People Share Stories of the Worst Dates They Have Ever Been On


The dating world is very tricky business. And with the rise of dating apps like Tinder, Bumble and hitch, things just got a lot more complicated.

You may have been on some great dates in your life, but for every good one, you probably have had five awful ones. Thinking back on all those horribly awkward dates can be a scary prospect, so we figured that best way to get over them is to replace those memories with the hilarious stories of other peoples horrible dating experiences.

So, in the name of mental health repair, we ask people to share stories of the worst dates of their lives. Some of these are absolutely ridiculous.

Start the article by pressing the button below the image

1. This guy was definitely on something


It was a blind date. We met up at a coffee shop close to our university. He was definitely under the influence of something, and it was hard to get a normal conversation going. He just kept telling me I was as beautiful as the brick wall we were sitting next to, and that my skin looked soft enough to be made into a nice silky robe.

It was really weird and awkward, so I excused myself for the bathroom and decided to just leave him (including the bill). The date lasted maximum 10 minutes and that was the worst and longest 10 minutes of my life.

2. I unknowingly dated my cousin


I was asked out by a cute coworker who was from a neighboring town. The date was incredible! He was smart, funny and probably the most attractive guy I’ve ever met. When he dropped me off, he was kind enough to come inside to meet my parents. My grandma happened to be there and said, ‘Eric, it’s so great to see you, I just had coffee with your mom.’

Me: “Grandma, how do you know Eric?”

Grandma: “Sweetheart. He’s your cousin.”

After that we hung out as friends and swore we’d never tell anyone at work that we totally dodged a bullet.

3. I’m dating a witch!


I met this drop dead gorgeous girl at the mall and mustered up the courage to ask her out (I’m usually a pretty shy guy). So we’re sitting at bar at a local restaurant, and she informs me that she is a witch, and that she had made her last boyfriend love her by casting a spell on him. She was even nice enough to tell me how the spell works, “I took a vial of my period blood and poured it into his wine, and tricked him into drinking it.”

“Now he’s mine forever” she told me. She went on to say that it turned out she didn’t really love him, but because of her spell, he would love her forever. She claimed he was still desperately in love with her even though she had dumped him.

4. This guy offered me “his seed” on our first date


A few years ago I went on a date with a retired athlete. I was 27 at the time and didn’t have any children. For some reason he thought this was weird and told me that something must be wrong with me if no guy had given me their seed by now. He went on and on about my “biological clock ticking.”

I remained silent the whole time because I didn’t know how to react. After a minute of awkward silence, he asked me if I was ovulating because he’d be willing to give me a child if I need. I’m happy to say we never spoke again after that miserable date.

5. The one who was NOT as good as advertised


I met a girl online, but she didn’t have any pictures of herself. She described herself as a 24-year old blonde with blue eyes and an “athletic build.” I really wanted to see her so I asked her out. I even let her choose the place so she would feel special.

I arrived at the restaurant with a big smile on my face, but I soon found out this “blonde bombshell” was actually 47-years-old and had three children with three different men. Needless to say we never talked again and I no longer find dates online.

6. The epic first date fart


It was my third week of college and I really hit it off with this girl in one of my classes. We decided to meet up for dinner one night in the middle of the week. I got there a few minutes before she did, and when she came in and sat down, she farted really loud. Like unavoidably loud. She excused herself to go to the bathroom and never came back.

I’m now a senior in college. I’ve seen her around campus a bunch over the years and we haven’t talked since that day.

7. When your Nails Attracts Him More


I was on a Tinder date with this guy and he was super awkward. It was weird. He tried to hold my hand and noticed I had acrylic nails on. So he picks up my hand and says “they’re so sharp like a cat…. scratch me”.  And he insisted I do it, so I just scratched the back of his hand and quickly made my escape.

Immediately after the date, I spent 20 minutes complaining via Chat App about how bad the date was. I thought I was talking to my friend with the same name as my date. It was my date and not my friend. I felt bad about it for weeks.

8. “You’re much prettier than his girlfriend”


I went on a date with this guy I met at a party. He invited me to wedding reception, and I said yes of course. When we arrived at the place, his relatives were there including his parents, and introduced me to them. Then his mom told me “You’re much prettier than his girlfriend.”

It was the only time I’ve ever thought about faking a phone call and pretend that there’s an “emergency” so I can leave.

9. He Wanted a Reimbursement for His Drink


Over coffee, he told me he was married but that his wife was “flexible”. He acted genuinely surprised that this wasn’t fine with me. It was really awkward.

The next day I told him I wasn’t interested in seeing him anymore, then he asked me for a refund of the drink I offered to pay for but he insisted on buying.


