Skip Nav
Movie Trailers
These 2016 Romance Movies Are Equal Parts Sweet and Steamy
Wedding
44 Vintage-Inspired Engagement Rings
Kate Middleton
The World's Most Iconic Engagement Rings

Do Tell: What Was the Worst Date You Ever Had?

Bad date stories are often funny after the fact, but when you're out with someone who's making you annoyed you even got dolled up and scheduled time for them, it can be depressing.

We've all had boring dates, but some stand out for their sheer weirdness. I am a freak magnet, so I have my fair share of weird dating tales. There was the guy who took his shoes off as soon as he sat down, the guy who took his false front teeth out for show-and-tell (he'd been a boxer), and then there was the charming dude who insisted the sushi chef at the bar speak Japanese with him, even though he spoke perfect English. After a few rounds of coercion, the chef finally said, "Will you just shut up and order?" Naturally, those first dates were also the last.

If you're single, dating can be an occupational hazard. What was the worst date you ever had?

Image Source: Getty
Around The Web
Disney Date Ideas
Romantic Date Ideas
Amy Schumer's Best Sketches | Videos
Books For Women in Their 20s
Harry Potter Fan Art
Kaitlyn Bristowe and Shawn Booth Interview
Signs You've Found Your Soul Mate

POPSUGAR, the #1 independent media and technology company for women. Where more than 75 million women go for original, inspirational content that feeds their passions and interests.

