Dating is tough…

There are bad dates and then there are really BAD dates.

And these stories on Reddit are most definitely the latter.

[deleted by user]
by inAskReddit

Enjoy the cringe, my romantic friends.

1. The “park”

Met a guy in OKC when I was in between HS and college. We got chatting and agreed to meet for a date. Since we were both young and broke he suggested a park in his area. Said he’d bring drinks if I bring food. Sure! Packed some snacks and a blanket thinking picnic.

Got to the address he gave me and it was his apartment complex. The “park” -more like a grassy area for dogs- was apart of the complex. I had pretty low self esteem from a recent break up so I just said, what the h**l let’s see where this goes…

He met me at my car and we walked around for like 10s when he mentions he left the beer up in his apt. Once in his apt he immediately tries to shove his tongue down my throat. I made some excuse and luckily was able to leave.

Still think about that sometimes and shiver.

– Main-Yogurtcloset-82

2. Size doesn’t matter

As a relatively recent “mature” widower, new and inexperienced to the dating scene after 31 years of marriage, I had a dinner date with a much younger woman who, as it turned out, was extremely aggressive… unheard of in my prime!

Ending our first date, I was dropping her off and had intended only to give her a thank you peck on the cheek, however our “goodbye” moment morphed into a high school-like make out session during which she started, shockingly, to grope me.

My two-seater car was dark and cramped and I was wearing a suit and winter overcoat but I nevertheless was extremely surprised to feel her hand navigating south of my belt. Suddenly she squeezed hard and, with sheer delight and fire in her dimly lit eyes, delightedly exclaimed that I had “an enormous penis”.

In fact, she was squeezing a single large roll of my lower belly fat!

For the first and last time in my life, I glanced at my pretend wrist watch & told her that I had to leave due to the late hour and an early morning meeting. I couldn’t imagine her reaction and disappointment had our date developed any further as I am, at best, average! I bailed and we never spoke again.

– Dajackash

3. Going hard

I talked to a girl on tinder 8 years ago. She got drunk and told me to come over because her and friends were playing strip poker. I was on overnight duty so sadly I could not partake.

30 minutes later I receive a picture on my phone that i couldn’t even make out. I handed my phone to my roommate and asked if he could figure it out. He says “dude. That’s a butthole.” It surely was. She had taken a picture of her butthole from at measly 0.5 inches away and it was so close up i could barely tell what it was. I thought to myself if this is how she leads the rest has to be great! (Spoiler alert: was wrong.)

She tells me we should finally meet next weekend. At Applebee’s. I meet her there and she looks BEAT. Like she had just run 5 triathlons and been awake for a week straight. Not 3 minutes into meeting and sitting down she says she has to use the restroom.

She doesnt come back for 30min+. The waiter comes up and says he has seen her here multiple times and she has been known to shoot up heroin in the bathroom and pass out. Im very not into this at this point but for her own safety i ask if a waitress could peak in the bathroom and see if she is okay. She was not. She OD’d and died. So that was a thing.

– roughactionhank

4. The end of all jokes

Literally s**t myself on a date once….wasn’t technically a date, but the guy had a farm.

He took me to see the animals, feed, ect. I walked away for a few minutes and over trusted a fart. I just looked at him and asked if he could please take me back to my car…he wanted to know why and I said “because I pooped in my pants”

Guy had a super nice truck and made me sit on my feet all the way back to my vehicle.

We actually ended up dating for 2 ish years….and somehow me sh**ting myself on the first date was the end of all jokes.

– No_Bet4331

5. The proposal

Not necessarily a date but a person I was dating invited me to his parent’s house for the afternoon. He wanted to introduce me to them and show me the house he grew up in. I thought it was super sweet and had no problems going. He was also in the middle of moving and needed to pick up a few things, so it really didn’t seem that unusual.

Yeah, we got there and it was awful. His entire family was there. They traveled from hours away too. This was not just meeting the parents, it was meeting the ENTIRE family. Even worse? At some point, this jacka** told his parents that he had proposed. We had been dating TWO months.

