40+ Absurd, Awkward, And Embarrassing First Date Stories Jimmy Fallon’s Audience Shared Online

By Liezel L

First dates aren’t easy. In fact, they can be pretty nerve-wracking. It’s often your first — or only — chance to make an impression on someone you’d potentially want to spend years of your life with. And if you really like that person, you’d practically do everything to make them like you. Most people would shower longer than usual, fuss over what to wear, and put on their sweetest smiles while still trying not to lay it on too thick. No matter how much preparation you do, both with your own presentation and internet-stalking your date, there are still some things that can go wrong. Sure, they’re uncomfortable at the time, but, as Jimmy Fallon’s audience showed, bad dates can turn into hilarious stories. They’re like rom-com movies gone bad in real life. Here are some of our favorite #worstfirstdate replies.

It Was An Accident

We don’t like it, but looks do matter. Sadly, for this guy, he got into a small accident right before he got to his date’s house. Of course, when you’re in his situation, you have to tell the truth, right?

image courtesy of Jimmy Fallon/ Twitter

His circumstance is like one straight out of a movie. Luckily for him, he had a decent and believable explanation of why it wasn’t pee. Things could have been worse. We’re sure he’s learned a lesson or two since then.

Honesty Is The Best Policy

Being honest on a date is one of the best things you can do for yourself…and the other person. That way, you’d both immediately know the kind of person you’re dealing with, right? Sometimes though, it’s better not to be too honest. 

image courtesy of Jimmy Fallon/ Twitter

While this was the plain truth for Robert, we don’t recommend you be this brutally honest on your first dates. Luckily, though, things turned out for the best for him. Now, they have a great first-date story and a lesson to tell their kids.

Ouchie But Thanks?

Meeting someone who is smart or well-versed in topics you’re interested in can be intimidating but it’s also a great thing. Not only can you learn so much from them but you also have so much you can talk about.

image courtesy of Jimmy Fallon/ Twitter

This girl’s date wasn’t off to a great start when she realized she’d have to lead the conversation and we’re pretty sure she wasn’t having a ball when he straightforwardly told her that. There are better ways he could have said that. Or he could have just not said it at all.

That’s Why You Let Them Open The Door

Showing your date that you’re an independent woman is a great thing; there will be no questioning what type of person you are. Sadly, for Anna, her attempt at doing this ended her in probably one of the most embarrassing moments of the evening.

image courtesy of Jimmy Fallon/ Twitter

Luckily, the owner of the car wasn’t there. If they were, things would’ve gotten super awkward. Maybe next time, Anna should wait for her date to open the door or at least indicate which car it is to avoid getting the cops called on her.

Do Your Own Laundry

When someone keeps fidgeting in the middle of a date, it can be pretty distracting. That’s why, sometimes, it’s just better to take a break from the conversation and address the cause of the restlessness. Sadly for Marc, it wasn’t so simple.

image courtesy of Jimmy Fallon/ Twitter

Oh, no, no. It wasn’t a rat or a cockroach, which maybe would have been easier to excuse, but it was a pair of his mom’s undies. Calling that awkward is an understatement. Now, we wonder what other tricks he has up his sleeve…er sweater.

Double Check Names Before Clicking Send

When a date doesn’t go out as planned, a lot of us would want to talk it out or rant with our friends. When doing that though, it’s better to wait after the actual date, or what happened to this guy could happen to you. 

image courtesy of Jimmy Fallon/ Twitter

He really should have been more careful and just waited to text until after the date. If we were him, we would have just melted into our car seats. We feel so bad for the girl though. That’s harsher than getting ghosted.

Adorable Wingmen

Today, you can get lost trying to find your date’s address. But, you won’t have any problems since you can just call them. Before people had cellphones, though, it was pretty easy to get lost. You might even end up in the wrong house like this guy.

image courtesy of Jimmy Fallon/ Twitter

Thankfully for Todd, the house he ended up in became his saving grace. The old couple who lived in the home were so helpful in getting that young man back to his date. They were definitely his heroes for the night.

That Is True Love

Maureen’s story with her husband is the kind of tale we live for! It warms our hearts, and it definitely makes us believe that, yes, there is true love. Although, of course, not everyone’s soulmate makes the best first impressions.

image courtesy of Jimmy Fallon/ Twitter

For some, that may have been a disgusting occurrence. But what better way to get to know someone than to see them in all their glory including their embarrassing moments, right? As it seems, they really met their match on that date.

