The Ultimate List of the Worst Dates Ever


Worst date ever

(Last Updated on July 24, 2019 by Datezie Editors)

If there’s anything we can all agree on, it’s this: dating sucks. Even if you’re been happily coupled up for a while now, you still shiver at the memory of all the terrible experiences you had to endure to meet your one-and-only. Or, if you’re currently in the trenches (godspeed!), you probably get anxious stepping into another first date, unsure of what’s waiting for you at happy hour drinks. While we’re sorry for everyone — including ourselves — who have to suffer through the bad stuff to find the good, we can’t help but laugh at the horror tales. Scarier than snakes on a plane, spiders in your car and the entire concept of ‘Naked and Afraid’ — these dates-gone-wrong will have you LOLing. Do you have one to share yourself? We’d love to add it! Email us here

The lead-her-on.

“It was my junior prom and one of the guys I liked wanted a date to the Prom. At dinner, he asked if I wanted him to pick up my meal. Embarrassed I said ‘Absolutely not, I got it.’ Later, at the prom, he danced with five other girls and only one song with me. I realized at that point that he used me to get into the prom to be with other girls as he had already graduated. It ended up being okay because we are still friends, but I decided to attend senior prom alone and had a blast.” —Emily, North Carolina

The gold digger.

“We met on Bumble, and he seemed well to do and put together. But, he showed up in cargo shorts. Then, asked how much money I made five minutes into the date. Then he complained about money half the time, followed by Donald Trump fanboy-ing. He asked me to split it, so I covered it all. Worst. Date. Ever.” —Danielle, Florida

Too far, too fast.

“I met this guy at a church event. He took me out for my birthday about three years ago at a fancy Italian restaurant. He ordered something that looked really delicious to me but he complained about it to the waiter. The waiter had it re-cooked and brought it back out looking even better — and my date complained again. He told the waiter that he did not want to eat any of their food. So I ended up eating by myself while he just sat there. To start, that was embarrassing. Then he took me on a walk by the river and he kissed me and very quickly started to try to turn it into a make out session. While usually when a guy bites your lip a little bit it is sexy… but not this time. He bit my lip multiple times so hard that it started bleeding! After that date he never texted me again. I was considering giving him another chance but in hindsight, I am so glad that we never spoke again.  —Julie, California

Stage-five clinger.

“I don’t go out to nightclubs very often but I decided to go out with a group of my girlfriends and just have some fun. While we were there a guy asked me to dance and I agreed. I found out that he was from a city about an hour and a half away. He asked me if he drove back into town the next weekend if I would go on a date with him. I agreed. Fast forward a week and we ended up going to a popular dessert spot downtown and talked. The entire time he only talked about himself and he bragged about the bodybuilding that he used to be into and showed me pictures of himself posing at the competitions that he went to. That was annoying — but then it got really weird… He started talking about marriage and asking me if I would consider marrying him if things worked out. Then he started asking if I would move to his city if things moved quickly. Maybe some girls are cool with that, but I am not one to agree to marriage or moving on the first date, especially when I was in college and working toward my dream career. 

So for about two weeks after the date we texted a little bit but I ended up not really feeling a connection with him and we didn’t text for a while. One day he texted me again and I told him that my feelings were not the same as his and he went off on me about how I led him on and said some really hurtful things.

A year later I found out that one of my friends knew a girl who went on a date with him as well and he started talking marriage on the first date, too. When she did not reciprocate his feelings he also got mad at her and said the same mean things. It’s been a few years since then so hopefully he has learned how to talk to women respectfully by now!  —Jordan, Utah

The Catfish.

“We met on Bumble and he’d been uber eloquent on messages but meeting in person was a little different! He was late, rather agitated and I spotted within minutes he was on the spectrum. He started the date by telling me his last three dates walked out on him. When I asked him why, his misogynistic, pro-Brexit and racist comments made it obvious. I tried to politely educate him before I left but his lack of awareness of personal space was the too annoying. What a waste of an evening!” —Lily, London

Unexpected S&M.

“We met on a singles holiday and he was a cute, intelligent guy, maybe a little quiet. We met up again after the trip and that’s where I remembered he was too beta for me: he couldn’t make decisions, couldn’t order the wine, just too tentative. Then he starts working S&M into the conversation and it turns out he’s secretly a dom, looking for a sub. It’s a this point, I try to keep a straight face as he’s clearly the worst dom ever and I’d make the worst sub ever! Then it turned into a counselling session where I listened to the turmoil of him leading a double life. We did not meet again!” —Nicole, Paris

A non meet-cute.