I spent the entire afternoon dumbfounded and just playing along. We were two hours from home and I had no cell service, no way to leave at all. We ended up spending the afternoon brainstorming wedding ideas and planning an Alaskan honeymoon that his parents planned to gift us. His brother even called to say congratulations!

We drove back to his apartment in silence. When we got there, I got in my car and left, didn’t even bother grabbing my stuff. Weirdest experience ever. I have no idea how he broke it to his parents that we weren’t getting married.

– andandandetc

6. The King

Was told we were going to dinner and then shopping. I drove to the town, 1hr each way, cuz he didn’t have a license.

He directed me (didn’t know my way around at all) to… Burger King. Ok. I’ll work with it.

Standing in line, a worker accidentally leans on a packet of ranch. It breaks open and shoots at me, right on the front of my nicest shirt. Profound apologizing commences. I ended up paying for dinner too.

Then we went to… Walmart. Where his mom worked. So he could get a discount. Didn’t buy anything.

Drive home he starts apologizing out of nowhere..i thought it was because of the bad date.

Until the smell hits me.

He passed gas and i had to legit pull over and roll the windows down a while.

– Moth-Seraph

7. Belly button boy

I went over to a boys apartment I had hung out with a few times already to watch a movie.

In the middle of the movie he stuck his finger in my belly button. We weren’t even cuddling. Just randomly turns towards me and puts his finger in my belly button.

I said to him “get your finger out of my bully button?” To which he responded by making a weird noise similar to an adult using baby talk and saying coo coo to a baby and wiggled his finger still inside my belly button.

I left immediately, never talked to him again, and my friends still refer to the situation as belly button boy.

– ab_1999

8. “Just ate his apple and farted”

We met at a trailhead to take a walk.

He started farting right away.

Then he opened his backpack and got an apple. He proceeded to eat the apple. Didn’t offer me an apple.

Just ate his apple and farted.

– Goodygumdops

9. The recovery

Reposting my first reddit comment from 11 years ago: I wasn’t feeling great, but decided to meet anyway. We met at a Belgian beer bar. She was gorgeous, fun, and totally in to me. I felt a gas pain, so I leaned forward slightly to quietly relieve the pressure. I completely and explosively s**t myself. The odor was immediate.

I excused myself to the bathroom, but the damage was too great. I walked out of the bathroom, muddy-panted, out of the bar, and boarded the train for home

The date was nothing, compared to the horror of the following three weeks, recovering from E-coli.

– jeremylee

10. The dress code

On one date I showed up at her parents house to pick her up, thinking we we’re going for drinks in the neighbourhood. She opens up the door wearing sweatpants, trainers and a hoody as if she just got back from football practice. I was pretty well dressed so she decided to change into something else.

She says I can just wait in the living room with her parents. Not that bad, we have some small talk and I expect to be leaving soon anyways.

She then shows up wearing the next less than casual outfit and sits down in the living room as well, saying nothing she just gets on her phone… she’s doing nothing but texting whilst I’m left talking with her parents (didn’t expect a date with them).

At this point I don’t know what to expect anymore, luckily I was able to convince her to go out after a bit and we end up having drinks… all in all she wasn’t my type, definitely after that date.

– Pleasework94

11. The last hurrah

My wife wanted to plan our 13th wedding anniversary. I was excited because usually I plan it. She bought us some new disc golf discs and after a quick supper we went to play. We hadn’t played in forever. We were laughing and I had a great time.

She served me with divorce papers and told me that date was a test to see if she still had feelings for me. I also learned that she was having an affair that started well before our anniversary.

– rmorlock


Went out with a girl when we were probably 13 or 14. We went to see Inception.

She gets up to go to the bathroom, but doesn’t come back for a long time.

Eventually I go look for her, and the guy behind the concession stand looks at me and gives me the most pitying look I’ve ever received, and points around the corner. Where I found her making out with another guy. I should have walked out but instead I went back to my seat to watch the rest of the movie.

She returned and asked me to fill her in on the last hour of INCEPTION OF ALL THE D**N MOVIES TO MISS THE MIDDLE OF. Also, because that wasn’t enough, after the movie, I wasn’t sure what bus to take home, and she pointed me to the wrong bus (I don’t think this was intentional, they were right next to each other) and I wound up in a part of the city I’d never been in before.