Better Sooner Than Later

Dating your relative is just a huge no-no. Nobody wants to be the butt of Game of Thrones jokes, right? Fortunately for this person, they managed to avoid that scenario before it got too late. Thank goodness for that barbecue!

image courtesy of Jimmy Fallon/ Twitter

Lesson learned: make some effort to get to know your family better! This will save you from getting into the same bed as someone you’re related to. Still, though, we can’t imagine how awkward it must have been for everyone at the event.

Caught Twice

Getting a ticket sucks. Not only does it stress you out, but the cop can also confiscate your license, which can take more of your time and get you in an even deeper hole than you were in. But you know what sucks more? Getting set up with the cop who gave you the ticket.

image courtesy of Jimmy Fallon/ Twitter

Linda already wasn’t having the best day of her life when she got that traffic ticket, but guess who showed right up to the blind date her friend set her up on? The cop who gave it to her. What are the chances? We hope she didn’t take it too personally.

This Is A Real Blind Date

Most people don’t trust blind dates, and understandably so. You won’t have a clue if you’re going on a date with a complete psychopath or someone who wants to murder you. However, this guy’s date was a lot more mysterious than most.

image courtesy of Jimmy Fallon/ Twitter

First of all, did he not have at least one picture to make sure he sat down with the right girl? And shouldn’t he have already been suspicious when she absolutely refused to communicate with him throughout dinner? Oh, we have so many questions with this one.

Salad Breath, Anyone?

Ranch dressing is tasty on a lot of things. It’s great on chicken wings, Caesar salads, french fries, and so much more. Do you know what it doesn’t pair well with? Kisses. Once it starts going with kisses, that’s when it turns gross.

image courtesy of Jimmy Fallon/ Twitter

We don’t know if Bennett’s date just really doesn’t know kissing etiquette — or eating etiquette, for that matter — but we’re guessing he didn’t grant her that kiss. She could have at least swallowed first before asking for one.

Isn’t That What Kids Do?

When this guy said he was clueless on his date, he wasn’t lying. Seriously, Mario Kart and crackers? Most people would spend hours wracking their brain thinking up what to do to impress their date on the first date, and you serve crackers and play Mario Kart?

image courtesy of Jimmy Fallon/ Twitter

That’s something that only kids, and maybe some teenage boys, would do. That poor girl must have been hungry and more than a little annoyed after that. Hopefully, Jimmy has learned from his mistakes and is now treating his wife to better dates.

That’s Worse Than Mario Kart And Crackers

Going to Taco Bell might not be a lot of people’s ideal setting for their first date, but the place isn’t actually that bad. The burritos are great, and the tortillas are yummy. What’s not great though is if you take your date there and leave her.

image courtesy of Jimmy Fallon/ Twitter

What Margaret’s date did to her was just downright rude. First, he was cheap about it, and then second, he ditched her. We also think he probably didn’t give her a proper thanks for it. He definitely wasn’t worth her time.

So Many Red Flags

Not everyone who’s spent time in prison is bad. Sometimes bad circumstances will result in time spent behind bars. In fact, plenty of people with criminal records are decent and are good partners. We don’t think the person Heather met would be the man for her.

image courtesy of Jimmy Fallon/ Twitter

For one, maybe he should’ve vigorously brushed his teeth and gargled with a lot of mouthwash. Or perhaps he could have withheld bringing his ex into the date conversation. Either way, it doesn’t seem like he would be getting any second dates.

Gambled On That First Date

Gambling can wreak havoc on someone’s finances, and it can also mess with someone’s personal life, including their dating status. This woman’s date, for instance, not only had her paying for the date, but we bet she left a little disappointed.

image courtesy of Jimmy Fallon/ Twitter

It’s unfortunate that he lost all his money gambling, but it’s not something you can support. We hope he had a revelation about his gambling problem and found some help for it. Who knows? Once he gets rid of it, maybe his chances in the dating pool will improve.

Double The Trouble

When it comes to dating, there are chances that the person you’re going on a date with is possibly talking or interested in other people too. Sadly for Kelsey, that fact was rubbed in her face when her date decided to squeeze in their first date with another girl.

image courtesy of Jimmy Fallon/ Twitter

That was a horrible thing to do, and he deserves to be knocked down a peg. Thankfully, the waiter had Kelsey’s back and told her what was going on. That was a lifesaving moment. If Kelsey didn’t know, who knows what kind of world of heartache she’d be in.

