45 First Dates That Went Terribly Wrong Dished To Jimmy Fallon

By Larissa C


Dating is one of the best things in life. Having the opportunity to go out with the person who makes your heart skip a beat? That’s priceless. But dating is not all roses — sometimes it’s kind of hard to find the right person, and it’s even harder to go on a perfect date! Lots and lots of people go on awful dates, and if there’s one thing we all know about bad dates is that you don’t forget them quickly. The only good thing about these kinds of dates is that, once the initial trauma is over, we get to share our stories with friends and have a good laugh. If you just had a bad date, don’t worry — you’re not alone! In fact, if you feel like reading other people’s stories or sharing your story with others, there’s even a Jimmy Fallon hashtag challenge on this very subject: #WorstFirstDates. We chose some stories shared with the popular TV Host for this article, and we’re going to show you 45 first dates that went terribly wrong!

Do you really need permission?

Going to the movies is kind of cliché, but it is also one of the best things to do on a date. Watching a movie allows you and your date to talk about your shared interests and bond over them.

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The only problem with going to the movies is when your date needs to call his mother and ask for permission to watch an R-rated movie. This is exactly what happened to Twitter user Mojo Jojo. Usually, this wouldn’t necessarily be a problem, but the issue is that her date was a 21-year-old man — which is old enough not to need permission from his mother!

Meeting the family already?

When we’re looking for long-term partners, one of the things we take into account is whether this person has a good relationship with his or her family. You can tell a lot about a person based on their relationship with parents and siblings, after all.

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Kelly’s date had a great relationship with his parents, and that was definitely not a problem. Well, it wasn’t a problem until he decided it was a good idea to bring his parents on his first date with Kelly. And if that’s not bad enough, his mother didn’t even want to let Kelly finish her meal!

Wait, what?

Even though we try not to pry, we can’t help feeling curious about our dates and wanting to learn more about them. On most dates, people usually start getting to know each other by first asking what the other person does for a living.

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Have you ever imagined yourself dating a funeral director? Well, that’s exactly what happened to Twitter user Christine Woolslayer. While the profession itself is not a problem, it becomes an issue when your date picks you up in his work vehicle, and there’s a body in the back of the car!

Two-timing is so out of season!

When we go on a first date, there are 50% chances that this date might be perfect, but there are another 50% chances that this date can go in the worst direction possible. Even still, we try our luck and go on dates in an attempt to find the love of our lives.

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However, there are some things we can’t change even if we met someone incredible and are having a great date. One of those things is changing someone’s preferences in men or women, as it happened with Michelle. Much to her surprise, her date had gone out with the waiter the previous night — and the guy showed him no mercy as he exposed Michelle’s date in front of her!

A classic accident!

When we go out with someone for the first time, we desperately try to make a good first impression. This first impression will either make or break your relationship with that person, so it’s pretty understandable why some people get really nervous on first dates.

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Spilling a drink on your pants is a classic accident and happens to the best of us. But this accident is even more inconvenient when it happens right as you arrive at your date’s house. Looking like you peed your pants certainly doesn’t leave a good impression — but maybe this is a sign that you shouldn’t be drinking soda or anything else while driving!

He just couldn’t help himself!

Another classic date night is going out for dinner with your date. Some of the best conversations happen when you’re sharing a meal with someone. Plus, a dinner for two can be quite romantic, depending on the location and the setting.

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Going out for dinner is also a great way of getting to know the other person — and it helped this person dodge a bullet on her first date with this guy. Pranksters can be quite funny, but sometimes they take things too far, as this guy did. You just don’t push people’s faces in your food, sir, especially not on a first date!

Oh, thank you for the time, Robert!

If there’s one thing that we look for in a relationship, that thing is honesty. While lots of people consider love as the most important factor in a relationship, honesty helps a great deal in making a successful marriage and should be treated as equally important as love.

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But sometimes, too much honesty can hurt — especially if you’re as blunt as Robert was on his first date. Saying that you took your date to the movies because you didn’t have anything else to do is certainly unorthodox but, apparently, it worked for Robert and his date, as they’re now married!

Do you have no shame, dude?

Let’s talk about cringy dates. Sure, most dates we’ve talked about so far have been cringy dates. But none of them were nearly as bad as this next one. Not only was the guy shameless, but he even had the gall of getting upset by the end of the night!

