Hilarious First Date Stories That Took an Unexpected Twist
The Most Painful First Kiss Ever
Ahh, awkward first dates. They never stop. Could be an amazing first date where you make a great connection and everything’s running smoothly until you say goodbye. That is the moment of truth. Two people like us, do we hug and wave, or go in for the kiss? This dude leaned in for the kiss, and things went horribly wrong. He ended up accidentally elbowing his date in the face.
The woman seemed quite cool about this awkward development and didn’t hold it against him. However, they got married!
21-Year-Old Who Wanted to See an R-Rated Movie, But His Mom Said No
A movie is a relatively standard first-date idea — albeit a bit of an awkward one, as spending an entire film in silence with a stranger is obviously less than ideal. Anyway, this couple landed up going on a first date when they were both 21 years old. She chose the film, and when he found out that it was R-rated, all he could think of doing was call his mother.
He made a call to his mother to see if he was allowed to go see an R rated movie, she said no, the two went home, and thus the most awkward first date ever recorded in human history was over sequentially second by second.
She Went On A Date BUT Her Date Took His Parents Uninvited
First dates can be extremely awkward. It is overwhelming to meet for dinner and constantly converse because you never know what to say. Nevertheless, even more awkward when you bring your date at the same time with his parents. And no, this isn’t a date for children; this is a date for 25-year-old grownups. Who thought it would be nice to take their parents with them — and without warning?
KellyScicluna/Twitter | austin4site/Instagram
The cherry on top was when the mother asked the girl if she was going eat all her food and then immediately whipped out tin foil to pack away the food to take home.
You Should’ve Preceded That With the Dead Body, Dude
A funeral director probably isn’t the best person to try to date, or at least someone you’d probably like to date anyway, just in life in general. This a super heavy topic and is probably not very conducive to keeping optimism alive on a day to day basis. This isn’t exactly a first date story, but hey, one of the earlier chapters of the dating timeline. She climbed into a car with her date — a mortician — and he nonchalantly said he had a corpse in the trunk of the car.
This is still a little disconcerting and weird to do even if it is undoubtedly a whole lot less worrisome than if some stranger was talking to you.
When your date and your waiter went on a date together last night.
It nearly reads like a too-crazy-to-be-true story. At his dinner table on a first date for two, the waiter suddenly looked at the man confused and asked, When you stopped being gay? We had a date last night.” Unfortunately, you really never hear the story past that, so who knows how it played out after that.
mc_arthur123/Twitter | mandiballaroberts/Instagram
Like this sounds like the kind of prank you would pull on your ex to get back at them. Since, who is dumb enough to show up at an ex-crush’s workplace?
Disclaimer: It Is Not Pee
On a first date, plenty of guys get all kind of jittery. You never know how you are going to react to a situation—you can even surprise yourself with what you do in a given moment. The person was driving into the driveway of the woman he was about to go on a date with when he poured soda over his pants. As soon as he opened the car door and she opened the back door, the first thing he said was, “It’s not pee.”
PatrickAH81/Twitter | ohheyyitsashleyl/Instagram
In this case, it’s just not enough to say it’s not pee. So maybe we feel fine that it’s not pee, but what on earth could it be? He ought to have said, “I spilled soda”
Bad Humor Is a Red Flag
Pulling pranks on any date are a risky business and even a pretty risky business to do when in a long-term relationship. But when the prank occurs on a first date, well that’s just downright shocking. Another woman is on a date, and the guy says you have got to smell my food, I think it is off. This was strange enough, but then he did the worst thing.
herstory07/Twitter | abbyrogers30/Instagram
And then he pushed her face in to the food, which he thought that was the sort of funniest, practical joke. I cannot even picture how maddening that would be for the woman and how any guy could possibly believe that this was a good concept.
At Least This One Turned Out Okay
Sometimes people go on a date with someone without necessarily searching for the same thing. Other times, they simply want some company during routine activities — maybe someone to see a movie with, or go out to dinner with. A man ended a date with this woman by being brutally honest, and telling her that he “only went out because he had nothing better to do.
