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Cringe-Worthy Dates That Will Make You Want To Cry

People have gone on some pretty bad dates. The conversation could go south, the food could taste horribly, or there could be no chemistry. No matter what turns the date sour, you often end up with a pretty good story or even two. Recently, someone was interested in these stories. They asked the question, “What’s the worst date you’ve ever been on?” It may be hard to choose just one horrible date story! 

Restaurant Issues

Woman looking surprised with arms out to the side in question
Image credit: Depositphotos AllaSerebrina.

One person wrote, “A guy who found me on Facebook asked me out. He asked where I wanted to go, and I asked, “Do you have anything against sushi?” he said no, so we met at a sushi place. I ordered sushi, and he ordered something else, and when my food came out, he goes, “Blech! I hate raw fish!”

Another person added, “Went on a date once with a girl who ordered enough food at the restaurant. I took her to load up a nice-size take-home box, then got some nice drinks on my dime at the bar. About midnight she informs me that she needs me to get her home because she’s got a date with the guy she’s sleeping with that night.”

Toxic Personality

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A Redditor commented, “I went out with a girl who spent most of the date telling me how much she hated her sales manager at one job and how she could totally get the girl fired because she’s in good with the big manager. Then she told me she got suspended from her serving job for saying rude **** to a co-worker. “

Parent Issues

Woman crying into her hands
Image credit: Depositphotos AndrewLozovyi.

A popular comment said, “That would be the time that my date and I went to a movie, and while we’re leaving the movie to head to a coffee shop in my car, she looks out the window and sees her father leaving the same movie with a woman who isn’t her mother… while her parents were still married. They ended up getting a divorce.”

Another user added, “So during high school, my mom wasn’t a huge fan of me being bi, so my girlfriend was a secret. Unfortunately, my girlfriend fits a few (all) of the “dyke” stereotypes… Short/dyed hair, a big flannel fan, etc., so my mom was pretty suspicious of us being just friends. I was going to borrow the car to take her on a movie date when my mom declared she was coming too.”

Religion Issues

Husband and Wife back to back looking at one another with angry looks
Image credit: Depositphotos Vadymvdrobot.

A very awkward date was, “Met my date at a wine bar thinking we were going to have a regular person date. Things were going regular until he pulled out his bible and started reading me all the parts where a woman’s place is in the kitchen serving men.”

Another user added. “I went on a date through Tinder once, and the girl ordered herself an expensive entree and appetizer, plus a few beers. When the bill came, it was around $100 for both of us. I paid because I hadn’t been on a date in a while, and she was nice. But she then told me she wouldn’t go out with me again because I’m an Atheist, and she can’t be seen dating one of those.”

Another Man

three people sitting on a bench showing two are cheating and holding hands
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One Redditor replied, “Took a girl out to a bar for food and drinks. It was going ok, then her friends showed up, along with some other guy she knew. She started talking to him a lot, sometimes disappearing to go talk to him somewhere. Then she started openly flirting and dancing with him in front of me.“

Another cringy story said, “Apparently, she wanted to invite her ex to the whole thing. Good thing I didn’t know that until she showed up. Then after she and her ex started getting closer to each other, he professed his love for her in front of everybody and PROPOSED. Of course, she said yes, so he carried her out and left me with the bill for the two steaks the guy had.”

Pick Up Lines

Pyschoanalyzing on the First Date: woman looking upset and holding hands on head while sitting in a chair.
Image credit: Depositphotos eldarnurkovic.

A comical story was, “Not me, but a friend of mine. He took this girl out to The Cheesecake Factory as an eighth grader. They sat down, and when the waiter came over, he just asked for water, nothing else, and wouldn’t let his date order anything. She was pissed and confused, to say the least. So the waiter brought their water, and my friend sent him on his way. My friend takes the water, dumps it on his date, and says, “I just watered a beautiful flower.” The girl walked out right there.”