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First off, there’s absolutely no problem in splitting the bill on a date. The notion that the man should pay for the meal is truly outdated — but showing up on your first date with no money at all? That’s just ridiculous! And if borrowing money from his date was not bad enough, this guy got upset that Chelsea didn’t want to go with him to a strip club. Yeah, this may be one of the worst first dates ever!

Accidents happen!

Remember what we talked about making a good first impression on a first date? Now imagine doing something clumsy and embarrassing yourself in front of your date. When stuff like that happens, you may feel like that will be your first and last date with that person.

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That’s what happened to Mike. He was so nervous during his first date with this amazing woman that he ended up elbowing her in the face. He was obviously worried about hurting her, but he also worried about ruining his chances with her. Luckily for him, the woman saw right through his nervousness and stuck with him — they’re now married and living happily ever after!

Call me by my name!

Bad dates go one of two ways: either you do something embarrassing in front of your date, or it’s the other person who does something to ruin your first date. To be honest, we don’t even know what’s worse — all we know is that this next date sucked!

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There are so many things that went wrong on this date. First of all, what kind of person brings 10 friends to a date? And who in their right mind gets wasted before meeting their date? And if those two things were not enough, Chris’s date called him by the wrong name. To make matters even worse, it was the name of the guy she would be seeing the following day!

They’re Watching

When we meet someone online, the truth is that we can only get to know a part of them. It’s much easier to withhold information when you’re just texting someone. Sometimes, this is not even intentional — some subjects just never come up.

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The problem with talking to someone online is that, when you meet in person for the first time, you may be surprised by what you see. That’s precisely what happened to Klara. She had no idea that her date believed in the conspiracy theory that we’re always being watched by the government!

Wait, are you telling me that women can be intelligent?

While we’re on the topic of online dating, another issue that can occur when you meet someone online is that the spark you feel may not be there once you meet in person for the first time. And maybe that’s what happened during this date:

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The guy she met online was late for their first date, which is awful already. And then he didn’t seem eager to have a conversation with her. But to make things truly bad, he had the audacity of assuming that she wasn’t intelligent, which is an extremely sexist thing! It’s kinda sad, really.

Maybe you should stick to dating people your own age!

As creepy as it may sometimes be, it’s not unusual to see older men dating much younger women. While having an age gap with your partner is not wrong, you probably should avoid dating someone who’s 15+ younger or older than you.

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Seth had to learn that he should stick to dating people his own age in the worst way possible. When he met a younger girl, he was probably thrilled to show her off to his friends — but the girl wasn’t having it. Instead of going out with Seth, the girl set him up with her grandmother. What a bad date that must have been!

A date to remember!

Imagine that you meet an amazing person, and you hit it off right away. The other person asks you on a date, and you’re thrilled to be going out with someone who made your heart skip a beat right from the get-go.

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Alida got to experience that, but things started going downhill from the moment she stepped into the bar where she was to meet her date. She stubbed her toe as soon as she got there, and, unfortunately, she got a bleeding and broken toe and ended up in the ER. Luckily, her date noticed how strong she was and set up another date!

That’s so…unflattering!

One downside of online dating is that you have never seen that person in real life by the time of your first date. Who knows what they actually look like? For all you know, they may be completely different from the pictures you may have seen.

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But even if they look exactly the same in pictures and in person, there’s still another issue. You may simply forget what the other person looks like! Cassidy was sitting at the restaurant, waiting for his date to arrive. When she did, he noticed how she kept walking around and looking for him. He then realized that she forgot how he looked like. We guess that he probably wasn’t flattered by this!

Double embarrassment!

Embarrassing yourself in front of your date is bad enough. But embarrassing yourself in front of your date and other people? That has got to be one of the worst feelings ever! Unfortunately for this Twitter user, that’s exactly what happened to her.

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There’s nothing wrong with being an independent woman, but there’s also no problem with letting things happen naturally. Anna tried to show this side of herself by entering a car without waiting for her date to open the door for her but ended up getting inside someone else’s car. Who knows if her date was really going to open the door for Anna? If only she had waited, she wouldn’t have embarrassed herself!

Did no one tell her?

As crazy as it may sound, some people have never eaten sushi in their lives. Some people simply don’t like the idea of eating raw fish, but other people really just never had the opportunity of going to a sushi place.

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This woman went to a sushi restaurant for the first time on a first date. She wasn’t aware that a roll of sushi is actually 6 individual pieces of sushi, and not just one. We can only imagine how surprised and embarrassed she was when 78 pieces of sushi were delivered to their table!

Not on my watch!