10. The Guy with a Secret Hole


Met a guy who grabbed my hands and looked me dead in the eyes. Told me he had to tell me something so I wouldn’t freak if things got serious. He then proceeded to tell me how they screwed up his Circumcision. That he had two holes in the skin under the head that you could fit a pen into.

I don’t know if it was like you could fit in one hole and out the other or two separate holes the size of a pen.  I’ve wondered for years. How did he know a pen would fit unless he stuck one in. I was too blindsided at the time to ask. Never talked to him again.


11. Do you believe in Dinosaurs?


I met a guy online and agreed to meet somewhere. When talking about weird things that we believed in he proceeded to tell me dinosaurs are still alive and walk beneath the earth and that’s what causes earthquake.

He was dead serious too. He was very confused why I didn’t want to see him again.

12. The Killer Smile


We’d matched on Tinder and arranged to meet. We’d chatted a fair bit and he seemed like a nice guy and pretty funny, but we’d not gone as far as exchanging Facebook names or Instagram. Looking back, this was my first rookie mistake.

We went to dinner – never a good move on a first date as it takes a minimum of an hour and a half – but I still turned up excited to meet him.

So we finally met. He smiled at me and I was completely taken aback – he had no teeth! I awkwardly sat through one very hurried course before rushing home to check his Tinder profile again. He hadn’t been smiling with his mouth open in any of them.

13. Some Men Talk Too Much on Dates


Meet a guy from an online dating site. He seemed nice, but never stopped talking. After interrupting me for the 3rd or 4th time, I finally ask him “Do you want to hear anything I have to say?” He apologized profusely, said “You’re right, I’m so sorry!” and pulls out a pad of paper and a pen.

He then jots notes as I’m telling him about myself and whatnot. I finally ask him what he’s doing and he says “Oh, I’m writing down things I want to tell you when it’s my turn to talk again.”

14. He Gave Me a Poop Soup


I once went on a date with a guy who spilled a giant cup of ice water all over me at the restaurant. After dinner we go to my place so I can change into dry clothes. He uses my bathroom. After taking way too long he asked me through the door for some towels — he clogged my toilet with his manturds and then got his poop soup all over my bathroom floor.

Oh, and I realized at one point he was wearing a toupee because he’s balding, which he was super weirdly sensitive about.

15. Dating with Roaches


Went out a bunch of times with this awesome girl I met through a friend. Smart, strong opinions and a pretty cool free way of thinking and living. She wanted to show me a place where she used to go to drink and dance. So we did. We arrived there, sat and asked for beers.

Five minutes in, I feel something on my back. I slap it with my hand and looked at the ground.. It was a Cockroach! Two minutes later, there is a cockroach going up her leg to which she yelled, but we kept drinking. Suddenly we look around and there are cockroaches going up the walls and tables of everyone. It was like a invasion. The cockroaches were everywhere. Every hole, every possible space on the ground. Disgusting.

16.  He’s asking a Different Mode of Payment


I went out for dinner and a movie with a guy. I tried to chip in money during both, but he insisted that he cover it all. At the end of the night, we’re sitting in his car in the parking lot of the restaurant we had just eaten at, and he asked me to touch his “down there” and said “I mean, I bought you dinner and took you to a movie, it’s the least you can do”.

Thankfully I lived nearby, I hopped out and walked home.

17. Aliens, aliens, aliens!


Dating is never easy but it’s even more difficult when you wind up on a date with someone who believes in aliens and only wants to talk about their alien obsession all night.

He said that when it rains, it’s because the aliens are sad, and if there’s a thunder and lightning, it means that aliens are really mad or just bowling.

Let’s just say I was really happy when the bar closed.

18. He Wanted to Show Me His Pee Trick!


A guy took me to dinner but forgot to make reservations, so we couldn’t get a table. He then suggested that we should go to a different place where he proceeds to drink way too much.

On the our way home, he asks me to get out two stops before my actual station to watch him pee into the train tracks.

19. The Unknown Girl


I met a girl for a blind date once. She seemed a little flustered at first, and I thought that was a little weird. She didn’t say a single word throughout dinner, finished her meal and walked out. I then checked my phone and there was a message from the girl saying she couldn’t make it tonight.

Who the heck did I just eat with?!!

20. Puppy Trumpet


I met a guy online and we went to the movies on our first date. At the end of the night acted like he was going in for a kiss, but instead he put his whole mouth over my nose and blew into it.

He laughed so hard and said he does this to his dogs and calls it a “puppy trumpet”. After that date, I never contact him again.

