Getty Images via Kevin Mazur

Check Please: 29+ Hilarious First Date Disasters That Sent People Running for the Hills


| LAST UPDATE 10/17/2021

By Kayla Black

It's no doubt that first dates can be rather uncomfortable, from awkward conversations to run-ins with ex-girlfriends. Check out these tweets about people's hilariously tragic first dates.

Flirting Failure

Well, this sounds like an unfortunately uncomfortable way of flirting. Imagine being on a first date, and the person not only stares at your zit but also points it out by assuming you dropped food on yourself.

Flirting Failure First Date DisastersFlirting Failure First Date Disasters
Getty Images via Kevin Mazur / Twitter via @stuart_edge

This man said it looked like ice cream on his date's chin, which seems weird, considering they probably hadn't even ordered dessert yet. Well, let's just hope these guys can laugh about it later, right?

'Lady and the Tramp' Style

Raise your hand if you've ever pictured a romantic date where you and your significant other share a plate of spaghetti and eat it just like the characters from Lady and the Tramp. The concept seems quite romantic, but to avoid an awkward outcome, it might be best to wait until you've been on a few dates with someone to do this.

Lady and the Tramp Style First Date DisastersLady and the Tramp Style First Date Disasters
Instagram via @selenagomez / Twitter via @mc_arthur123

In this case, the girl happens to be a hopeless romantic and had big aspirations for her first date. Therefore, she went for the Lady and the Tramp style of eating and temporarily forgot about her pepper sensitivity. Once she got a whiff of that extra strong pepper, it was game over, and the romantic idea became a saucy mess.

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Unwanted Trip Down Memory Lane

Don't you just love it when you find yourself on a date with someone who only talks about themself? Even if you try and tell this individual more about yourself to get to know you better, they always bring the conversation back to them. Who has time for dates like this these days anyway?

Unwanted Trip Down Memory Lane First Date DisastersUnwanted Trip Down Memory Lane First Date Disasters
Getty Images via Noel Vasquez / Twitter via @Vegan_chick_MI

But, you know what could make this type of date even worse? Having to hear about your date's ex-girlfriends. And not just one or two, but literally every girl he's ever dated. If that's not enough, he'll happily show you each of their houses, so you can see all the doors he walked these girls to.

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When Social Media Backfires

Have you ever stalked someone on social media right in front of their face while hoping they never glanced at your screen and found out? Well, that's precisely what happened here, except the girl on the date wasn't very sneaky while complaining about the guy on Facebook.

When Social Media Backfires First Date DisastersWhen Social Media Backfires First Date Disasters
Getty Images via Scott Barbour / Twitter via @kingedhill

In a very public post, she accidentally wrote her date's name, which caused her to tag him, and before she knew it, essentially, the whole cyber world, including him, was aware of this seemingly lousy date. Poor guy, how does one recover from a discovery like that? Do you think he ended the date right then and there?

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Too Soon for Baby Names

Plenty of people try and imagine a future with someone they're dating, to see if it seems realistic and desirable, of course. However, telling your date about these future plans or ideas doesn't always go over very well, especially when you've only known each other for less than an hour.

Too Soon for Baby Names First Date DisastersToo Soon for Baby Names First Date Disasters
Getty Images via Getty Images/Handout / Twitter via @SophisticateKay

Five minutes into their first date, this guy already started brainstorming names for the potential couple's children together. Let's be real here, he might not even be into her, but it hasn't been long enough to find that out. How would you react to your date talking about a future together after just a few minutes?

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It's Called Research, Not Stalking

There's nothing wrong with doing some pre-date research on the person you're about to meet for the first time. However, you must never reveal any personal information you've discovered, unless it comes up in conversation, of course. Especially things that the person probably wouldn't bring up.

It's Called Research, Not Stalking First Date DisastersIt's Called Research, Not Stalking First Date Disasters
Getty Images via John Shearer / Twitter via @micromush

For instance, if the guy you're meeting starts talking about his aunt, it might not be the best idea to immediately ask which one, even if you've memorized his entire family tree. It's great that you have a basis of knowledge on this complete stranger, but let him share what he wants to share, and go from there.