Join The Conversation
emmebeth emmebeth 6 years
Chouette4u- That is so hilariously inappropriate. What a whack job.
dikke-kus dikke-kus 6 years
Bad dates can be a hoot. My sister's was my favorite one. One time she went out on a date and then during a quiet chat outside he suddenly started climbing up a tree. Just climbed it. I asked her how old he was for Pete's sake. I think he was 19 or so. It was the same guy who bragged about running from the police on foot through some woods after a big car chase and not getting caught. Hilarious.
MissSushi MissSushi 6 years
I really only have one good bad date, kinda long becuase im too nice. I knew a guy who kept asking me out, he was interesting and a nice guy who I worked with, but we were working seroius overtime at work and I was just really bushed from 16 hour days in an inbound call center.. So, he keeps asking me to let him take me to dinner before an upcoming pool party with other coworkers, and I finally agreed. He picked me up on time, was clean, smelled nice, etc. The conversation was going fairly well, and then we pulled up to Subway. Now, im not so snubby to look down on Subway, but after all of the talking and the requests and the dinner invites, I just sort of assumed it would at least be a resturant and not fast food.. So, we go in and he orders the most putrid smelling highly spiced sandwhich I have ever had the misfortune be within 5 miles of. His breath was ruined for the entire night. So, we eat and leave, but seeing as how it was Subway, we had an hour and a half to burn until the pool party later, he asked if i wanted to swing by his friends house. I agreed (no idea why, looking back...) and we showed up at his friends home. Well, his friends parents home, which they were still living at. So we go in and head to their bedroom. Its FILTHY! There are no chairs, just a bed, and theres crap laying everywhere.. it was incredibly awkward for me. They are acting like its perfectly normal to just flop down anywhere, so i walk to the far end of the bed and sit, only to find that the mattress is totally hanging off the side so i sorta slide down and have to plant my feet to sit. So, they start talking familiarly, with no regards to me, all about their future plans. Apparently, they were planning on renting a house all together, my date, his friend, and his pregnant girlfriend. They are going on and on about this "business opportunity" of soap with little toys inside of it. The men kept saying how big it would be becuase kids love toys. OMG it was soo awkward. So, then, my date tells them he's getting a blue pit puppy. I kinda looked at him weird, pits have always been my favorite dog becuase of their sweet loyalty. The pregnant friend was having NONE of htis. She starts shrieking about how dangerous they are, and how he wont have one around her baby, yadda yadda. So, my date then boldly tells them that i (as in me, not him) want one and its half of his house, so thats final. It became readily apparent that he had been listening in on my conversations with my friends at work. stalkkerrrr... We left shortly after the awkward silence. I went to the pool party after figuring i could just ride home with one of my friends afterwards, and becuase honestly, i was DYING to tell them about the date. We get there early and hopped in and I started diving and jumping and such, i love the pool. The host and his girlfriend, were there, but there was about 45 minutes until it officially started. Well, almost everyone ended up noshowing, and I was stuck with pyscho date once i realized the night was a flop. The kicker of the date was when he tried to get me to have sex with him in the pool. Fabulous! I avoided him like the plague and it was a nice eye opener on paying attention to who was near me when i talked about myself.
ladychaos ladychaos 6 years
I went out with a guy to a party last December, and he left me mid-date to go mess with another girl.
nicklover nicklover 6 years
once I went out with this guy. He was very sweet and nice and everything was going well until we ran into his girlfriend.
Marci Marci 6 years
Gee, there are so many to choose from........ I guess I'll go with the guy who got things off on the right foot. He came to pick me up with flowers, pointed me out in a family photo on my wall asking 'who's the pretty girl sitting in front', took me to a really nice restaurant. I was feeling pretty good about things. Then after appetizers, he said he felt close to me and wanted to share some things with me. oooookay........ He proceeds to tell me his hair looks great but he had gotten hair plugs; his teeth had just been bonded, and not to worry; he wouldn't stalk me. beep, beep, beep, beep....warning, warning warning! I got through the meal but knew this guy would be a problem, and he was. That was Saturday night and when I got home from work Monday there were 6 messages from him - sorta like the guy in Swingers who couldn't stop leaving messages for the woman he'd met.
katiekat95 katiekat95 6 years
This is actually a date of mine that was posted on www.myveryworstdate.com After I ended a long relationship, my best friend from college thought it would be a good idea to fix me up with her boyfriend’s childhood buddy because we were both wine connoisseurs. I agreed. The location of our first date was a wine cafe. It did not start well. Within five minutes of the date, he was already pointing out that I had a “terrible habit of biting my nails.” I was troubled by this critique but ignored it and the other small comments that danced on my nerves. After lunch, he suggested a walk. I’d had too many glasses of wine so I agreed even though I knew the date was going nowhere. On route, he asked if I would mind stopping at his old friend’s house for a minute. I didn’t mind especially since he came into town for the specific purpose of our date. We approached the house and rang the bell. An older couple answered the door, which totally confused me. It took me a while to realize that they were his ex-girlfriend’s parents, who clearly were not over my (apparently highly eligible) date. We sat at their outdoor bar (drinking beer mercifully!) for two whole hours discussing how he would one day marry their daughter and how wonderful their relationship had been. I have never felt more uncomfortable in my life. This dude still wants to know why I never called him again.
catita85 catita85 6 years
Umm, my worst date was actually a double date. I close friend of mine was dating this guy she really liked and asked me to go with her, her date, and a friend of her date. Jesus Christ. My friend and her boy were having a great conversation, great chemistry and I was stuck with this boy, who wasn´t bad looking, but we had nothing in common. And the worst part is that he kept looking at the tv screen because there was an Australian Open tennis match going on. Idiot.
Pistil Pistil 6 years
I guess it would be the guy I met online. I should have known better. We met at his place and one of the first thing he brings up is this tantric sex/karma sutra something or other crap that he's practicing or whatever. Then he kept trying to kiss me. Um, hello? We just introduced ourselves, idiot. But I was real polite about it. Though I should of told him to f*ck off and left right then, we went to dinner anyway. I was uncomfortable the whole time and totally disgusted. I mean, I just don't get how he didn't understand how inappropriate he was being. He tried contacting me after that night, but I had him blocked on every device.
cfp cfp 6 years
I guess I should probably add that in the aftermath of that last date, all of my friends are referring to me as "the cougar" or "coug" for short.
cfp cfp 6 years
I think I have too many bad date stories to pick just one. A couple of recent ones: I went on a first date with a guy who wanted to go see a movie. I thought this was weird because my idea is that men who want to see a movie when they meet you don't have any interest in talking to you. I was wrong. Apparently, some men who choose movies may not have the ability to talk to you. It turns out that the guy didn't speak English (and my Romanian is a little rusty, believe it or not)! So basically we spent the entire time in complete silence, including the hour before the movie started that we were together. So awkward. Needless to say, I didn't go out with him again. -------------------------------------- Then just last week a guy I had been seeing was going to take me out. He tells me he's going to pick me up which he does (on his SCOOTER). So I have to ride on the back of his scooter. He then takes me to a park and whips out a frisbee. So I'm reluctantly playing frisbee, dreading the ride back on the scooter, when he tells me that he needs to confess something to me. He lied about his age. He is not 22 like he said he was. He's only 19.