Some people are way too attached to their families. While having a great relationship with your family is not necessarily a bad thing, it’s important to keep in mind that the excess of everything is bad. Will’s date still has to learn that, apparently.

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Imagine that you’re on a date, and this happens to you? We’re certain things would be awkward from the minute you saw your date’s parent watching the two of you. Remember the guy who brought his parents along on his first date? Well, he would certainly have made a great pair with this girl!

That must have taught him a lesson!

When we’re feeling nervous, it’s not unusual for us to start fidgeting. That’s our body’s natural response to nervousness. Some stressful situations, like going out with someone for the first time, lead people to fidget. But if we notice that someone is fidgeting too much, we start getting suspicious.

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Marc was the one who was fidgeting, and his date was probably the one who was getting suspicious. He was fidgeting because he could feel something funny in his sweater. We can only imagine how embarrassed he was when he found his mother’s underwear was stuck inside his sweater. At least now he’s doing his own laundry and not waiting on his mom to do that!

How in the world did this happen?

If you’ve ever used Tinder, you’re probably aware that we can come across all sorts of people on that app. It’s also common knowledge that it’s pretty hard to find the love of your life online, although it’s not impossible.

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When we say you can meet all sorts of people on Tinder, we really mean that. Claire found a divorced guy, and they went on a date — nothing unusual here. The weird part of the date started when they got too drunk, and Claire’s date took her to his ex-wife’s house!

So straightforward!

Dating is an incredibly complicated thing — especially because physical appearance is not at all the only factor that makes a difference when you’re getting to know someone. If the conversation doesn’t flow naturally or if you just can’t connect with the other person, chances are you won’t be going out for a second time.

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For Twitter user Ben Kaplan, things happened the opposite way. It wasn’t that he was not interested in his date; it was she who wanted nothing to do with him. Eating a bunch of garlic powder just to make sure your date won’t kiss you? And to let them know precisely why you’re eating that? This girl is a savage!

The Ride Back

Knowing that your first date with someone isn’t going well is one thing. It’s pretty disappointing to have a bad date, especially because our expectations are usually high. Now, hearing that the date sucks directly from the other person is a completely different thing.

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While that sounds absurd, it’s exactly what happened to Maïté on her first date. The two of them could feel that the spark just wasn’t there, and so the guy decided to text his friend about it. It turns out he accidentally sent the message to Maïté herself! Poor girl!

Wait, you have to tell us more about that one!

The craziest things can happen during first dates, but some things are way crazier than others. In this article, we’ve seen people who found underwear inside their clothes, girls setting up guys on dates with their grandmothers, people bringing their parents to a first date…but this one is even more shocking!

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Hitting your date with a car? Now, that’s not something we hear every day! To make matters worse, this guy didn’t even elaborate on his story. We’re so curious as to how did that happen or how the lady reacted. We guess they probably didn’t have a second date!

At least they were kind to you!

Have you ever thought about dating in the pre-cell phone era? You couldn’t text before the date, not even to send your address or to send your date the name of the place where you were supposed to meet. Getting lost right before the date was certainly not an option!

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Todd experienced that first-hand. He knocked on someone’s door and was surprised to find an elderly couple instead of being greeted by his date. Todd had gotten the wrong address but couldn’t simply call or text his date to get her correct details. However, we’re not sure why he’s calling this a “worst first date,” as the elderly couple was so kind to him!

Well, that’s true love right there!

Sometimes we like someone so much that nothing can stop us from going on a date with them. If the feeling is mutual, we can rest assured that this dating will turn into a long-term relationship, just like it happened to Ashley and her now-husband.

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After being diagnosed with an ulcer, the doctor probably told Ashley to rest for a bit. But the woman was determined to go on her first date with this amazing guy that she was catching feelings for. She just didn’t expect that the medicine the doctor gave her would make her burp and fart during the entire date. Luckily for Ashley, her date didn’t mind, and they’re still together to this day!

Love at First Bite

Nothing makes two people bond more than facing a life-threatening situation together. Near-death events really do bring people together, especially because it makes them realize that life is too short to not go after what they want. And maybe that’s what happened between Maureen and her date.

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If relationships are all about intimacy and knowing your partner inside out, Maureen and her date certainly checked that box! What is a better way of getting to know your partner than seeing him choke and then having an onion come out of his nose? Well, at least they’re married now, so that awful date wasn’t so awful!

Okay, lady!