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Karaoke Took an Awkward Turn

If you're looking for a fun first date idea without the awkward small talk, then karaoke can be a great activity. Except, what do you do when the girl you're dating starts singing about her ex and makes it relatively clear that she'll always love him? Yikes... that's gotta hurt.

Karaoke Took an Awkward Turn First Date DisastersKaraoke Took an Awkward Turn First Date Disasters
Getty Images via Al Pereira / Twitter via @ParkSwish3

Do you just get up and leave, or be brutally honest and confront the girl? I mean, there's no harm in asking why she even went out with you if she clearly still wants her ex, right? Either way, at least you got some quality entertainment out of the night, so that counts for something.

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Don't Be Scared

When a stranger tells you not to be scared on a date, there are probably many thoughts that go through your head. Could this mean you're sitting with a serial killer? Well, if that's the case, then be scared! But, what if your date is perfectly safe and just has a little party trick that some people find alarming?

Don't Be Scared First date DisastersDon't Be Scared First date Disasters
Getty Images via Kevin Winter / Twitter via @BronwynRoberts

By alarming, we're referring to his fake tooth that sometimes has a tendency to fall out. On the one hand, at least he did the right thing and gave you a fair warning. If someone whispered this in your ear, would you still give them a shot? Let's just hope the tooth doesn't end up in the girl's mouth.

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An Unexpected Guest

Meeting your significant other's parents, or really any family members can be quite nerve-wracking. Many people wait until the relationship has gotten rather serious, so when mom starts asking intense questions, the couple can answer them together, with a better idea of where they're heading.

An Unexpected Guest First Date DisastersAn Unexpected Guest First Date Disasters
Monster-in-Law via New Line Cinema / Twitter via @JessicaBlu

What would you do if your date's mother strutted in on the first date? In this instance, this guy's mom approached the table and proudly introduced herself to her son's date. Apparently, she'd been waiting for her son in the car and needed to use the restaurant's restroom. Let's just hope she didn't scare the girl away.

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Does That Mean No?

It's no secret that many people have a hard time dating again after a devastating breakup. So, if you happen to know that your date just got out of a long-term relationship, it's probably best not to bring it up and focus on the present; Maybe even the future (but not too far into the future, of course).

Does That Mean No? First Date DisastersDoes That Mean No? First Date Disasters
Getty Images via Jim Spellman / Twitter via @jeff_hofmann

Perhaps it'll even go well, and the time will come to ask her out on a second date. Let's hope she says yes, but if she says no, well, better luck next time! But if she says she's going to take a break from dating overall, does that count as rejection? Wow, dating can be so complicated!

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At Least the Waiter Was Honest

Apparently, plenty of people have their go-to date venues, and frequently, the waiters begin to pick up on the patterns. Like in this instance, where a woman was on a date with a man she'd met online and was pleasantly surprised that she was having a lovely evening with him.

At Least the Waiter Was Honest First Date DisastersAt Least the Waiter Was Honest First Date Disasters
Getty Images via Theo Wargo / Twitter via @JessieB365

She never would've suspected anything until the waiter decided to come clean about her date. And that's how the woman discovered that she was the man's third date of the week, at the exact same table at the same restaurant, with the same waiter. Well, at least the waiter was honest, right?

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Who Said We're Splitting the Check?

In many cases, there's an assumption that one person will take care of the bill on a date, and some people even get offended when this doesn't happen. In this scenario, the guy ate a luxurious steak dinner and a few fancy beverages, while his date ordered nothing but a salad and some water.

Who Said We're Splitting the Check? First Date DisastersWho Said We're Splitting the Check? First Date Disasters
Blended via Happy Madison Productions / Twitter via @kittykaresless

And to the woman's surprise, her date demanded that they split the bill when realistically, they didn't even order equally valued meals! What would you do if you found yourself in this situation? Maybe she argued with him, or perhaps, she threw a drink at his face and stormed out of the restaurant.