– DrVonPretzel

13. The remodel

Tinder date. She looked nothing like her picture while not ugly just completely different. Picked the worst restaurant in town which I looked past because everyone has different taste.

We came back to my house and complained about not showing affection or touching her so I started touching her and then got mad about ohhh wanting a hook up which I didn’t, but the final straw was when she decided she didn’t like my house which I had just bought and was Proud of.

She immediately wanted to go to home depot to buy stuff to start remodeling. It was by far my worst and weirdest date and I hope she found a house to remodel

– ahe_243

14. You sound like my grandma

In college, I hit it off with a girl and agreed to go on a first date to a school hockey game. When I met her there, I realized I had forgotten my wallet, so I had to borrow $5 from her to pay for my ticket. Not a great start, and I could tell I had dug myself an early hole. Then, once we sat down, we realized that neither of us liked hockey at all. I have no idea why we agreed to meet there, but we were both totally uninterested in the game. So we started talking about other things we were into, and I mentioned that I liked board games. She said, “You sound like my grandma.”

At that point it was clear that neither of us were into this at all, but it was the first period of a hockey game that she had paid 10 whole dollars for, and neither of us felt right leaving. We sat there and stonily watched the rest of the game. Afterwards, we said, “Let’s hang out sometime,” and then never messaged each other again.

Then, a few semesters later, my friend called me up all excited about a new girl he was dating. He wanted me to come to a get-together at his apartment and meet her. I walk in, and of course he’s sitting on the couch with his arm around the very same hockey-hating girl. I immediately grabbed my wallet, handed her $5, and said, “Thank God! I’ve been looking for you for two years!” She laughed, and things went all right after that.

– ManateeSheriff

15. Have a nice life

First date after my divorce. She was nothing like her profile picture and just a horrible person. But that not the fun bit. She stalked me to my work van after the date and took down my phone number. On the way home she asked if I would come back and see her, said thanks but no thanks and have a nice life. In the proceeding days I received numerous texts and phone calls from her and had to have her number blocked by my phone provider.

On new years day at 4am I receive a call …… from her ex husband asking what was wrong with her?

That she is a good person etc. etc. Turns out they went out on NYE and got s**t faced together and decided to all me. I hung up only for then to keep calling me back. Ended up turning my phone off. Woke around 7. Turned my phone on and I had received 20+ voice recordings that were getting more and more threatening, on the last one I could hear them in a car saying they were coming over to get me.

Spoke to my neighbour who gets up early and had gone for a run and he told me there were a couple being arrested around the corner from our place drunk as h**l who had hit a light pole. Scary thing is I had my 2 daughters with me that night.

– Krustyliciousness

16. The reconnaissance mission

Met a girl online, everything seemed okay and the conversations were good so a few days later we decided to meet for coffee and go for dinner later.

I show up to the cafe about 45 minutes early and order a coffee, intending to read for a bit. While I’m reading I notice an older fellow staring and taking far too much interest in me before leaving. Odd, but okay. Continue to read until about 10 till meet up when I text the girl that I’m already at the cafe.

Shortly after, the odd older fellow comes back in one entrance, and this sets off my Spidey sense so I’m making my way to the other entrance when my date catches my arm to say hi. I tell her we should step out for a minute, getting a bad vibe from this guy, she asks which one, so I describe him.

It’s her godd**n dad, doing advanced recon for her dates at 24 years old. I was a bit sketched out at that, but thought maybe she had some bad dating history that possibly made sense. I meet her dad, he says they wanted to make sure I was who I said I was and to enjoy the date. He leaves and she says being an only child has its downsides. Makes enough sense, we get coffee and chat for a bit, walk in a nearby park and decide where to go for dinner. We get to my car and she asks if I could take her home to grab a jacket before dinner, no big deal.

We arrive at her place (lives with parents) and I talk to her mom and dad while the date grabs a jacket. They seem nice, but overbearing parents. Date calls me back to her room to meet her cat, and the entire time I’m meeting her cat, the parents are hawking nearby obviously eavesdropping and it’s obvious the date is dragging her feet for some reason. I said something about getting out to dinner before the rush and her parents who “happened” to be walking by ask where we were going before they start a dialog on local restaurants, which pivots to ordering delivery/carryout and how we should just do dinner together at their place.

