11 Hilariously Bad First Dates That Triggered a Welcome Dating Hiatus

Author image for Jesse Kessenheimer
Jesse Kessenheimer • Writer and Editor
Mar 12, 2026 12:00 PM EDT

Bad dates live rent-free in our cringe catalog for life, but some, more terrible first dates go down in relationship history… In the most hilarious way. 

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  • What's the worst first date you've ever had?
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  • I got married young (when I was 22, actually), and I don't think there's a day that goes by that I'm not thankful to be free of the dating world. 

    Lucky enough to meet the love of my life pretty early, I witnessed my friends, buddies, and besties go through some of the strangest relationship encounters out there. As the “designated married friend," I was the perfect sounding board for all of my homies in their early 20s, who met drummers after shows, dated aspiring artists, and went on blind dates with unemployed MLM schemers. 

    Through their experiences, I can proudly say that I'll never set foot in the dating world no matter what happens. Because when you mingle singles who are desperate for romantic connections with the social awkwardness of meeting for the first time, you're bound to create the perfect storm of hilarious dating tales that'll resonate in the friend group for all time. 

  • Afraid Square3488 She asked to meet at a local park instead of the coffee shop we originally agreed on. Cute, right? I show up,
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  • and she's there with a 5-year-old kid. She says, 'Oh, I'm actually nannying right now, but my boss is paying me $25 an hour, so I figured I'd multitask.'
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  • Ten minutes in, she asks me to watch him so she can 'take a quick phone call in her car.' She drove to the gas station and left me alone with a stranger's
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  • child for 40 minutes. I basically got tricked into doing free freelance childcare.
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  • 2
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  • Luring their date into handling their nanny job, this woman has either cracked the code on free labor or is genuinely insane. There's a lot you can tell about a person in the first few moments of meeting them, and when they throw their employment responsibilities upon you in the first few moments after a handshake, you're looking at the most entitled of sorts. 

  • Content-Strength-275 She said my dog was not cute. And followed that up by saying that Jaws 2 was better than the first.
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  • If you straight-up call someone's dog ugly, it's over. 

    Perhaps as a joke, or if they have a snaggle-toothed pug that snorts in its sleep, it might seem funny or laughable to insult their appearance. But if a date genuinely hates on another person's pet, I think that's an enormous red flag that cannot be ignored. 

  • Evening Reception We matched on a dating app and set up a date at a bar around where she lived. I show up and her brother is there with his wife. I thought
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  • it was pretty odd, but maybe they were there for her safety and would leave eventually. Nope, we bar-hopped to 3 different bars and they were there the entire time at each
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  • place. Later in the night she told me her 18 year old son convinced her to get on the dating app because he thought she should put herself out there. Oh and she
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  • also mentioned the Dad had 7 DWI's. When I left to go home I went over to her brother to say goodbye and he was like "there's plenty of other women here if you want to stick around." Worst first date ever.
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  • Divine-Magician-9295 I was 16 and I met a guy who wanted to sit by the lake ((I used to live near a beautiful lake and it had a boat
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  • dock so there was a bunch of lights and it was just so peaceful to look at during sundown and at night)) and so we were hanging out and talking and
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  • randomly he pulls out an old electric toothbrush that he made into a tattoo g n and he starts tattooing himself. I'm staring at
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  • him very confused cause I've never seen anyone do a tattoo not in a tattoo shop ((my mom worked in a tattoo shop and this is where I met this guy.
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  • He came in while his mom was getting a tattoo)) but he had ink and everything. I asked. him what he was doing and if he thought that
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  • was clean/ a good idea and he said was like "it doesn't hurt. Everything is cool" and then he grabs my hand and places a dot right on top. I was screaming
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  • and fr king out and made him take me home. I still have that dot on my hand and my mom took me to get every std test under the sun the next
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  • day cause that kid stabbed me with his used needle.
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  • I have a couple of tattoos, but never in all my years would I consider getting one on a first date from a stranger who made their own tattoo machine with an electric toothbrush. Sorry, buddy, but there are some lines that should never be crossed, lest you risk a quick trip to the emergency room for a tetanus shot.

  • U -
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  • TrinixDMorrison Her phone kept going off during dinner and while she didn't respond to it she did keep checking her phone. I was a little
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  • annoyed and told her she can go ahead and respond since it sounded like an emergency. She then told me it's not an emergency and that
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  • it's "just her boyfriend". This took me by surprise since I thought she was single, and when I told her I don't want to get
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  • caught up in whatever drama she's got going on she told me that she's been meaning to break up with him for a
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  • while now so she's practically single, it's just that he doesn't know it yet. So yea, noped right out of that red flag.
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  • Responsible-Rub2732 High school. Came over to her house one weekend just to hang out, watch a movie.
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  • Walk in and her mom says "ohhh finally, this must be lan." My name is not lan
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  • gin10do64 I was 21 and I met this guy at a restaurant. When I get there he is already sitting down at a booth. We start
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  • chatting and I ask him what he does for work. He tells me that it's easier to show me what he does for work and
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  • proceeds to pull out a backpack and start setting up a laptop. He starts showing me a slideshow presentation for an MLM called juice
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  • plus. He tried to tell me juice plus cured his mom's diabetes. I told him how ridiculous that claim was. We got
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  • into an argument about MLM's being pyramid schemes. At least I never ended up in an MLM.
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    via Jaden Becker
  • Active-Strawberry-37 We met online and agreed to meet in a local pub. When I arrived, she took me up
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  • to the function room and I got to meet her entire extended family at her granny's 80th birthday party.
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  • ISWG He told me he was married halfway through. When I was shocked, he said it was just a visa situation to help her come over
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  • from his home country. As I questioned further, it turns out that she was in love with him, both families had attended
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  • and supported the wedding but he just thought she was too homely and wanted to explore his options before she permenantly landed.
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  • silverpotato5955 Not single any more, but i met someone for coffee and within ten minutes she started interviewing me like a
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  • recruiter about salary, credit score, health issues, and five year plan, then told me i should probably switch careers because my
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  • current one doesn't scale well, which was impressive considering she still didn't know my last name. I don't get the job but that's probably for the best
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