Our body and our feelings are utterly amazing. How is it possible that having feelings for someone can affect the way our whole body functions? How can our heart beat faster just by hearing the name of the person we love? Emotions are amazing, but they can also make you do embarrassing things!

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If you like someone, you can get so nervous in their presence that you end up doing or saying things you never would say or do in any other situation. When Jordan’s date complimented her smell, she got so nervous that she wound up replying with a nonsense sentence. Well, at least she made the guy laugh!

What a small world!

There are over 7 billion people on the planet, yet the world is really small if you stop to think about it. Even if you live in a relatively large city, you’ll probably cross paths with one or two people that you have known from other moments of your life.

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While living in a small world is not necessarily bad, it becomes a huge problem when you find out that your date is actually your cousin, and the two of you just didn’t know about it. We guess that it was better for these cousins to find that out on their first date!

I feel like a fool!

Two-timing people is an awful thing to do, and no one should ever do that. No matter how serious or casual your relationship with someone is, you should always tell them when you’re not interested in being monogamous. Unfortunately, this next woman had to find out she was being two-timed in the worst way possible:

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Imagine how embarrassed Kelsey must have felt when she found out through the waiter that her date was simultaneously dating another woman? We can only hope Kelsey and the other woman teamed up against this guy in a John Tucker Must Die style!

This guy needs to learn how to treat women!

Unfortunately, there are awful people out there in this world, and it’s out of our control if we cross paths with them sometimes. It’s even worse when you’re going out with an awful person and just haven’t seen their true colors yet!

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First of all, commenting on someone’s weight is a horrible thing to do. And saying that from the second you see them for the first time? That just means you’re an awful person who needs to learn how to treat people well. What Catherine’s date said was extremely offensive, so he really deserved to have that drink poured on him!

Well, that’s awkward!

When we have a hard time finding ourselves a date, our friends waste no time jumping in to help us. There are countless couples who got together after being introduced by mutual friends, and a lot of these couples met on a blind date arranged by their friends.

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Linda’s friend set her up on a blind date, but it seemed like the universe was conspiring against Linda. After getting a traffic ticket, she was just not feeling like going on the date anymore. Even still, she decided not to leave her date hanging and went on the date anyway. To her surprise, her date was the same cop who gave her the ticket earlier that day. Tell us about a bad day and a bad date!

Couldn’t you at least have changed your clothes?

When we go on bad dates, it’s important that we try to look at the bright side of things. It’s not easy to do that, but even the worst moments of our lives can teach us a thing or two about life in general. 

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For Heather, the lesson she learned when going out on a date with a gambler was that she should never gamble or else she would probably end up just like him. Wrecked car, worn clothes, and no money in her pocket!

Excuse me?!

Even if you go on the worst of dates, nothing will come as close as this next date. Obviously, the guy who tweeted this was just joking — or else he wouldn’t be tweeting at all. Want to know why? Check this out:

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The date started out kind of normal if you ignore the part where the girl spoiled the movie’s ending. However, things took a turn for the worse the second the girl put on a Nickelback song on the radio. At this point, we couldn’t even think of a worse outcome for this date anymore. Not even the murder part could top having to listen to Nickelback.

This could make for a great thriller movie.

Imagine that you’re at the restaurant waiting for your date to arrive. It’s a blind date, so you have no idea what they look like. Suddenly, someone approaches your table and sits down. You eat dinner together, no words exchanged. Once the food is gone, the person leaves as well. Later that day, you get a message from your date apologizing for not making it to dinner.

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Sounds scary, right? We get chills just thinking about something like this happening to us! On the other hand, Scott knows exactly what we’re talking about — after all, it happened to him. If we were in his position, we would turn this experience into a script and sell it to a movie production company!

Again, girl?

A couple of pictures ago, we talked about a girl who went on a date with a gambler. While we thought that was the worst date of her life, that is actually not true. She’s had worse dates! The same girl recounted the story of another date she had the misfortune of going on.

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One date with a gambler, one date with a convicted felon. Can we just say that Heather has a horrible taste in men? While there’s nothing wrong with serving time in jail — as long as you’ve repented your actions —, to talk about your time in prison on a first date? That’s so not cool!

Hey, people, don’t be cheap on your first dates!

Taco Bell is a great place if you want to eat relatively good food and not spend a lot of money. But is it the ideal restaurant for you to have a date? The answer is no. Well, it’s not suitable for a first date, at least.