Stood Up

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One sad story was, “I drove an hour out of my way to the place we were meeting. She sent me a picture of where she was sitting so I could find her easier. When I got there, she was gone. She didn’t answer my texts, and I never heard from her again. That was the first and only time I’ve (almost) been on a date, so it was really upsetting to me.”

Cheap Date

Woman throwing a napkin at her date at the table
Image credit: Depositphotos VitalikRadko.

A Redditor replied, “He paid for our Orange Julius with a buy one get one free coupon. Brought a refill cup to the movie and alternated between staring at me and biting his nails. Afterward told me he didn’t have a car, so asked for a ride home. He left the refill cup in my car and texted me every day asking for it back. Threw cup away.”

Aliens Exist

So Like… man on the phone
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One weird first date was, “He spent the entire time (like 3 hours) babbling about aliens and the government conspiracy to cover up their existence. Among tons of other crazy ***, he said he could contact them psychically through group meditation. then he showed me youtube videos about it. I’m still not sure whether it was a date or an attempt to recruit me into a cult.”

Already Taken

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Image credit: Depositphotos – AndrewLozovyi

One Redditor wrote, “A few weeks ago, I went on a date; the date itself was pretty good, so I was telling my good friend about it and how I really liked the guy. It turns out my date had just celebrated his 1-year anniversary with my friend’s friend….”

Another Redditor added, “I was just talking with a new friend at university, and she was telling me about her roommate. Turns out I had actually chatted with him online a bit when I first moved here a year ago. I mentioned that. Coincidentally, I had just seen him tagged in a picture on Facebook with a guy I had gone on a date with the week before. Turns out they’ve been dating since January. I know that feeling.”

Unsure of Sexual Orientation

Woman wearing a green dress looking confused
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A user replied, “ She had like a 5mm shaved head and a smexy punk look going on. We had SO MUCH in common. We literally talked for hours about Buffy, the vampire slayer, and it was great. Well, turns out she was a lesbian, and my friend had misunderstood her as bi. And for whatever reason, she didn’t think it was a date when a dude she met once at a party called and asked her out for coffee.”

Phone Habits

One-Sided man and woman sitting at a lunch table man on his phone woman looking at him upset.
Image credits: Depositphotos YAYImages.

One Redditor commented. “Girl came in the theater talking on the phone, didn’t hang up till the trailers, and then proceeded to text 3 people simultaneously, calling one of them baby. At this point, I was ready to walk out on her. I don’t know why I didn’t, and then as soon as the movie ended, she called and talked to someone the whole time while I was driving her home. It was so damn disrespectful and rude.”

Swipe Right

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A comical story was, “She went on a date with someone she met on Tinder, and there was 0 chemistry. After the awkward date, he gets up to leave, snaps his fingers at her and points to her, and goes, “Thanks for swiping right ;)” and leaves.”

Buy One Get One

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Image credit: Depositphotos kues.

A user replied, “Not me but a friend. A guy she worked with in the office asked her out for dinner. He suggested a restaurant. They ordered and ate their dinners, and when the bill came, he put down his half, which happened to be a buy one entree-get one free coupon. He paid for his Pepsi and let her take care of the rest of the bill. Okay, I guess that’s not so terrible, but I thought it was pretty funny. He must have been sitting at work thinking, “How can I get the free meal from this coupon.”

Jail Time

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One Redditor responded, “Met a girl on Tinder, and we decided to go to brunch. She was really weird about not drinking a single drop if she was driving. But if I drove, she’d love to get bottomless mimosas. Figuring that might get me laid, I didn’t notice the red flag. About 15 minutes after we sat down, she proceeds to tell me how she just got out of prison for manslaughter involving a DUI. That kind of killed the mood.”

A second Redditor added, “We met online. He seemed like a nice guy. Good job, great conversation, and lots in common. Then, just as dessert arrives, he breaks out the old ‘so, I should probably tell you something. I’ve been to prison. For murder.’.”
Redditors sure have had some pretty bad dates. What is your worst date story?

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