cfp cfp 6 years
I think I have too many bad date stories to pick just one. A couple of recent ones:I went on a first date with a guy who wanted to go see a movie. I thought this was weird because my idea is that men who want to see a movie when they meet you don't have any interest in talking to you. I was wrong. Apparently, some men who choose movies may not have the ability to talk to you. It turns out that the guy didn't speak English (and my Romanian is a little rusty, believe it or not)! So basically we spent the entire time in complete silence, including the hour before the movie started that we were together. So awkward. Needless to say, I didn't go out with him again.--------------------------------------Then just last week a guy I had been seeing was going to take me out. He tells me he's going to pick me up which he does (on his SCOOTER). So I have to ride on the back of his scooter. He then takes me to a park and whips out a frisbee. So I'm reluctantly playing frisbee, dreading the ride back on the scooter, when he tells me that he needs to confess something to me. He lied about his age. He is not 22 like he said he was. He's only 19.
cotedazur cotedazur 6 years
When I was in college, my sorority set up a date function where you and a blind date wore matching hats, and you identified your date by finding the person with the same hat. So I'm sitting at the bar wearing a santa hat, waiting and waiting, and finally my date shows up 30 mins late. He introduces himself, orders one beer (comment to me: "sorry, I've only got enough money for my own drinks tonight"), then promptly spills it all over the bar... including all over the santa hat I'd just placed on the counter. He then gets into an argument with the bartender trying to unsuccessfully get another beer for free. When this fails, he turns to me and says, "This place sucks. I'm going to go back to my dorm and play beer pong. Wanna come?" I couldn't leave - it was my own sorority's event - so the guy says, "Ok, have a fun night!" and leaves after a total of 15 minutes, max. He also decided to put the beer-soaked santa hat back on my head before leaving. I'm left with beer in my hair, no drink, and no date.
Xemena Xemena 6 years
i had a date with a guy last year he arrived 45 mins late, and after we got to talking , two good looking girls passed our table he kept staring at them and finally said that he dosnt understand women who tell him not to look at other women because he is just looking not doing any thing more and then said that he wishes im not like those women who tell him not to stare. and there was another date also i think i was 19 then , the guy came with two of his friends they all ordered and after the introduction and hellos they said they had left something in the car which they had to go get.needless to say they never came back ,i paid the table for 4and when i got home i called up the guy to ask what the hell had happened and he said his friends didnt think i was kool so they left.
Xemena Xemena 6 years
i had a date with a guy last year he arrived 45 mins late, and after we got to talking , two good looking girls passed our table he kept staring at them and finally said that he dosnt understand women who tell him not to look at other women because he is just looking not doing any thing more and then said that he wishes im not like those women who tell him not to stare.and there was another date also i think i was 19 then , the guy came with two of his friends they all ordered and after the introduction and hellos they said they had left something in the car which they had to go get.needless to say they never came back ,i paid the table for 4and when i got home i called up the guy to ask what the hell had happened and he said his friends didnt think i was kool so they left.
gigly_grl gigly_grl 6 years
hmm I'm going to have to go with a non-date... would have to be this guy I met at a mutual friend's party on a Saturday night, when he asked me out then I figured we'd meet sometime that week but he INSISTED we meet up the following day (Sunday). He named his favourite cafe, and gave me directions but refused to give me his phone number in case something came up or I got lost (something about not giving me a "way out"). Anyway I go to the address I was given the next day, nothing there. After waiting at the exact spot for a bit, I wandered the neighbourhood for about half hour seeing if he was just off but no... so I headed home. I figured I'd get his contact from our mutual friend later and see what had happened. By the time I got home there was the nastiest and rudest message on my voicemail from the guy, completely tearing me apart for "standing him up". (He'd woken up our mutual friend to get my phone number.)I think I'm a fairly decent person and mistakes happen, people have bad days, so I got in contact with him to sort out the situation. But instead of an apology for giving the wrong directions, or even understanding that this was a misunderstanding I got a lecture and was blamed for the entire situation! I couldn't get a word in... and not just cause my jaw had dropped :P
gigly_grl gigly_grl 6 years
hmm I'm going to have to go with a non-date... would have to be this guy I met at a mutual friend's party on a Saturday night, when he asked me out then I figured we'd meet sometime that week but he INSISTED we meet up the following day (Sunday). He named his favourite cafe, and gave me directions but refused to give me his phone number in case something came up or I got lost (something about not giving me a "way out"). Anyway I go to the address I was given the next day, nothing there. After waiting at the exact spot for a bit, I wandered the neighbourhood for about half hour seeing if he was just off but no... so I headed home. I figured I'd get his contact from our mutual friend later and see what had happened. By the time I got home there was the nastiest and rudest message on my voicemail from the guy, completely tearing me apart for "standing him up". (He'd woken up our mutual friend to get my phone number.) I think I'm a fairly decent person and mistakes happen, people have bad days, so I got in contact with him to sort out the situation. But instead of an apology for giving the wrong directions, or even understanding that this was a misunderstanding I got a lecture and was blamed for the entire situation! I couldn't get a word in... and not just cause my jaw had dropped :P
totygoliguez totygoliguez 6 years
Chouette4u and anonymous 4:52 those are horrible experiences! anonymous thank God that the guy did not do something to you. If that ever happens to me I wouldn't care to be polite I would run out of the place and call him a lier.
jpk587 jpk587 6 years
This guy picked me up to take me on a date. First of all, he takes me to Subway...on his motorcycle. He then proceeded to talk the ENTIRE TIME about himself. I didn't say one word. Then when he dropped me back off, he took off his helmet and handed it to me. I accidentally dropped it, and he got really angry with me for getting a scratch on it. Yeah, douche bag.
mix-tape mix-tape 6 years
I went on a date with a guy and it was alright, I invited him back to my place, but he didn't make a move on me and ended up staying over at my apartment until 5 am! No kissing, no cuddling, definitely no sex involved. We talked about everything, including his grandma who has Parkinson's... which then caused him to cry. This was a FIRST DATE!! Needless to say, we never went out again. (wow I seem heartless reading that back to myself)
fuzzles fuzzles 6 years
While in college, I went on a rollerblading date with a friend of a friend. We had gone back to his basement apartment after to chat and have a cold beer. While sitting on the sofa, something started flapping, mid-air, in the living room. It was a forking bat! One of the last images I had was of the guy chasing the thing with a tennis racket. I screamed, both literally and figuratively, into the nearest bedroom. I also fled through a window. Without my shoes.
Latest Love
X