I told them no offense, but I’d greatly prefer to dine in someplace relaxed and get to know their daughter. They seem really resistant to this, I’m agitated, and ask if this is how her dates normally go. They said “no, normally we don’t let her go out with men, but you passed the background check and your messages to her made you seem nice like you’d have dinner with us”

I was flabbergasted, they ran a background check on me, read our exchanges online as well as the advanced recon, and expected me to have dinner with 2 additional people I hardly knew when I was expecting a date. I told them that will absolutely not work for me, and that they are being extremely over the top with their expectations and precautions. I left.

Later received a torrent of text messages and calls to the general sentiment of you were supposed to be better than this. I don’t respond for a day before telling her/them this is not normal or healthy, I refuse to be any part of it and will be blocking their number and filing restraining orders if I find them lurking around.

– Predditor_drone

17. The undertaker

It was with an undertaker’s assistant. He’d circle every topic of conversation back to corpses.

Me: “So, do you know what you’re gonna order?”

Him: “Well I was thinking the steak, but I had eaten steak when we got the river guy in, and now it makes me feel queasy.”

I ended up leaving after half an hour.

– CrazySnekGirl

18. Making the climb

Matched with a cute girl, she likes to climb, we have good chat, great. Let’s go and do some top rope and hang out. But she doesn’t have a car, so I need to pick her up, 30min off route. I’m not thrilled but whatever.

Meet her and, well, it’s not her. Or it is her from the profile, but maybe from 5-8 years and a kid ago? I’m tempted to call it off but I’m too much of a softie, and she says she made cookies. I love cookies. We head off to the small local cliff.

We arrive, walk the ten minute approach, the conversation is still fine but I’m wary now. I resolve to just have a nice time and have some fun, and just learn from the experience. She’s perfectly nice but I’m seeing red flags.

At the crag she says she borrowed her friend’s shoes and isn’t sure they’ll fit. Same with the harness. Uh oh.

Well they do fit, yay!, so I rig the anchor and we start climbing on a nice 5.6 (easy) for a warm up. Except that she can’t climb. Fine, okay, whatever. We’re still chatting as she works on the off-ground move, and then just bursts into tears.

Turns out that it’s HER SISTER’S DATING PROFILE and that’s who she borrowed the stuff from, and that HER HUSBAND DOESN’T KNOW SHE’S ON DATING APPS. I find all of this out amid tears and so does everyone else there who can overheat it.

Some very awkward talk therapy later, I drop her back at her house (is it her house? Is it her neighbour’s house so that hubby doesn’t see?) and she leaves me the cookies as an apology.

And they were store bought.

– Kilbourne

19. The other woman

I went to a new years eve party with a guy I had been chatting with for months. When we get there his friends asks him where his girlfriend is, and they were not referring to me. I went out for a smoke at that point and he went after, saying she was boring and he was gonna break up with her.

I didn’t hang out with him for the rest of the night.

I guess I should thank him because I hooked up with the party host instead and we’ve been together for 7 years.

– mayneffs

20. Just a heads up

I told my date before we went out that I was divorced, just as a heads up.

She pried for more information and I tell her my wife had an affair.

She starts joking about it then asks to see a picture of my ex and the guy she left me for.

Then she called her affair partner cute.

Oh and she spent the other part of the date calling me fat.

– MayorCobblepot

21. The whole story

She started talking about her life story from childhood to that day. Year by year.. with every single traumatic story and emotions.

That was our first ever date and she didn’t even let me speak for that duration.

I was like “oh okay she is now talking about highschool 6 more years left, hold tight”

– Paranoides

22. The blind (drunk) date

Got set up on a blind date once between mutual friends. She shows up to the restaurant already a little tipsy, orders multiple appetizers and only takes like one or two bites from each one.

Then she proceeds to order 3 or 4 more drinks and is visibly drunk at this point. She gets up and says she’s going to the bathroom and staggers off.

About 15-20 minutes go by so I try to call her several times but no answer. Finally I decide to pay the check and just leave.