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When He Still Lives With His Parents

Plenty of people live with their parents at some point in their life to save money, and some people find that to be a complete turnoff. Especially when someone has to sneak their date into their parents' home after curfew at age 30, to then reveal they use the same bedsheets from when they were 13.

When He Still Lives With His Parents First Date DisastersWhen He Still Lives With His Parents First Date Disasters
Modern Family via ABC / Twitter via @tinyelvisbkwd

Do you think this woman would be as angry about her date living with his parents if he was honest about it from the start? Well, even if she was, then at least she could've avoided the date overall, rather than making fun of this man's teenage Ninja Turtle sheets.

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Dress to Impress... Or Not

If you were told that someone was taking you on a date to one of their favorite places, do you think you'd dress to impress? Well, this girl certainly did, as she'd assumed she was embarking on a night out on the town, with a fancy dinner, a scenic view of the city, and maybe even some dancing.

Dress to Impress... Or Not First Date DisastersDress to Impress... Or Not First Date Disasters
Getty Images via Steve Granitz/ Twitter via @Jcrunkk

Clearly, this girl had no idea what her date genuinely loved to do for fun, hence why she ended up wearing a ballgown to a fishing equipment shop. You could probably say she was a bit overdressed, am I right? Luckily she now has a better idea of the dress code with this guy if she gave him a second chance, that is.

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Finding Out You're Related to Your Date

Ahh, what a small world it truly is. Especially when you're set up on a blind date; The possible connections with this person are endless, and you probably didn't even know it until you got to talking. But, what if you discover mid-date that you're a lot closer to this person than you'd ever imagined?

Finding Out You're Related to Your Date First Date DisastersFinding Out You're Related to Your Date First Date Disasters
Getty Images via Getty Images/Handout / Twitter via @ChrisKonya98

And by close, we literally mean related. There may or may not be any blood relation, but even if your date's great aunt married your fourth cousin, dating someone you're somewhat related to can get weird. But hey, if you guys remain friends, then at least you'll always have a funny story to tell, right?

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Thanks, But No Thanks

Buying a gift for someone you don't know very well can be tricky, as you might not know what would make their day and what would absolutely turn them off. You could say this lady was far from impressed when her date bought her a box of brown hair dye as a Christmas gift.

Thanks, But No Thanks First Date DisastersThanks, But No Thanks First Date Disasters
Getty Images via Jamie McCarthy / Twitter via @KristensenEmily

For starters, he might've come on a little strong buying a gift on the first date. Also, implying that this girl should change her hair color probably isn't the way to make a great first impression. Unless he wanted her to use it on his hair because he wanted to change things up. But still, that could also seem strange.

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When the Cat Comes Out to Play

When it comes to dating someone who's attached to their pet, that means learning to love the animal too. And if you don't, then you risk getting on your significant other's bad side. When this woman met her date for the first time, she was surprised to discover that he'd planned a romantic evening for the two of them with his cat.

When the Cat Comes Out to Play First Date DisastersWhen the Cat Comes Out to Play First Date Disasters
Tiger King via Netflix / twitter via @Ellrn_BESS

More specifically, the cat owner told his date that they absolutely needed to wash his cat, and she did it. Let's just hope she wasn't allergic to cats, or else that could've made for a pretty uncomfortable evening. On the plus side, at least the guy didn't have a criminal record or anything like that, right?

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One Step at a Time, Sir

Meeting the family is a significant step in any relationship, and it's essential to go about this in a way that makes both partners comfortable. With that being said, telling a woman on the first date that you'd like her to come to your grandmother's house for Christmas - six months in advance - might scare her off.

One Step at a Time, Sir First Date DisastersOne Step at a Time, Sir First Date Disasters
Getty Images via Kevin Mazur / Twitter via @officialMegann

It's sweet that he already imagines a future with this girl, but maybe he should tone it down a bit; What do you think? Perhaps these two should try to make it through the first date, see if they're even compatible, and take it from there. Who knows, maybe they'll be spending Christmas together in the end.