21. First Date Disaster


I’m a big strong guy but I’m also a baby when it comes to horror films and such. However this girl wanted to go see a horror movie as our first date and I was willing to act tough. I tried but I just couldn’t handle jump-scares. I’m fine with disgusting things, but don’t you try to scare me. Long story short, a jump-scare happened and I spilled a good portion of my cola onto her white shirt.

For a moment, I hoped that I would just apologize and few weeks later we would just laugh about it and have it as our cute story. Well, she had a different opinion, she changed seats, finished the movie, let me drive her home without saying a word and didn’t respond to my texts anymore.

22. What A Coincidence


In college, a friend of mine set me up on a blind date. I wasn’t in a great mood at that time because I had received a traffic ticket a few hours before.

When I arrived at the meeting place, my day got worse when my blind date turned out to be the cop who gave me the ticket. I immediately left him and never respond to his messages again.

23. That’s Cringeworthy, Girl


Once, I met a girl through Tinder, and she was beautiful and interesting. She was a background actress. As I approached where we were meeting up, she called me to ask if I was on my way and explained that she asked to meet here just in case I was a serial killer or something.

Then during the date, she started calling me her boyfriend, and at the end of the date she told me she loved me and that I was an angel sent by God to her. Maybe it’s not funny, but it was definitely cringe-worthy. We actually dated for a few weeks.. What? I said she was beautiful.

24. I’ll take an assist on that!


So there was this really sweet girl I had been interested in but I was too afraid to ask out. One day, I finally had the guts to ask her out. Surprisingly, she said YES! The next day, we went out to eat. I was so ashamed when I realized I forgot my wallet. So she paid for me.

Then we went to a party at a mutual friend’s house where I got mistakenly got black-out drunk and passed out. My buddy was at that party and now the two have them have been dating for 3 years. Still don’t know what happened that night.


25. Humor Should Match Too!


I once went on a date with a guy who talked a lot about his pet snake. He then followed up talking about it by saying, ‘Sometimes I get my snake out at parties and let people play with it.’

He got really confused when I burst out into surprised, uncontrollable laughter. I guess our senses of humor didn’t align. Also ew, who has a pet snake. Even If you do have a pet snake, don’t talk about it on a first date, weirdo.

26. Get the Food out of your Teeth, please?


I went on a blind date a couple of months ago and the guy was totally lovely, really friendly and likable. The only bad thing is that he had pieces of food stuck between his teeth the whole time and I don’t have the courage to tell it to him.

This doesn’t seem too big of a deal, but trust me, there was a LOT of food in there. It was un-natural. It got really awkward, very quickly and I just couldn’t get past it.

27. Abort Mission! She has a Boyfriend!


A friend of mine set me up with a girl he knew. She was cute, funny, smart, everything you hope for in a blind first date. After spending a good part of the day with her, we end up at this frozen yogurt spot. We talk for a bit and she mentions how much fun she had today. Then she says how much her boyfriend would like this spot and that we should all hang out next week.

I didn’t see that coming. I searched her on Facebook after the “date” and found out that she had been dating this dude for a couple years. Yes, she did indeed have a boyfriend. Never asked that friend to set me up ever again.


28. Wrong Sent Messages isn’t Bad at All


I’d only met someone from Tinder once (he was a bouncer at a club). First of all, he showed up to our date unfashionably late by 30 minutes. He apologized, gave me some bogus excuse and we ordered our food.

While waiting, he checks his phone and he accidentally texted me something along the lines of “Sorry babe, I’m at church so I will be late” then had the nerve to say he meant to send it to his sister.

29. An Unexpected “Meet the Dad” Moment


Met a girl in a bar. Bought her a drink. Agreed to meet again. I went to her house to pick her up and take her to the movies. During the movie, she kept looking at the person behind her.

Turns out, it was her Dad sitting behind us the entire time with an angry-look. He then yelled at me and asked “What the F- do you want with my daughter?!” I quickly left and renamed her number as DO NOT ANSWER.


30. “She’s Not Even that Pretty”


It was a blind date and to my surprise, he was kinda cute. We talked about random stuff, and everything went fine until his phone kept ringing. I told him to answer the call, maybe it’s something important. He said no worries, it’s just his ex-girlfriend.

After like 10 missed calls, he finally answered and then ended the call with “She’s not even that pretty” and “I love you too”.

31. The Date that Ended Before it Started


Not actually a date, but it was the worst pre-date ever. So I met this guy online, and he asked me if I like heels and when I said yes, he then asked if I would wear them to our date along with high-waist jeans, full face of makeup, and lip gloss like “he likes”.

