40 ‘Worst First Date’ Stories That Made Jimmy Fallon Laugh Out Loud

First dates can be exciting, but things don’t always go as planned. Late-night talk show host Jimmy Fallon took to Twitter to ask his followers to share their #WorstFirstDate experiences, and the results are both cringe-worthy and hilarious.  It’s always entertaining to hear about other people’s misadventures in the dating world. So sit back, relax, and get ready to laugh (or cringe) at these epic first-date fails.

The real challenge was explaining the spill to his date without it being misinterpreted. Fortunately, Patrick was able to save face by clarifying the situation.

We’d like to think that they were able to have a laugh about the whole situation and that funny story is one they can tell their kids one day. But maybe that’s just wishful thinking.

We’re not sure how we would react if we were in Mojo’s shoes. It’s a sweet gesture, but also a little strange. If your date has to ask for permission to do things, maybe it’s time to reevaluate if they’re ready for the dating scene.

We certainly can’t remember a time that a grown man had to ask his mom’s permission to see a Rated R movie. We can confidently say this wasn’t the start of a blooming love story.

It’s never fun when you run into an ex or when you run into your date’s ex, especially when you’re on a date.

Here’s a pro tip: when it comes to other people’s relationships, it’s always best to mind your own business. Plus, if you’re going to have a confrontation, it’s probably not the best idea to do it while someone is trying to enjoy a romantic evening.

While it’s sweet that Kelly’s date enjoys his parents’ company, it’s also important for people to have some independence – especially at 25 years old.

But hey, at least Kelly’s date has a strong bond with his family. And it looks like his mom got some great leftovers to take home and enjoy another time. Best of luck to him finding someone that is just as close with their own family. 

Good thing Christine had the patience to stick it out, because we would have been running for the hills. It’s like something straight out of a horror movie.

If he’s comfortable enough to do something like this on the first date, we can’t help but wonder what other quirks he might have.

And if that wasn’t bad enough, he even left her to go buy a scratch-off ticket on his own. But luck was on his side when he won $60 (even though he probably didn’t deserve it). 

When we think of first date stops, this isn’t exactly the first place that jumps to our minds. This guy clearly didn’t have a taste for romance.

But even with a bleeding toe and ten stitches, they managed to charm their way into a second date. Accidents happen, but sometimes they lead to unexpected silver linings. Just goes to show that a little bit of perseverance can go a long way.

But she managed to swing a second date. And, if she was able to still find the mean interesting while she had to get stitches then it must be a real connection. Maybe this bad first date led to a pretty fantastic second date.

We bet her date was pretty full after all that sushi. But hey, we think food is always a great idea for a date. Plus, now she knows to be more specific when ordering her favorite rolls in the future.

At the end of the day, the whole sushi fiasco could have made for a funny story to talk about on their second and third dates. Hopefully, those ones have a reasonable amount of food.

It’s also a good idea to avoid strong-smelling foods like onions and garlic. Trust us, no one wants an unpleasant make-out session! But, this woman clearly had other plans in mind.

You sure can’t say she isn’t direct. You have to set your boundaries early, but this was a pretty interesting way to do it. Better luck next time, Ben!

This is not only rude and disrespectful, but it’s also a major red flag and a surefire way to ruin the date. So, remember to always be respectful and considerate of your partner’s feelings, and you’ll have a much more enjoyable time together.

However, we can be fairly certain that this pair won’t be making it to the altar. Sometimes, one is more than enough when it comes to dates.

Chris must have been feeling pretty mortified. And to make matters worse, his date had a whole group of friends over when he wanted to take her out. That must have made things super awkward.

To be honest, we think Chris probably dodged a bullet. And who’s to say that Tom and this woman didn’t hit it off? Just because this wasn’t a budding love story for Chris, it doesn’t mean it wasn’t just that for good old Tom.

Robert was pretty upfront out the gate with this woman who would later become his wife. I suppose he was charming enough that she was willing to overlook the little thoughtless comment and now they have 3 years of marriage to show for it!

Robert and his wife might look back on their first date and laugh about it. We must assume that they have had plenty of lovely dates since which have made up for the lackluster first impression.

And it’s even more difficult to enjoy yourself when you are being insulted on top of it all! Unfortunately, this girl’s date ended up making a remark that came off as him assuming she was not intelligent. Definitely a red flag!

Either way, it sounds like he lost out on a golden opportunity to date a very intelligent woman. His loss!

Despite the mix-up, the date ended up being a success and the two are now happily married. It just goes to show that even the most seemingly embarrassing moments can end up being a funny memory to look back on.

This is one of those rare instances that a bad first date doesn’t mean the demise of a relationship. Rather, it ended in a marriage and a silly story they can share with their kids in the future!

Luckily, the car’s owner wasn’t around, so there was no awkward confrontation. Next time, Anna ought to ask her date what their car looks like to avoid any mix-ups. Being a little extra cautious can go a long way in preventing embarrassing situations.

Plus, running away from your date for any reason isn’t typically a very encouraging start to a romance. Better safe than sorry.

It looks like Will and his date might not have gone out again after this little cinema mishap. Poor Will was introduced to the parent way too soon in their relationship. He might be a little bit hesitant about going to the movies with a potential love interest now. Can’t say we blame him!

Either way, it must have been a pretty tense date and we don’t image there was a follow-up after that. We can only hope that these were highschoolers and not grown adults because that would make the whole thing even more strange!

But sometimes the strangest dates end up being the best ones. Even if she didn’t happen to met her soulmate that night, she got a story she’ll certainly never forget. 

