered and I said something that made her uncomfortable. She said she had to use the toilet before our waiter had walked even five steps from the table. So not only am I confused at this point, but I’m kind of angry.
I drove almost an hour out, and now I was going to have to pay for an uneaten meal? So I stewed over a text for a while, trying to come off as, well, not upset. I texted: “Oh…okay? If something suddenly came up we can reschedule? I don’t know why you wouldn’t just say so though?” And she said, “No, nothing came up. I just didn’t feel a spark.”
Now, I’m sure we’ve all been to a restaurant before. It doesn’t take long for a waiter to bring you your drinks and ask if you’re ready to order. Maybe 10 minutes, max? So we talked for 10 minutes, at most, with the bulk of that time being her talking about her work—mostly gossiping about co-workers that I don’t know. Then she deliberately ordered food and left.
You’d think if she wanted to leave she’d not have ordered first? Anyway, I finished my dinner, the waiter came over and asked if I was done with my plate. I said he could take the other one too because my date had walked out. He said, “Before the food showed up? Rough.” I said, “Actually, she left right after you took the order.” He kind of laughed and said, “Darn, sorry man. You want a drink?”
I said I shouldn’t. He said it was on the house. So I said sure, thank you. He got me a drink and came back later with the bill. I said the second meal wasn’t on there, and he said, “You’ve had a tough night, don’t worry about it.” So I tipped him $16, which was what I estimated the cost of her meal to be. Never heard from the girl again. No idea what that was all about.
48. This Is A Girl Who Can Multi-Task
I was 18, a girl sent me a message on MSN saying she got my details from my friend and wanted to go on a date with me. I asked my friend and he said she was hot, so after talking a bit I agreed to a date. I had seen a photo and she was attractive. I turned up at the cafe for the date. It all went wrong instantly. I was approached by some girl I'd never seen with a baby.
She then told me she was the girl, even though she looked nothing like her photo. She explained she thought I'd never go for someone who looked like her (she was right). But that wasn’t all. She then left her baby with me while she went to the toilet quickly. Alarm bells started to ring after 15 minutes. I asked a waitress to check on her.
When the waitress came back, she told me news that made my blood run cold. She said no one was in there. I looked around the cafe and she was gone. I hadn't noticed her leaving. I didn't have any of her contact details and smartphones were not a thing so I didn't have internet access. I phoned my friend and got him to attempt to contact her on MSN.
After telling him what happened he was surprised and had no idea, apparently he also thought her pictures were the real her. Another 20 minutes went by and I was scared so I asked the waitress for help. Thankfully she was able to help and called the authorities. They showed up and I explained what happened. I didn't know anything about this girl so I couldn't really help them.
They said if she contacted me to get her to contact them. I left and walked towards my car, and in so doing I went past another cafe about six shops down. I couldn’t believe what I saw. There she was with a different guy. I went back to the officers and got them to take her baby in while I watched through the window outside and waved when she looked up. Turns out I was the babysitter for her real date.
49. Emily Post’s Long-Lost Brother
While perusing the menu, he asked what I was going to get. I said "Um, I'm thinking about…" and he cut me off to say "They don't have UM here." I chuckled and continued "So I think I'll have the uh chicken." He responded seriously with a raised voice, "They don't have UH CHICKEN here either" and shook his head like I was annoying. I just stared at him for a minute.
50. Bait And Switch
When she responded to a “Hi” on Tinder with something like “hey cutie, want to come to my parents’ house?” We chatted for a bit, and according to her she wasn’t looking for anything serious but she wanted me to pick her up, take her out to dinner, and maybe get it on afterwards. Very transactional, which kind of stung but whatever she was hot.
I looked up the address she gave me. When I read it, I got a small, dark feeling. I was surprised to find a neighborhood I did some work in, and that the house was one I knew was for sale. Specifically, the owner passed and it was being gutted to be resold by his kids. At this point I was 100% convinced this was a scam, but somewhat curious, I decided to drive by and see if anyone was there.
I texted her I was coming, but in a different type of car. It was a really expensive neighborhood on a sea-cliff, and it felt like an adventure. I took my work truck. I drove by and some huge dude comes out of the house, stares at my truck, and goes back in. I could see other people inside. I noped out of there super fast. Pretty convinced it was a phishing scam to mug me, or a prank. Didn’t feel like finding out.