Through Thick And Thin

Usually, when health complications arise when you have a date planned, you’d want to cancel and maybe reschedule. This woman, however, still decided to push through, despite her ulcer and subsequent side effects from her medication. She was lucky with her date, though.

image courtesy of Jimmy Fallon/ Twitter

Farting and burping don’t usually make a person look appealing to everybody, but it seems those just did the trick for Ashley. Maybe it was showing that she’s human and not some perfect girl, her date saw his future soul mate in his date.

Garlic Protection

In fiction, people used garlic to protect themselves against creatures like vampires. However, this girl was using garlic as a protection against something else — a kiss on her first date. Now, we get not wanting to be intimate on the first date, but really? Garlic?

image courtesy of Jimmy Fallon/ Twitter

As it seems, this girl had something against being kissed on her first date. She didn’t even seem to mind the garlic breath she’d have the whole day. Still, she could have just said it. She didn’t have to go through all that garlic fest.

Daddy’s On The Guard

You can’t date someone and have your parent there at the same time. No. That’s just against the unspoken rules of dating. Everyone knows that. Dates are supposed to be just about the two of you. Parents are for later.

image courtesy of Jimmy Fallon/ Twitter

That didn’t stop this girl from having her dad in the picture — or maybe it was the dad who didn’t want to be left behind. Either way, we don’t think poor Will got a second date after meeting the dad way too early. But hey, who knows? Maybe the two got along great.

Date Trip To The ER

Most people would imagine that stubbing a toe wouldn’t cause that much of a problem. Of course, it will be painful, but it’s not something many people would cry over. Sadly for Alida, it was problematic enough to end up in a trip to the ER.

image courtesy of Jimmy Fallon/ Twitter

While a broken toe and a ton of stitches are terrible, the evening wasn’t entirely ruined. She may have been unlucky with the injury, but her date went well enough for a second go. Even if the first one had to be cut short, she got to go on a real date later.

Nope, Not Tom

What’s worse than getting ghosted or dumped? Well, a lot of things, actually, but possibly the worst is your date calling you by the wrong name. To be precise, the name of their next date! That just hurts on another level.

image courtesy of Jimmy Fallon/ Twitter

It was already awkward to have 10 of her friends there when he was only expecting to pick her up. But having her blackout wasted and her introducing him by another guy’s name? That’s the cherry on top. We’re pretty sure there wasn’t a second date. 

Not The Time For Pranks

First dates are usually for the pleasantries, the nice things, the shy things, and the proper things. People don’t usually start pulling out the pranks there. This woman’s date seemed to think otherwise, and we don’t think ended well for him. 

image courtesy of Jimmy Fallon/ Twitter

We’re assuming it was a prank, because we can’t think of any decent explanation for his behavior. Saying something smells off and then shoving it in someone’s face is what best friends do, not people you’ve just met! Someone needs to teach him some manners.

Undisclosed LGBTQ+

Most people would hope that their dates won’t have any interruptions or confrontations, but that wasn’t the case for Michelle on her first date with a new guy. If we were in her position, we’d be pretty darned confused, and we’d want a good explanation.

image courtesy of Jimmy Fallon/ Twitter

The waiter overstepped boundaries and was unprofessional. Plus, it was presumptive of him to assume the guy was gay rather than bisexual, which is already a problem. Still, it must have been more than a little awkward for Michelle to be in the middle of that situation.

The Family Date

Usually, you’d expect to meet your date’s parents when you’re getting serious or a couple of months into the relationship, not during your first date. That’s just a big no-no of relationships and can be a huge dealbreaker for some — most? — people.

image courtesy of Jimmy Fallon/ Twitter

What Kelly’s date did was just too much. He’s a grown man and can do things alone, including going on a date. If he wanted to bring his parents along, he should have at least said something to Kelly before surprising her with a family outing. 

Scratch His Name Of Your Memory Girl

When you’re on a date, one of the things you shouldn’t do is borrow money. It’s embarrassing, and it doesn’t make a great impression of you as someone they’d want to be able to lead a stable life with, right? This girl’s date did more than that.

image courtesy of Jimmy Fallon/ Twitter

Sure, he got lucky when he won that $60, but that’s where his luck ends. He even had the gall to invite his date to a strip club. We don’t think he was serious with that date, so in the end, Chelsea is the one who really won.

Rollin’ Out The Facts

When you’re not familiar with something, especially at a restaurant, it’s often better to ask for clarification rather than make an embarrassing mistake. Unfortunately for this lady, she didn’t do that and ended up ordering a buffet on her first date. 

image courtesy of Jimmy Fallon/ Twitter

Her date must have been wide-eyed when the waiter laid down all the food she ordered. But hey, if you’re both foodies, this could actually be a funny mistake that could have gone down quite well. At least now she knows more about sushi.