“I planned a first date with someone from OkCupid. We met at Kramerbooks, which was like a dream meet-cute destination for me at the time. When I was in the bookstore, I was looking around at the books waiting on the guy I had such great chemistry with online. I was wondering if I had been stood up when I was approached by a man who had also been circling the store, but looked nothing like the guy I had been charmed by via messenger. He walked up to me and said ‘You’re Michelle, right?’. My heart sank. Not only was I not attracted to him, but my guard went up that this guy was using pictures that looked nothing like him. 

We went to the cafe in the back of the bookstore for a really expensive dinner. I got like three words out the whole time because he wouldn’t stop talking about how all his friends were girls, and they all thought he was such a catch and didn’t know why he was single. It was so painful and I insisted we split the check so that he would know this wasn’t going anywhere. That didn’t work though: he emailed me immediately telling me he thought we were destined to be. I blocked him on all avenues of communication and my mom reimbursed me for the bad date out of sympathy.” —Kate, Washington, DC

The dine-and-dash.

“At the end of a bad blind date I reached for my purse to pay my half. My date, chivalrously, told me to put it away and asked me to grab the check while he went to the bathroom as was happy to pay it. He never came back. I paid the whole thing.” —Loren, New York

The meat lover — and meat head.

“We met on and he seemed very down to Earth. We met for coffee two times and then planned a dinner. I had mentioned I was vegetarian and he said he had a great place to take me. We went to a nice looking restaurant, and to my surprise, there wasn’t much I could eat — except for the side dishes — as he took me to a purely seafood restaurant. The waitress came to get the drink orders and he took the liberty to order for me, and I politely said I wasn’t drinking because I had taken a prescription medication before hand. His response? ‘One drink never killed someone with a pill.’ The look on the waitress’s face was priceless. 

Then she asked if we wanted any starters; he said no and went to order — for the both of us. I cut him off saying, ‘Hey maybe you forgot, but I’m a vegetarian.’ He looked at the server and said, ‘Bring two side dishes for her which are vegetarian and you serve fresh rolls here, right? I think I remember from the last time you did. Bring her some of those too.’ So he expected me to eat a side dish and the free rolls which they serve. I excused myself to go to the bathroom. Maybe a few minutes later he text me asking if I had ‘fallen in the toilet,’ and I responded with, ‘No, I almost fell for a male-pig, and BTW, on my way to Tao to have a vegetarian dinner with my friends.’ No response after that, ha!” —Michelle, New Jersey

The squatter.

“We met on Hinge app, where he said he graduated from MIT. When I asked about this, it turns out he didn’t go there for schooling, he just had lived there. But get this: in the Student center, under a desk for three months until security found out and he was escorted off of campus. Needless to say, that was our first and last date.” —Danielle, Boston

SOS: Need an escape plan.

“We met on OK Cupid, and decided after a few days of texting to meet up for a date: ice skating and a quick bite. He arrived 45 minutes late because he couldn’t find the parking garage, an error he blamed me for because I gave ‘bad directions.’ Upon greeting him, he told me the ice rink was too cold — and that we should just go eat. Fine. After some debate, we finally settled on Noodles and Company as the place to dine. About fifteen feet from the door, he full-sprinted to the restaurant and ran inside. I didn’t understand why until I caught up: he was very quickly ordering so that he wouldn’t have to pay for me. Whatever. So I ordered a kids portion of mac ‘n cheese and sat down to try to talk to this guy. 

Sad part was, any question I asked him he would answer in ten words or less, then stare at me with his mouth open. Our food came quickly and he looked at my half cup of macaroni and side of tomato soup and said ‘You know, if you keep eating like that you’re gonna get fat.’ He then stared at me with his mouth open waiting for a response, when a glob of drool rolled out of his mouth and onto his shirt without him noticing, which lived there for the rest of the date. 

After more awkward conversation, we wandered out of the restaurant and he eyed a Cold Stone that he had to have. He ordered a ‘Gotta have it’ size and he ate it in silence as I pondered how fat he’d call me had I ordered a half gallon of ice cream. 

I finally told him I was sick and needed to go home, and he walked me towards my car when we passed a Simpsons arcade game. He freaked out with excitement, told me he hadn’t seen one in 36 weeks and pulled a roll of quarters out of his pocket to play. He did not offer for me to play. 