It’s hard to imagine how the first half of the date even went. We imagine it couldn’t have been as eventful as the second half. One thing’s for sure, at least Claire can add this wild Tinder tale to her collection of funny stories to tell her friends.

Although, we are curious to know how this ended up happening. And is the woman okay? No one expects to go home with hospital bills instead of a good night kiss.

Did they end up together or was it a complete disaster? One thing’s for sure, we hope his date is okay. Accidents happen, but we can’t help but wonder what led to this one. We wish Jon had filled in the missing details for us. Regardless, we hope everything turned out alright in the end.

On the bright side, at least this person found out before things got too awkward. We can all agree that finding out your date is a relative is definitely one of the weirdest things that can happen on a date.

I mean really, what are the odds of something like this happening in a world filled with billions of people? All we can do is feel lucky it didn’t happen to us!

No, it wasn’t an animal. It was a pair of his mom’s panties! We can’t decide whether to laugh or be amazed at Marc’s magician-like skills. We wonder what other tricks he has up his sleeve (or sweater).

See, Todd accidentally entered the wrong house, but it turned out to be a blessing in disguise. Can you imagine trying to navigate through life without our beloved cell phones? Back in the day, it was so hard to get in touch with people. But thank goodness for technology and the gracious couple who helped Todd out!

To avoid any awkward moments like this, it might be best to put the phone away while on a date. Trust us, it’s not worth the embarrassment. Even if you do make a mistake, it’s best to just wait until after the date to share the mishap with your friends.

Despite having an upset stomach on her first date, she and the guy ended up getting married and spending the rest of their lives together. Now that’s a happily ever after! So don’t let a little stomachache get in the way of finding love. Embrace the unexpected and who knows, you may just end up with your own fairytale ending.

Kelsey had a helpful ally in this situation – the waiter. This observant server had probably seen all sorts of dating drama and was happy to give Kelsey the scoop. As it turns out, Kelsey’s date was actually seeing two people at the same time.

While honesty can be important, it’s also important to be mindful of how you say things. Catherine handled the situation like a pro and gave her date a taste of his own medicine by dumping a drink on his lap. Sometimes, a little bit of instant karma can go a long way!

Imagine Linda’s surprise when she later learned that her ticket-giving cop was also her date for the evening! A small world indeed. Here’s hoping that he was able to show a little bit of chivalry and revoke the ticket. After all, everyone deserves a break every now and then.

But hey, sometimes people just get caught up in the excitement of gambling and lose track of their limits. It’s never a good idea to support someone’s destructive behavior, but sometimes you just have to do what you can to get through a tricky situation. Here’s hoping Heather’s date can learn to gamble responsibly and not put himself or others in such difficult positions in the future.

Plus, if you’re not even eating dinner on a date, it can make things feel really awkward. If we were in Collin’s shoes, we’d be extra careful about who we went on dates with in the future, or at least make sure to get to know them a little better beforehand.

Despite the girl’s silence and lack of communication during dinner, Scott never suspected a thing. We can’t help but wonder how he didn’t notice that she looked different from her picture. This mysterious date has us full of questions!

Despite the initial awkwardness, Mike’s wife stuck by his side and showed herself to be a true keeper. It’s important to remember that a little nervousness is natural when it comes to romantic moments, but with a little patience and understanding, anything is possible.

During their first date, her partner treated her poorly and ended up ditching her at the restaurant. How rude! Margaret deserves someone who will treat her with respect and not try to skimp out on the bill. This guy certainly wasn’t worth her time or energy.

But hey, it’s all part of the learning experience. Kyle’s ex may have turned down his affections, but she taught him a valuable lesson about love and relationships that he’ll carry with him for the rest of his life. Even at a young age, it’s important to manage our expectations and not take things too seriously.

We can’t say for sure what happened before this moment, but it seems like things were going okay until this point. It’s always a good idea to be mindful of your actions on a date and make sure you’re not making any weird moves. Just stick to kissing the nose and you should be good to go!

Before puckering up, it’s always a good idea to make sure you’ve fully swallowed your grub. Unless, of course, you’re a bird or something. After this ranchy incident, Bennet called it a night on this date.

But things took a turn for the worse when Thomas stumbled into the bathroom. He ended up mistaking his date for someone else and asked her out again! We can only imagine how awkward that must have been for her. But hey, at least it’s a story to tell for years to come! Just try to remember to pace yourself on those drinks next time, Thomas.

We’re not sure what we would have done in his shoes, but maybe just treating the grandma to some ice cream would have been the best approach. It’s definitely a strange lesson in the importance of double-checking details before heading out on a date.

While it’s understandable to be concerned about privacy, it might also be a good opportunity to learn more about internet security and how to protect oneself from hacks. On the other hand, placing the phone face down on the table might have seemed a little suspicious. Maybe Klara’s date should have just brought out their phone instead.

We’ve all had those moments where we wish we had a pack of mints or gum on hand to freshen up. But it’s important to remember that good oral hygiene isn’t just a nice-to-have – it’s a must. Next time, maybe this guy will remember to brush and floss before heading out on a date.

But let’s be real, who hasn’t had an embarrassing moment like that? And if your partner can still love you even when you’re at your grossest, well, they must be a keeper. These two are a match made in heaven, and their story just goes to show that love can be found in the most unexpected of places.

Despite being a little nervous, Jordan’s quirky personality came through when she joked about how she was breathing in response to the compliment. All in all, it sounds like this worst date could have been much worse.