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At least on the first date, you’ll want to show off your best traits and not try to save money. This is your chance to impress the other person and get to go on a second date with them, after all! Taking your date to a cheap restaurant and then leaving them there is definitely not how you’ll guarantee a second date, though.

You didn’t have to laugh!

When we’re teenagers, the thrill of dating someone is indescribable. All we know is that the world becomes a brighter place and everything seems perfect — that’s the power of young love. But the problem with dating as a teenager is that heartbreak is also really intense.

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Kyle was probably on cloud nine when he got to go on a date with his high school crush. His happiness was soon crushed, however, when he asked to kiss his date and the girl laughed straight to his face. He was such a gentleman, and if she didn’t want it, she could just have said no!

Way to go, my friend!

Dates don’t always have to be romantic. You can have a platonic date with a friend, where the two of you just hang out and talk and have fun as friends. This girl was on a movie date with her friend when she saw two guys sitting next to them.

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Two girls, two guys — sounds like a double date, right? Well, that’s what Twitter user Marie Connor thought. The thing is: the guys didn’t know her or her friend, so you can imagine how awkward it must have been for them when Marie asked if they were on a double date simply because they sat next to her and her friend.

Well, they say it’s for better and for worse, right?

Being in a relationship means that you’ll have beautiful moments with your partner, but it also means you’ll have to face some dark moments together. If you and your lover can make it through these moments, your love will only grow stronger.

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However, going through difficulties together is something you only have to face when you’re in an established relationship. You don’t have to go through hard times on your first date, like having to kiss your date when she’s got a mouthful of ranch dressing!

This is cute…kinda.

Your first date with someone should be something special, a night that down the road you’ll remember fondly when you’re married to that person. As such, you don’t want to be drunk or do something embarrassing on your first date!

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What is it with people and getting drunk right before their first date? This guy got drunk, went to the bathroom, forgot about his date, and then tried to hit on her as if he didn’t know who she was. Well, it’s kind of cute that he was into her even when he was drunk — but the moral of the story here is that you shouldn’t be drinking before going on a date!

There’s no way you just did that!

When we think that the dates on this list can’t get any worse, we’re proven wrong. We guess that there are weird people all over the world, so it’s only a matter of time before we encounter those people and go on a date with them.

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To be honest, we can’t even imagine how Danielle must have felt when her date blew into her nose. This is disgusting on so many different levels that it’s kind of hard for us to write about it — not to mention that it sounds unbelievable. You just don’t do things to humans as you would to your puppy!

Not even celebs can escape bad dates!

When we think about Hollywood, we think of glamour, elegance, wealth — a perfect life. Because of that, it’s kind of hard to imagine celebrities doing the “normal” things that we do in our daily routines, and that includes going on bad dates.

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Well, Jimmy Fallon is here to prove that celebs can, in fact, have bad dates. And to make things worse, this date wasn’t bad because of the girl he was seeing — it was his fault entirely! Serving saltine crackers and forcing someone to play video games with you is something you would do on a date with a friend, not with a potential girlfriend, Jimmy!

Ouch!

Putting yourself out there and going on dates with people is pretty scary if you stop to think about it. At the same time that you have chances of falling in love and having a happy ending, you also run the risk of getting your heart broken by someone.

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When Rick went out, he decided to take the chance and just let things happen naturally. Unfortunately for him, his date was considering becoming a nun. What really broke his heart was that, once their date was finished, the girl told him that he helped her make the final decision to become a nun! Poor Rick!

Are you serious right now?

Before we go on a date, we keep picturing different scenarios in our heads. Things usually go really well in those scenes, and they always lead to a positive ending with us finding the love of our lives. However, the reality is way different than that.

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Leslie certainly knows what we’re talking about. After envisioning a great date, the man she was on a date with shattered all her expectations. Instead of being a perfect gentleman, the guy got so mad that he couldn’t park his car that he simply drove off and left her behind! In his defense, he was probably embarrassed that he couldn’t do a simple parallel park.

Surprises aren’t always a good thing!

Feelings are complicated. Sometimes, it’s kind of hard to tell if the person you’re into feels the same about you. And sometimes, we can be so clueless that, even if someone flat out asks us out on a date, we still feel insecure about whether they actually like us.

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Jenna wasn’t sure if she had been asked on a date, so she did not prepare for a date at all. Instead, she thought that the guy was inviting her out as a friend to watch a football game. It turns out he was asking her on a date, and she didn’t realize. She ended up wearing the wrong attire and painting her face — like any sports fan would do. We can only imagine the embarrassment when she got to the restaurant!