About 2 hours later I’m sitting at home and I get a call from an unknown number. It’s the police department. She was picked up on a DUI on her way home after she ditched me and gave the cops my number to see if I could go bail her out!

– mox44ah

23. Nothing but the tooth

I went on a date with a guy who picked me up and said he just had to swing by his work before we went to the restaurant. No problem. He works in a dental office as an assistant, so he invites me into his work, the office is clearly closed and no-one is there, and all the lights are off. Okay a bit weird but maybe he just forgot something really important that can’t wait until tomorrow morning to pick up?

Nope, he’s going to the medicine cabinets and taking out a few bottles of ketamine.

Okay. I’m now an accessory to theft of dental anaesthesia.

There was no second date.

– DreyaNova

24. The chat up

We went to dinner and he started chatting up the waitress. Like interrupting me every time the waitress came over and talking to her for a few minutes instead.

After a couple times I just pulled my phone out and started scrolling through reddit and he complained when he noticed I was on my phone. Cue a lecture about my generation. (he was like 6 years older than me, iirc)

Then he got mad when I wouldn’t suck his d**k in the parking lot. I ended up going back inside the restaurant and calling a friend to pick me up. Dudes car was still sitting there when I left. F**k you Jason.

– gengarsnightmares

25. “They”

Showed up to a tinder date where we agreed but she wasn’t there. Texted and she said “they” were around the corner. Come to find her(mid 20s divorced socialite) and her friend (mid 40s sales man) had been drinking all day and were proper s**t faced.

Proceeded to join them at the table where she proceeded to talk about the married guy at the next table and kept walking by and dropping things so she could bend over in front of him.

Then some racist talk and some cocaine use (them not me). And then they decided, mercifully to ditch me because I was no fun.

– IncrediblyShinyShart

26. The theft

Came out from a movie, late at night, and date’s Camaro was stolen. Apparently, he called his WIFE (that I did not know he had) and let her know where he was and what happened.

She showed up and realized he was on a date!

She started chasing ME around the parking lot telling me she was going to kill me. Saved by the cops who showed up just in time to take the auto theft report.


27. The big quiz

I was brought up in Poland by Polish parents (university professors) , went to a Polish school, Polish university etc.

Then I had a date with an American man whose grandmother was Polish. He grilled me on the language and criticized my pronunciation and corrected my grammar.

This from a guy whose Polish vocabulary was maybe 100 words.

He told me I speak like a peasant.

– fantazja1

28. Very pricey

Was on a first date. Went to the bathroom, asked the guy to watch my coat. Came back and my coat was gone. It had my cellphone, wallet and keys in it.

Guy was too busy chatting up the bartender, hadn’t even seen the guy take it.

We had to uber back to his house so he could get his truck and drive me home. Had to wake my roommates up to let me in, had no ID, cash or way of contacting anyone for days.

Ended up tracking down the guy who stole it but only got back my phone, he threw out my wallet, keys (with fob on it) and coat.

Guy I was on the date with never contacted me again! Most expensive worst first date ever!

– confusedthrwawayxx

29. Sucks to suck

I had a date with a guy who spent the entire date whining about how much ‘this’ or ‘that’ sucked. Everything sucked. The food, the wait staff, the movie, the fact that I took my own garbage to the garbage can after the movie, and most of all, the night shift computer people he saw who hung around the outside of their office, smoking (he complained about their high salaries).

I pointed out that I was one of those computer people (no, I didn’t mention how much I made), and that was the LAST date I ever went on with him.

I never talked to him again.

– Ladyjaneinmd

30. The lies will find you

When I was in college many years ago, before the advancement of cell phones and social media, I was chatting with a girl I met on a BBS who lived on Long Island, NY. I was 18 at the time, but lied and said I was 22 because she said she was 25.

We spent a few weeks emailing each other, as well as calling each other. We even exchanged pics.

When we finally met up, things blew up. Turns out we both lied about our ages: She was really 33, and lied because she thought she looked younger. She admitted she sent a college photo to me.

We still had dinner together, but it was awkward as he**. We never spoke again.

– 4EVRGamer

Just remember: there never has to be a second date.

What’s your worst date story?

Tell us in the comments.