And every time I mentioned that I really, really wasn’t feeling well he’d tell me he was wrapping up. Finally, after much grumbling, he finally stopped playing and walked me outside. At my car I told him thanks for taking me out and in one swift movement he leaned it to kiss me! I went full Matrix, 90-degrees straight back and told him I felt contagious. Later, I got a gushing text about what a wonderful time he’d had and how much he’d like to see me again. I told him I was really busy with work and that I was unavailable again for a few months. Wouldn’t you know it, a few months later he contacted me to see about ‘taking me out’ again. Let’s just say the answer was ‘no.’”—Anne, Florida

Was it a date — or a game show?

“When met on Tinder and decided to go to a local bar. He not only arrived twenty minutes later, but then he spend 30 minutes showing me photos on his phone of infected dog uteri. To be (borderline) fair, he’s a vet tech, but is that really an excuse? No. All I had said previously was that I loved animals and had worked in the pet division of my PR agency, so I worked with animals often. Not only did he show them to me, he began to ‘quiz’ me on the different uteri. One uterus was pregnant, one was infected. You get the idea.

He also quizzed me on pretty much everything the entire night. On how to play darts, on the music we played on the bar’s ‘jukebox.’ Needless to say, I wasn’t feeling well that week anyway, so I told him I had to cut the night short and wanted to go home. Then an unexpected conversation came up:

Him: ‘Let’s go home and watch TV at your place.’

Me: ‘Um, no. I’m going to go home by myself. Plus, I don’t feel well.’

Him: ‘No, you get the wrong idea! I didn’t want to do anything. I just want to lay next to you.’

Creep. City. I awkwardly let him kiss me at the end of the night, but only to get rid of him. Although he told me at one point ‘I’m getting in your car with you.’ and I said ‘No.’ Thankfully, he left it at that. My roommates later told me I’m lucky I didn’t end up in the trunk of his car. We joke now, but I think back and feel lucky that the night ended the way it did.

I don’t think I need to say it, but I ignored his follow up texts for a second date! I don’t like to ghost, but I think this was warranted. Thankfully I met my current boyfriend on a Bumble and we have been together more than two years!” —Fiona, Virgina

He had a dog. But also l lived with his mom.

“Following the end of a three year relationship, I had no idea how to get back into the dating scene. My brother, who was also recently single, and I agreed to make Tinder accounts together just for the heck of it. It quickly turned into an intense game of swiping left, right and sending screenshots of horrific messages to each other. 

One day I received an insanely funny message about my bio — something about always asking to pet strangers’ dogs — and we hit it off. I agreed to meet this mysterious Tinder man, who indeed had a puppy, for a sushi date while my brother secretly met a Tinder contestant at the same restaurant. 

I get there and the guy was. so. awkward. 

I took it upon myself to start drinking vodka sodas to get myself through while my brother and his date laughed in the background. Afterwards, I was so excited to leave when he said, ‘We should back to my place… I just have to sneak you in through the back door so that my mom doesn’t see.’ 

This was after he told me he had his own apartment, which ended up being his mom’s basement. I flat out said ‘no’ and that it was time for me to call it a night. Needless to say I deleted my Tinder account and haven’t used it since! The guy did message me on SnapChat a few times afterwards but I think he eventually got the message. My brother on the other hand met his dream girl and they’ve been together for almost two years now! “ —Isabella, New York

Wait, what?

“I was living in LA and met this guy through a college friend who played on the same league soccer team. He thought he was David Beckham — haircut and all — but he was nothing further. We met for drinks and sat at the bar for our first date. When the bartender poured my wine, fake David Beckham turned to me and said, “Now what do you say when someone pours you a drink? You say thank you.’  As if I were a child. 

That left me on a sour note but we ended up hanging out the rest of the night, but I had to split the bill with him when the tab came. I ended up going out with him two more times — LA makes people do stupid things, I guess? He was coming to my house to watch a movie and asked if I had any snacks, otherwise he was going to eat before he came over. Some time during the night he told me I was the 101st girl he’s gone out with in LA. Wow!

Then the final straw was when I went out for drinks with male friends and we took a group picture. As soon as it went up on Facebook, he started blowing up my phone: accusing me of hooking up with the guy closest to me in the photo! Whereas that guy he was so jealous of happened to be in the closet and didn’t come out to the rest of his team yet! Needless to say, I ignored him.” —Larina, Los Angeles


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