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'Normalist' Girl Yet

It's no secret that after going on a first date, many people run to tell their friends about it and reveal all of the juicy details. When this guy decided to introduce his date to his friends immediately after meeting her, evidently, he only had nice things to say about her.

'Normalist' Girl Yet First Date Disasters'Normalist' Girl Yet First Date Disasters
Getty Images via Getty Images/Handout / Twitter via @k_leigh

He claimed she was the "normalist girl he's found yet," so that must be a good sign, right? Well, it likely boosted the girl's self-confidence, but what does that reveal about his past relationships? More importantly, could this mean he's a weirdo? Who knows if this girl even gave him a second chance after that!

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Fish Have Feelings Too, Apparently

Before we go any further, we'd just like to remind you that fish have feelings. So, when this woman went on a date with a vegan, their clashing meal choice sparked some awkward conversation. After eating fish tacos, she was surprised when her date started talking about fish and their feelings.

Fish Have Feelings Too, Apparently First Date FailuresFish Have Feelings Too, Apparently First Date Failures
Getty Images via Robert Kamau / Twitter via @amy_beds

Evidently, he wasn't too pleased that his date chose to eat the fish rather than adhere to his eating habits. Do you think this means there won't be a second date? But hey, at least this woman was treated to some delicious fish tacos and a thought-provoking conversation.

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Thanks for Pointing Out My Flaws

When it comes to meeting someone on a dating app, the truth is, you never really know what you're in for when you meet the person in real life. People are often surprised when their date doesn't appear the same in-person as they did in their photos, especially when their profile said six feet and they're really 5'3.

Thanks for Pointing Out My Flaws First Date DisastersThanks for Pointing Out My Flaws First Date Disasters
Getty Images via Juan Naharro Gimenez / Twitter via @Knitlucy

In this case, this man had relatively high expectations for his date's appearance and was pleasantly surprised to see she wasn't as perfect as he'd expected. However, the way he went about telling her didn't turn out very well. He simply pointed out all of her flaws, and something tells us she was done with him after that.

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Is That You?

Getting set up on a blind date can be extremely nerve-wracking, especially when you don't even know what your date looks like. How are you supposed to even find the person in a crowded venue? Coincidentally, both the man and the woman in this situation nervously waited outside the pub for one another.

Is That You? First Date DisastersIs That You? First Date Disasters
Getty Images via Jim Smeal / Twitter via @DeborahAharoni

When this guy came to the realization that he may or may not have been standing next to his date and blatantly ignoring her for 30 minutes, he figured he might as well text her. And evidently, the woman to his left was indeed his date, and by the sound of it, he hadn't made the most remarkable first impression.

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Disappearing Date

Not many things are worse than being stood up on a date, but this situation might come close. After the guy ate his expensive meal, he headed to the restroom, and from that point on, things didn't exactly go as he'd planned, hence why he never returned to the table.

Disappearing Date First Date DisastersDisappearing Date First Date Disasters
Emily in Paris via Netflix / Twitter via @mc_arthur123

After a while, the girl came to the retaliation that her date would probably never come back from the restroom, and clearly, he'd had ulterior motives. So, not only was this girl ditched mid-date, but she was also left to pay the bill, and apparently, it wasn't exactly a cheap meal.

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Apparently, He's Married

Just take a moment to read this tweet, as many things from this first date seem rather odd. First, this woman's date took her to a frog jump festival; Does anyone even know what that is? What exactly does one wear to this type of event? But wait, it gets worse.

Apparently He's Married First Date DisastersApparently He's Married First Date Disasters
Getty Images via Kevin Winter / Twitter via @MrsMZ2u

Suddenly, the man demanded that they leave early, and the reason didn't have anything to do with the frogs. To his date's surprise, he was still married, but not happily. Believe it or not, his wife had a restraining order against him, so it looks like the evening ended far earlier than expected.