Tinder And Wedding Dresses

Some people might be skeptical of Tinder, but hey, don’t knock it until you try it. Dating apps can be a pretty great place to meet all sorts of people. You can even make new friends there if the romantic thing doesn’t work out. Sadly, that’s not what happened to Claire.

image courtesy of Jimmy Fallon/ Twitter

Her entire night must have been wild. Just imagine going in for a date and picking the guy’s ex’s wedding dress. We really want to know what happened in the journey in between because that’s a huge leap to wrap our heads around.

Enough Said

Many things can go wrong on a date — bad food, lame jokes, stale and stilted conversations, and even wardrobe malfunctions. And while some people might think that would be the worst, those pale in comparison to what happened with Jon.

image courtesy of Jimmy Fallon/ Twitter

Five words. That’s all it took for us to realize just how badly he messed up on that date. There’s nothing much else to say; all we can do is cringe in silence. Hopefully, he brought her to the hospital and that she was okay.

Not His Ideal Girl

The evening itself might be the hardest part of it all but finding who you’re going out with isn’t necessarily easier. There are millions of people out there, and you have to find someone who fits into your ideals. Sometimes, you just have to take a risk.

image courtesy of Jimmy Fallon/ Twitter

We can confidently say that not everything this guy Tweeted happened on his date, but if even half of it is true, it wasn’t a memorable date, to be sure. She wasn’t his type, had different tastes, and was downright rude.

Elbowed Into Love

If the person you went out with elbowed you in the face, would you give them a second chance? Many people might think twice about it, but Mike’s wife decided to give him that chance, and well, it seems like the pain was worth it.

image courtesy of Jimmy Fallon/ Twitter

Sometimes, all people need is a little nudge to the right person, although we don’t recommend pushing hard enough to cause an injury. Seriously though, their story is adorable. It’s the story we only see in rom-com movies. If only everyone in could end up happily together like them.

Do I Know You?

When going on first dates, it’s usually not recommended for people to drink too much beforehand because once you’ve crossed that line from tipsy to drunk, so many things can go wrong. Don’t believe us? Just take a look at Thomas right here.

If we were his date, we would have been uncomfortable and downright offended. Just for some fun, though, we’d reign in the annoyance, go with it, and see how long it would take for it to click. Hopefully, it didn’t end up too badly for her.

He Found Her Too Adorable

It’s not wrong to try to be cute on dates, but usually, when people try to be cute, especially on first dates, there’s still a boundary that they respect. For Danielle, her date might not have overstepped and went from charming to weird. 

image courtesy of Jimmy Fallon/ Twitter

Kissing someone on the nose might be a cute thing and even a sweet gesture, but we wouldn’t recommend blowing on anyone’s nose. That kind of thing seems to be something for more serious relationships. Maybe he had a few too many drinks, like the previous guy.

Life Changer

Sometimes it’s nice to hear people say, “You helped me make this decision,” especially if it’s for a good cause or for bettering themselves. In this case, though, we don’t think helping his date make a big life decision was a big compliment to this guy. 

image courtesy of Jimmy Fallon/ Twitter

She might not have intended for it to hurt but let’s face it, it stung. Did she just not like Rick enough? Did he do something wrong on the date? Was she turned off from men because of him? We hope he recovered his self-confidence after that. 

Not That Kind Of Date

More often than not, it’s great to know the details of the date, so you know exactly what to do. It’ll help you pick out what to wear, what activity you’ll do, etc. And don’t assume you know the plan, either. Otherwise, you could walk into the wrong type of “date.”

image courtesy of Jimmy Fallon/ Twitter

We commend her enthusiasm and commitment to attending a sporting event, but a little clarity on the date’s part would have been helpful. If her date was a real keeper, we think he still would have invited her to their table like nothing’s wrong.


Setting up another person with someone else is not always a good thing. Not only is it uncomfortable, but it’s not a surprise that can easily be dealt with. In Seth’s case, he only knew that he got set up with a different person right when he arrived at their doorstep. 

image courtesy of Jimmy Fallon/ Twitter

It must have been awkward for him. And who wants to break an old woman’s heart, right? If it were us, we’d probably take her out to her favorite spots in the city and make sure she has a nice time, but we’d be honest with her.

Great Tactic!

When you’re in the movie theater, there are times when you can’t avoid getting seated next to people you don’t want to be near. They can be loud popcorn chewers, their conversations might be too loud, or maybe you’re just really uncomfortable next to them. 

image courtesy of Jimmy Fallon/ Twitter

This girl decided that she didn’t want to endure that kind of torture on her night out with her friend, so she did something that completely stunned them into silence. And, well, it worked. It must have been a few awkward moments of silence, but it was worth it.

How Rude!

Comments that start with “I thought you’d be…” don’t generally go over well on dates unless you’re a clever person who can back up whatever you’re going to say with a valid explanation that won’t bruise their confidence and ego. This guy was not one of those people.

Nope. He was just plain rude. Sure, sometimes you have to be direct with your date, but even then you need to be polite and watch your words. What Catherine did was definitely justifiable in the face of that kind of behavior.

When Your Brain Just Stops Working

People who can keep their wits about them and their thoughts straight when they’re finally on a date with someone they really like are admirable. Usually, many people would be nervous, having their tongues tied and their brains stop working properly. 

image courtesy of Jimmy Fallon/ Twitter

It’s okay, Jordan. We get you in this one. The butterflies can just turn our brains to mush sometimes. Hopefully, he found it silly enough to just laugh it off. A good sense of humor is hard to find, so he should have taken this as a sign for a second date.

Over Here!

Some people aren’t great with names, and others aren’t good with faces. For the latter, it would take more than a picture or one meeting to remember what someone looks like. One date might not be enough to commit someone’s face to memory. 

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It was funny how he let her walk around for a few minutes first. It’s also quite a story to tell their kids. It’s just adorable, especially because they ended up together. To be honest, this is more hilarious than it is cringy for a first date.

They’re Watching From Everywhere

With technology around us at all times, we’re becoming more aware of cyber threats. Some of us stick paper over our laptop cameras, but others take it a little further. They go all out and cover their phones, fearing that they’re under surveillance at all times.

image courtesy of Jimmy Fallon/ Twitter

While there is some truth in it, such as when we get personalized ads, the “government is watching” theory can be neither confirmed nor denied. We admit it’s a great conversation starter, but he handled the situation could have been a lot better.

Don’t Mind The Passenger

Dating while you’re on the job or doing a little overtime isn’t recommended. Of course, there are ways to make it work…unless you’re a funeral director with a body in the back of your car. That just seems like a scene straight out of a horror movie. 

image courtesy of Jimmy Fallon/ Twitter

There’s nothing wrong with being a funeral director, but really, he could have just messaged her and told her he would be running late rather than taking her along. Dead bodies don’t make the best first impressions for a new relationship. 

Forever Mama’s Boy

As adults, there are still things we’d need to ask our parent’s permission for, like selling their house, having someone live in their home, or even getting married. What that doesn’t include is watching films rated for younger viewing audiences.

image courtesy of Jimmy Fallon/ Twitter

We’re sorry to say, but she dodged a bullet there. If he was still asking permission to watch R-rated movies, we wonder what else he’d be asking his mom permission for if they ever got into a long-term relationship. No, thank you.

Tricked Into The Perfect Date

Here is one that we are sure will warm your hearts. After being on the dating scene for a while and experiencing the ruthless atrocities of the streets, it’s totally understandable when one decides to take a break. It’s actually recommended.

image courtesy of OctopussSevenTwo/Imgur

That’s exactly what this girl had decided to do here until a man he was talking to decided he would turn the tables on her. But in a good way. We can’t even get mad at the guy’s game because that was super smooth!

That’s Harsh Buddy

When you’re in high school, everything can seem a little bit brighter, a little bit more hopeful, and a little bit more romantic. Sadly, there will always be one thing that will break those rose-colored glasses to welcome you into reality. 

image courtesy of Jimmy Fallon/ Twitter

For Kyle, one of those moments might have been this first date. He might have spent hours mustering up that courage, and hey, he even asked permission. So that kind of rejection just hurt. At least now he’ll know how to manage his expectations.

Boy Not Worth It

It takes some people a whole date, a few weeks, or even a full relationship before they see some red flags with their significant other. However, Leslie didn’t have to wait too long before she saw why her date might not have been worth it. 

image courtesy of Jimmy Fallon/ Twitter

Just because he failed to parallel park 3 times doesn’t mean he gets the pass to just leave her hanging there. Who does that? That is not cool! He could have at least apologized or maybe messaged her the next day. Judging by what he did, there’s a big chance he didn’t.