It wasn’t a big deal until he followed up with “Are you gonna look good for me? If not, then forget about me. You aren’t worth my time.” Ok then, date cancelled!


32. A Budget Date


I went on a date with this dude who asked me out. We’re seated, he sees the prices of the menu and goes “this is too expensive,” waits for the free water and stuff they give out, takes the free stuff and is like “Ok, let’s go somewhere else.” I have no choice so whatever.

He then takes me to another restaurant, and told me I couldn’t order anything more than $10 off the menu. I couldn’t believe it so I stopped talking to him and left. He then walks ahead of me and doesn’t even check to see if I’m safe.


33. My Pyramid Scheme “Date”


Met a guy via an online dating site. He corresponded with me daily for weeks and seemed pretty interested. After few weeks of chatting everyday, he invited me to hang out. It was our first date so I made sure that I look presentable from head to foot. I spent hours just to look beautiful so he will not be disappointed.

When I walk in to the door, I was like OK, maybe this is some kinda party/kick back and I’m just early. So I sit down. Then he turned the TV on and it actually turned out to be a MLM/Pyramid Scheme recruitment meeting.


34. A Date in the ER with Michael Jackson


So my date shows up with a friend who is dressed like Michael Jackson. On our way to the car, his friend drops a bottle & a shard of glass pops into my date’s eye. Cut to the Emergency Room. Me and his friend are in the waiting room.

After like 20 minutes of waiting, his friend gets up and proceeds to put on a full concert of Michael Jackson tunes. It was the most confusing 4 hours of my life.


35. I Unknowingly Dated A Guy with a Girlfriend


There was this guy who always messaged me how much he liked me. He asked me out on a date. I was single so I agreed. Long story short, I ended up having to pay the whole tab (cause he forgot his card) and drive. Ok, no problem.

Then during the movie, his girlfriend found my Instagram and messaged me telling me how they been dating for 3 years & he always does things like this. I was shook! I immediately got up and left.


36. He Let Me Pay for Everything!


I once went on a date with a guy, and while we were driving to dinner we got a speeding ticket. He asked me to pay for the ticket, because I was distracting him, and then took me to dinner where he made me foot the bill.

After that he took me to a nightclub, where he told me about other girls he brought there. I made him take me home shortly after that and told him to forget my number.


37. She Walked Out after Seeing Me


So I met this girl on the internet and she seemed really nice and down-to-earth. We had a lot in common including our hobbies and politics and stuff like that, so I was thinking we might hit it off.

We agree to meet up in person at Coffee place. Now bear in mind that I’m not super attractive so up to this point she hasn’t seen any pictures of me, instead we have pre-arranged recognition signals. She walks in the door and I spot her by her clothing instantly, and start waving. She gets this sort of uncertain look on her face and walks over and says ‘Sam?’ and when I say yes she just says, ‘Haha.. No!’ and walks out. It felt pretty bad.


38. Mind Your Date, Not Your Phone


I met this girl online and asked her out. She suggested that we should go bowling and that it would be very fun! So I went and picked the girl up, and took her to a bowling alley. She was texting the entire time we were there. She said her sister texted her that their puppy barked for the first time and she’s just asking for a video of the puppy barking, and that I should wait.

Cool I can respect that. But when I have to spend more than an hour with someone I barely know and I can’t talk with you for more than 10 seconds without you looking at your phone, it’s really bad. Also, we weren’t able to bowl because she wanted to go home to see their puppy barking in person.

39. The Best Gentleman Ever!


I hadn’t seen the guy in years, but we’d had a few dates back in the day and stayed friends on Facebook. I’d just been dumped so when he asked me to go for a drink, I said yes. We were only meant to have a quick coffee but he immediately launched into a rant about how terrible his life was now. He’d recently broken his leg, which got infected. There was pus, and showed it to me. It was rancid and smelled awful.

Then he made me go to a store with him to help him carry his groceries. Needless to say I wish I’d never met up with him.

40. I’m done paying your cab fare. Bye!


I’d been on two dates with this guy that I’d met online. When we first started speaking, I initially thought that I had hit the jackpot: he had immaculate grammar when texting, was really good-looking and seemed totally perfect. We got on really well during our first date, and I didn’t even mind when he insisted that we take turns buying drinks.

But then when it was time to leave, I ordered a Taxi to take me home, and he got in, asking if he could share the taxi (even though we live nowhere near each other). When we pulled up to his flat, he jumped out without offering to pay for his fare. At first, I wasn’t that put off – until the same thing happened on date number two! I mean, I’m all for going Dutch, but when I’m having to pay for YOUR cab home – boy bye.

41. ‘Do you think this girl is right for you?’