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Hike to Rejection

Ever since social distancing became the new norm, people have learned to get creative when planning dates. This guy decided to take his date on a scenic hike, but once they reached the top, things took a turn for the worst when he revealed some shocking news.

Hike to Rejection First Date DisastersHike to Rejection First Date Disasters
Getty Images via Bauer-Griffin / Twitter via @suziechism

While this guy's date did her best to pretend she was having fun, he was getting back with his ex via text message during the never-ending hike. So nice of him to tell his date after they'd made it to the top, right? You'd think maybe he would've told her before they'd left ground level to spare her the exhaustion.

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Unfortunate First Kiss

Ahh, the endless wonders floating through a person's head before their first kiss. You're probably just hoping your date brushed their teeth to avoid giving you the scent of their unfortunate breadth. Evidently, her date's hygiene turned out to be the least of her problems for this lady.

Unfortunate First Kiss First Date DisastersUnfortunate First Kiss First Date Disasters
Getty Images via Anita Bugge / Twitter via @Nichelle136

The guy leaned in for a kiss, and out came a loud, nasty burp. What would you do in this situation? I mean, we all have to let it out at times, but on someone else's face might not be the best place. If they had a genuine connection, then maybe the woman let the burp slide; Who knows!

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Caught Red-Handed

It's always interesting to see how a first date plays out, especially when you cook them dinner after knowing each other for about 10 minutes. In this case, the guy was thrilled to put his culinary skills to the test and make his date a delicious meal, but she wasn't exactly willing to be his sous chef.

Caught Red-Handed First Date DisastersCaught Red-Handed First Date Disasters
Instagram via @mindykaling / Twitter via @WallysVoice

Instead of tossing the salad or even enjoying a beverage on the couch, the woman started snooping around. All of a sudden, the guy saw her ripping through his mail. Hopefully, he had nothing to hide, so this wannabe investigator realized that she was on a date with a kind, innocent man, after all.

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The Key to Remembering Your Date's Name

It's true, some people just can't remember names easily, which can be hard on a first date. But, this guy was proactive about the situation and resolved it before making his date feel bad. Thanks to good old Starbucks, all customers receive their coffee with their name on it.

The Key to Remembering Your Date's Name First Date DisastersThe Key to Remembering Your Date's Name First Date Disasters
Getty Images via Gotham/Contributor / Twitter via @noodlez56

Now, that's what we call avoiding the problem, don't you think? Let's just hope the guy's date didn't pick up on his little trick, and the barista didn't reveal that Mr. Clever does this with all his dates since he meets too many girls to remember their names.

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Desperate Times Call for Desperate Measures

Going out for a sit-down dinner on a first date can be risky. Imagine if 20 minutes into the date, you realize that you have absolutely nothing in common with this man. But you can't leave yet, because the food still hasn't arrived. In this type of circumstance, creativity and desperation often take over.

Desperate Time Call for Desperate Measures First Date DisastersDesperate Time Call for Desperate Measures First Date Disasters
She's Out of My League via DreamWorks Pictures / Twitter via @MummeWummie

This woman was absolutely desperate to get out of this date, so she consulted the waiter for some assistance in her plan. For the price of $20, the waiter gladly spilled this woman's drink on her, giving her the perfect reason to leave the restaurant. Hopefully, she took her own car and didn't have to drive home with her date.

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Quite the Introduction

First impressions are key, which puts a lot of pressure on making a memorable entrance for some people. Instead of driving a car like any ordinary guy, this man showed up at his date's house on a skateboard; At least he'd planned to. Unfortunately, though, the driveway had a few too many bumps.

Quite the Introduction First Date DisastersQuite the Introduction First Date Disasters
Getty Images via Rich Polk / Twitter via @SJSchauer

You can probably guess what happened next; The skateboard got caught in a crack, the guy flew into the air, and then slammed on the grown. So basically, his date watched him lay unconscious on the ground before even exchanging a sentence. That's certainly one way to make an entrance!

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