And somehow the lady wasn’t truly upset by that (perhaps that’s why she continued on the day too), and they went exist magnificently ever after. Perhaps they were just both married because they had nothing else going on.
Bold Opening Line, Sir
Opening a date by declaring that one has literally nothing, followed by a request to borrow $10 so that the borrower could purchase a drink from a convenience store, is already bad enough. Going into the store to then also purchase a scratch-off is another deal entirely. But then asking his date to spend his winnings on a trip to a strip club and waiting for her to arrive took it up a notch.
Chelseathrash1/Twitter | leebone66/Instagram
For fucking sure, this woman was not going to be going to a strip club with this man for a first date. He could take that $60 and go have a lap dance at the strip club alone.
A Relaxing Date With Her and Her 10 Friends
This lady really did not know how to schedule a date, or plan her life. This woman went on a date with this man and he was greeted by a surprise 10 of her girlfriends, who didn’t even know he was coming. Also, she was wasted blacked out and introduced him to all of her friends with the wrong name.
She also told them out of nowhere that she confused the names of her United States of America; they were the names of the dude she was going out with tomorrow.
No second date for the government to eavesdrop on
If you came to a date and found the other person had their phone taped up you probably would be quite shocked. Has it just fallen off a very high cliff? Maybe they did not want to get a shell for the phone. This woman’s date didn’t seem to fit all of these answers. When she questioned why it was taped at the receptacle, he said “Because the government is listening.”
klaracee91/Twitter | not_too_sue/Instagram
And the funniest part about this is that he legitimately thought that this tape would even work in preventing the government from hearing him—it was just tape for fucks sake.
Well, Then — I bet There Was an Awkward Pause After That
This guy came to the date with this very attractive girl and expected her to just be a bimbo. We assume he thought that she was hot but dumb, which begs the question of why he wanted to date her in the first place. Anyhow, she began talking about science, religion, and humanity, and he was shocked. He was so appalled he even had the gall to say it to her face.
actualjaneway/Twitter | chelcsindn/Instagram
He said I never thought you would be smart. What planet did he think it was OK to say something like this? Which one of you does that actually seem appealing to?
He Was Matched With A Grandmother of a Girl
You just cannot beat a classic old catfish. It’s a pretty normal and simple thing to do, actually, when you “meet” people online. How hard is it to find a few faces and post them to a website? NEWS FLASH — this woman catfished herself to get a date for her grandma. At the one point, she told the man to come to her grandmother’s house for the date, then she just left the two alone together.
SethShaffer/Twitter | therealoliver6060/Instagram
This is not necessarily the best idea for trying to match someone. Um, maybe test the waters a little before throwing grandma at someone?
Just a Little Trip to the ER
Nothing like that first date ending in an ER visit. All is good; you are vibing and having a good time, and boom, everything just turns out to be a disaster. And when this lady strolled into the bar and discovered that her shoe was filling up with blood—she had stubbed her toe. After the bleeding did not stop, they ultimately had to go to the ER for a few hours.
And yet somehow, after getting ten stitches on her newly broken toe while this man spent eight whole hours with her in the ER, she ended up going on a second date with him!
“This Isn’t My Car”
There is a long list of embarrassing things you can do on a first date, and sitting in the wrong car is pretty close to the top. This was a woman who wanted to demonstrate she was an independent woman, entering the car herself before he had the chance to open the door for her. And instead of demonstrating her independence, she demonstrated a slight degree of recklessness trying to get into the wrong car.
annabanna0626/Twitter | Instagram/zai_barr96
The most frustrating part is that that car was also unlocked. How likely is this going to happen? One would imagine that people keep their car doors locked unless they had a passenger in the front seat.
Okay, but why is this one sort of cute?
You feel free, focused, and unencumbered, and nothing makes your heart sink like walking into a restaurant and suddenly having the idea that you forgot what your date looks like. Now, admittedly, you only met them extremely briefly before this, so there’s no real expectation for you to be able to remember too much, but having to go table to table searching for the man is also a pretty bad look. Must have been quite the sight seeing this guy sitting at the table waiting for her.
A couple of minutes later, he motioned to her to come on down. That she was not approaching him right away was probably also confusing for him in the beginning.
So Long As You Wrote the Check, We Don’t Mind This One
Sushi is one of those things that can leave you scratching your head when it comes to ordering. The whole idea of it, in case you don’t get it, are at a loss for what, and how to eat it. An actual first date at a sushi place where this dude figured thirteen rolls was an acceptable amount of food to order. What they failed to understand, however, is that a roll was not a single piece but the whole lot.
foreversmiling2/Twitter | iam_zinhlentulay/Instagram
Also a little weird is the fact that the date, the waiters, or even this person themselves didn’t put a stop to this stupid decision somehow. They must have known they did not know.
Peeping From Behind · Just Her Dad
Okay, let us say you are on a first date with someone. So you start your movie sit down, and then assume you are all set. And suddenly, you realize that your date can’t stop looking at the person behind her—so many times, in fact, that the only thing you can think about is: wow. Towards the end of the night, you’re like, “Why was she staring at that one guy the whole time?” and then you ask, and you realize the whole time the guy had also been watching the film and was her dad.
Will_Alderson/Twitter | jaredwho/Instagram
Do you think her dad was out to chaperone the date or was it one of those freak coincidences where they went to the same movie at the same time?
His Family Thought he was Coming to Meet the family; little did they know, they were the Family
Classic rom-com trope. You have two people who are dating each other, and things seem to be going well. And then something—somehow they discover they are really related. Sounds like something from a movie never to happen in real life, but this story will prove that it did. On the way to their rendezvous, they paused at a family BBQ and somehow learned that they were cousins.
Feels like this is just stepping the line for some morals. They’re technically third cousins, but also related; that’s just way too creepy to keep going with dating.
Still, You Know It Was a Strange Evening when You Found Yourself at Your Date’s Ex-Wife’s House
First-date stories probably top the list of the most weird ones ever to be found on Tinder dates. So this person is dating a guy from Tinder, and here the date(s) began! They had a bit too many drinks and somehow ended up at his ex-wife’s place. They sat and talked while she picked out a wedding gown for the ex-wife to marry another man. Talk about a crazy story.
clur_sands/Twitter | throuple.life/Instagram
Only someone severely intoxicated would put themselves in a position where entering a place such as this would even seem like a good idea. That’s something that could happen at any time, but on a first date, it’s kind of insane.
Alright, Hint Taken
Not everyone is a fan of kissing on a first date. To them, that might be seen as pushy or impolite. But then again, how can you avoid it when, at the end of the date, awkwardness seems ready? With everything in her power to avoid that kiss, this woman oped to coat her slice of pizza with garlic powder to ensure no kiss was happening.
BattleOTBeltway/Twitter | palatinipizzeria/Instagram
But she likely didn’t need to tell him everything—what her plans were. Just seeing that the mount of garlic went on the pizza was probably sufficient.
Mind The Further To Whom You Text
IMO, nothing is worse than sending a text to the wrong person. In this case, it could be worse than texting the wrong text. This one just went out on a date when the friends texted the man to ask how it was going. He said he regretted asking her out. Except that he didn’t send it to his friend; as he thought, he sent it to his date.
The rest of the car ride home was understandably awkward. At this point, what is there to even say? It’s just too awkward.
Ouch! (Figuratively) #ThisOnesGottaHurt
Alright, well, this one is probably a bit of a winner for the winner’s circle. The rest of the date doesn’t need any of the backstory or context. It might have been the best date ever but still ended (or maybe even more appropriately started) with this man running her over. That is virtually impossible to recover from in any case. All you have to do is pray that in the attempt she was not very hurt.
This dude wasn’t mincing words; a second date was smack across the hood of his car—well, his car in her, not to pun intended, undercarriage. Well, to be fair to the dude, there’s no way in hell, unless you really hate conversation, even this loser was getting a second date after hitting her.
Could Have Passed It Off as a Magic Trick… Started To Say Weird, Still Weird
Everyone wants to avoid looking twitchy and uncomfortable on a first date, but sometimes it’s unavoidable, particularly when a little something is stuck in your sweater. You do everything you can to reel it out, but it is taken with additional work and nothing else but to pull your sleeve way up and rake it out. You are left pulling out the underwear of your mom. But we are delighted that he started doing his own laundry.
At that point, there is nothing you can do other than accept that the date was an epic fail (sorry, boys!), try to work out how those panties found their way there, and move on.
Now we have cameras on smartphones, thank God!
Now, the cell phone is ubiquitous, and who can remember what dating was like before them? To think that people simply had to commit addresses and times to memory and there was no way to check that the other person would actually turn up to the date is bonkers. He felt the no cell phone struggle when he showed up to the wrong house, and an older couple invited him in to help him look for her name and address in the phone book.
Todd doesn’t record what happened at the end of this date. Did he ever find the woman? Did they even ever see each other on a date? Did he become friends with this old couple?
A Gassy First Date
When you date someone, you eventually put forth you’re A game on your first date—and most, at least, try to cover up their bodily functions for well over into dating for a few weeks. On the first date, you probably aren’t discussing your burping, farting, or bathroom schedules with the other person. Yet this lady has recently been put on a fresh prescription medication, which made her burp and pass gas during the entire initial date. The man was not the least bit startled; they had a terrific date and eventually got married!
In fact, this woman deserves some credit for even going out on a date in the first place, knowing that this was the state of her digestive and gas systems.
When I Knew He Was a KEEPA →
I don’t think there would be a human being on the planet who went wow! I was really impressed to see an onion born from the nose of my date at the first meeting. That’s definitely not the most romantic thing that can play out. But Maureen wasn’t bitter about her date choking on an omelet. According to her, he then blew a chunk of onion out of his nose during the process.
Looks like that also was not enough to stop the love and then the romance. They got married and probably had an onion-themed wedding.
Is It a Joke or a Nervous Breakdown?
When going out, generally during first dates, nerves can be overwhelming. As much as you try to be chill and relaxed, there are just moments where you can’t help it and end up losing control of either your body or your tongue. Suddenly you start to sweat like a madman, or you may say very stupid things. His very first date, however—well, this woman appeared to win the cake with his silly comments.
On one date, when her fellow complimented her on a nice smell, she replied, “Thank you, I use both of my nostrils.” She wasn’t attempting a joke; they were past that point; the best option now, though, was to feign one.
Consider the case when your date is triple booked.
But there is a thin line between being productive and not wasting your time and just complicating your life. How fucking busy does one need to be when attempting to have two dates at the same time, in the same restaurant, with two different ladies? You have to know by now that there was no way that was going to fly, even if you made up seemingly random trips to the restroom a thousand times.
Everything he did seemed suspicious, but thankfully the waiter was accountable. Definitely an odd sight—a guy trying to be two places at once.
You Go, Girl!
From big blunders to subtle mishaps, a first date has many, fine paths to disaster. You can be timid and silly or make a mess of yourself. However, when someone is simply straight-up rude from the very second you meet, it is simply inexcusable. His first sentence to his date was, “I thought you would be thinner.” In not-so-polite terms, this woman did what he so rightly deserved.
One cutting sentence formed her retort: “I thought you were going to be smarter.” Snatch his glass and dump it into his lap. What is even more amazing is that she didn’t even go for the looks, she attacked him on the level of his intellect.
What Are the Odds?
There is no such thing as a blind date that loses, right? You’re relying on friends to be acquainted with you so well that they can select a person for you to go out with This could be a love story, and it could be a horror story. But this one here was just a happy coincidence. The thing is, this woman showed up for the date a little down because she had just gotten an expensive traffic ticket earlier that day. What she was unaware of was that he was the officer who gave her the ticket.
Just imagine what she thought when she showed up at the meetup spot and saw the same cop, but then to even make matters worse, it was her date?
That is not a blind date, that is a stranger date
You can read part one here (about why they are dangerous). If you were ever thinking of going on one. This dude was just waiting for this girl to arrive to their blind date, Then one day a woman showed up, sat down at the table with him and ate. The entire meal she spoke not a word, and then got up and just left, without any explanation.
Just when she left, he got a message from the real woman that she couldn’t make it, So turns out, he had dinner with a total (weird) stranger.
Pre-wedding jitters: What beats being stood up at the altar? Getting Left at Taco Bell
It’s bad enough that someone would take someone on a first date to Taco Bell. Not the best date idea, but hey, budget, right? So, the only option. Definitely do not leave them at Taco Bell after the date, though. No, you don’t need to take someone home, but there is also no need to leave them there alone.
At least you can be sure that there was not a second date for this guy afterward. Well, you can only hope, not because he didn’t deserve it.
Perhaps it was one of those anxious laughs?
Right, well as much as I know this sounds like an incredibly awkward and somewhat childish thing to do, it’s not as bad as it seems. It completely kills the mood if someone asks you if they can kiss you—and very few people like to be asked. On the other hand, some people likely won’t care. No one likes a pushy person in dating, and it is better safe than sorry.
For this instance, the woman giggled the man’s way when he asked if he could go in for a kiss. Maybe it was plainly obvious that she too was into me.
Binside: Always Wipe Your Mouth After You Eat Ranch
It might be the most disgusting first date story on the list. First kisses are a dangerous game; you want it just so, and the moment to be sweet and perfect with moonlight scattered about it like constellations. But the same mentality is not on the same page for everyone. Sure, ranch dressing is disgusting to anyone who likes to cover their food in some sort of white sludge, so that girl got what was coming to her when he went in for the first kiss, and she had a mouth full of ranch dressing that could not appeal to anyone, no matter how much they were attracted to one another.
You can only pray she was inebriated and might be embarrassed by her actions later. No one wants ranch dressing in their mouth for a kiss, and no one would be ok with that even if it is a first kiss.
At Least He Was Consistent
I guess you can only try to get so drunk before a date you can barely function, right? So this guy was on a date with a girl and left to use the toilet for a minute. When he came back outside, completely forgetting that he was on a date, he approached the girl he was with and used every pickup line in the book. At least his taste has stayed consistent!
You might say it was more of a silly story than a horror story. Still, he’s obviously quite attracted to this lady, drunk or not.
Not the Way to Kiss a Human
While it’s completely normal for you to kiss your pet and share kisses with them, it’s not normal to think that you’ll kiss a human in the same way that you would kiss a dog. This woman was out on a date with a gentleman, and, when it was time for him to leave, he went in to kiss her. But it was not just an ordinary kiss. It was a ‘puppy trumpet’ kiss—where he blew into her mouth and nose.
The Parallel Parking Fail
New Delhi: Parallel parking is an extremely pressurising activity. Too many people watching you and you fail one more time and you feel like a complete loser. Take all the regular stress of parallel parking and add in your date waiting for you and watching you. This man also attempted to park three times, without success. The third time, he just whipped it out then sped away never to return.
He was still too humiliated from this debacle to confront her. He decided instead to leave her in an awkward predicament.
Has Anyone Ever Bullied You Into Dating Them? She Has
Which is precisely the reason that you should never organized a surprise date for someone. Get help from your friends and family if you are planning something good, always tell them where you are going. The date this woman was about to go on had no idea who she was. It was something far worse than just the going to a Vikings game with a bunch of friends. But so she showed up wearing a jersey and face paint.
Worse than the shock of the fact that this was a date was that it was a date at a 5-star candlelit restaurant.