On our three-hour drive to a food and wine festival, I stopped for food, leaving my phone in the car with my date. My cousin texted me, ‘Do you think this girl is right for you?’

My date took my phone, read the message and asked the same question in an angry tone. I was so put off by the invasion of my privacy I was just honest and said that she probably wasn’t. The next three hours in the car, we drove in absolute silence.

42. He had his own”Appointments”


Went to the zoo with a guy, we rushed through it and he wouldn’t let me see much of anything because he had a hair appointment he just had to keep. He was getting his remaining hair “frosted” which I thought was very weird. Does he think he’s in a boy band from 15 years ago?

Second and last date, he left me sitting alone at a table in the park for around a half an hour because he saw a tree he simply “had” to meditate under. Alone.

No longer dating men with frosted tips.

43. Strip Club on First Date? Nah!


I was out on a date with a guy who said he had no money because he forgot to bring his wallet and borrowed $10 to buy a drink at a convenient store.

He came back with a scratch-off, won $60 and took me home since I wouldn’t go to the strip club with “his winnings”. To make things worse, he didn’t give my $10 back.

44. She just need “a little help”


The time I met my date at her place and she started talking about making a “donation” to help her out with rent and so on. She was even nice enough to point out where the closest ATM was.  She also made it abundantly clear that she WAS NOT a “working girl” and simply needed “a little help.”

Nope, nope, nope, nope. BIG-TIME pass baby-doll. As I left, I started to wonder how many guys she’d done that to and how much money she’s secured from those dummies.

45. He is Feeling Himself Too Much


A guy I met online who was so full of himself, there was no room for me at the table. He asked me if I liked his watch, then told me it was a $20,000 birthday gift to himself. He also told me he could pleasure himself better than any woman could.

At one point, he even asked the elderly women sitting next to us if we made an attractive couple. They said yes. His response? “That’s right ladies, you can buy me online!” I was so embarrassed, apologized to them, and said he was right—you can buy any kind of crap online.

46. Slow down it’s our First Date


I went on a first date with a guy and he asked me what temple I wanted to get married in, my two favorite colors and my favorite season.  Then we went to the mall before our movie and he went ring shopping and bought a ring for our wedding.

The date lasted SIX HOURS and I did not know what to do to stop it. Then, when he took me back home, and said “Please don’t forget to text me tonight about your dream wedding so we can plan it next week”. I’m done with online dating now.

47. You had fun, Really?


I ordered a steak for lunch and he tells me I shouldn’t be eating steak, I should get a salad so I don’t get fat. Freakin’ serious? Then we went across the street to a bar where he totally ignored me and started talking to a guy about baseball. Like, COMPLETELY ignored me.

So I grabbed my keys and said, ‘I’ve got to use the bathroom, I’ll be right back,’ and Irish goodbye’d him. The next day he texted me, “I had fun. We should go out again sometime.” LIKE YOU DIDN’T NOTICE I WENT TO THE BATHROOM AND NEVER CAME BACK!?!?

48. A Not-So-Good Greeting from His Dog


When I was 24, a guy took me home to meet his mother on our first date. I thought we were going for coffee. We did… At his mother’s house. When I walked in, his dog greeted us very enthusiastically and proceeded to pee on my shoes.

to be honest that wasn’t even the worst part of the date. His mother sat with us the whole time. It was SO AWKWARD. Needless to say we did not have a second date.

49. Mansplaining at its Finest


My Date and I went to dinner. He comments on me ordering pizza in an Italian restaurant. He comments on me eating pizza with knife and fork. He comments on me not wearing enough make-up. I politely ask about his work. He explains what he does as if he’s talking to a 4 year old, even though he knows I’m getting two master degrees and already have a degree in Biology.

Throughout the date, he kept explaining stuff to me as if I’m in kindergarten. Doesn’t ask anything about me and goes on long monologues about himself. I decline getting another drink and leave. Dodge his kiss and give him a peck on the cheek instead. On my way home, I get a text asking if I’m sure I don’t want a kiss.

50. I just wanted to have coffee?


I recently signed up for a dating site and had my first date. Let’s just call her Caitlyn, she seemed nice enough, and attractive, but on the actual date all she wanted to discuss was politics. She was discussing politics the whole time, like non-stop, and I don’t even have the chance to talk.

I have nothing against anyone interested in politics, I’m just not into debating national policy on a first date.

Kat Begonja

Kat Begonja

Lover of animals, writing and all things Croatian!

Leave a Reply

Your email address will not be published. Required fields are marked *

Want to Learn Ways to Make & Save Extra Money?

Sign up for Free Updates: