Top 40: The Funniest First Date Disasters Real People Shared with Jimmy Fallon

A first date can be anxiety-inducing, particularly if you're meeting somebody you really like. You spend far longer looking in the mirror than you normally would, bust out your fanciest fragrance, and wear a winning smile to match your carefully selected outfit. Despite all this work, things can go rapidly wrong, sending your night into a tailspin that’s horrific for you but hilarious for everyone who hears the sorry tale.

A bored Jimmy Fallon came up with the adorable idea of asking people to send in their #WorstDate stories, complete with all the juicy details on how they handled the circumstances. These absurd and extraordinary date stories will leave you in a fit of giggles. Best of all, you’ll feel a whole lot better about your own dating fails! 

We understand why they ran, but we imagine the old couple was just delighted to have some company for once. We hope both sets of people still enjoyed a lovely night after their strange encounter with each other!

There's a ton of subtleties missing here, but the finale of the story is clear. There’s little else to say other than that we hope the poor woman is okay! 

He dated a complete stranger and didn’t realize his error until she’d already scored a free meal out of him. What a peculiar development! We have so many questions about the mystery lady.

If we were in his situation, we'd most likely take the grandma out for frozen yogurt or something. Though it’s an unusual circumstance to be in, that doesn’t mean you can’t show a bit of kindness and good humor.

Helene’s rejected date tried to break into her apartment to “make sure she was fine.” She certainly wasn’t fine after that! Lesson learned: develop your excuse-making skills, especially if you think you might have to call off a date at the last minute. 

Where it fell, however, is quite unfortunate in light of the fact that the stain would look mighty suspicious. Whether his date accepted his explanation or not is a detail we’ll probably never know.

It’s such an awful feeling when accidents like this occur. Apart from the obvious physical pain, there are always those thoughts of “why didn’t I pay more attention?” Accidents happen, so all you can really do is tough it out, just like Alida did.

In this case, the server took matters into her own hands. She leaned in and informed Kelsey that her date was a scheming individual who was dating two ladies at once, in the same restaurant, at the same time! It’s like a plotline out of a 90s romantic comedy.  

Needless to say, this adult temper tantrum does not have valid reasons at all. Nobody deserves to be disrespected in public. Whatever his issues are, this guy does not deserve a second date. His behavior is appalling. 

Who would’ve thought an ulcer could transform into an enduring memory and a beautiful love story? Despite her GI issues, this man still fell in love and married her. What a sweet conclusion to an otherwise embarrassing story. 

This poor woman had her face thrust into a dish after her date requested that she sniff it. This is such poor form and would be a dealbreaker for most people. It's one thing to request that your date smell your food; it's another to push their nose right into it. 

He got fortunate when he won $60. However, instead of splitting the winnings with his date, he dropped her home so he could enjoy his cash. In the end, Chelsea was the real winner as she didn’t have to waste a single extra second on this fool. 

Ben's date didn't appear to have any desire to plant a kiss on him. Indeed, she took measures to ensure that it definitely wouldn’t happen. The girl courageously dispersed garlic powder on her pizza, and just in case he wasn’t sure about her motives, she spoke up and made it abundantly clear. 

Here’s a piece of advice for everyone considering a surprise date: don’t tell the person you want to date that you’re going to a sporting event if you really have a fancy dinner planned. In fact, we’re not so sure surprise dates are a good idea at all. Why not just come out and say that you’d like to go on a date? 

How do you feel about this? Would you consider a ranch-filled kiss? We’ve discussed the matter and come to the conclusion that if a mouthful of half-chewed food were involved, we’d gag. However, if it’s just ranch, maybe that wouldn’t be so bad? A mouthful of chocolate fudge would be better, though! 

Imagine getting excited to meet your blind date, and when that big moment arrives, it turns out to be your landlord. If that’s not awkward enough, you’re one month behind on rent! We wonder how long that date lasted.

As it turns out, the poor kid had a pair of his mother's panties stuck in his sweater. How embarrassing! We would either burst out laughing or shrink in horror if this happened to us. Hopefully, he had some better tricks up his sleeve to save the date. Poor Marc!

He took her to Taco Bell for their first date, which isn’t so bad. Admitting that you want to save money is okay too. However, ditching your date after you’ve had your fill is one step over the line. 

The fact that a young woman decided she never needed to date anyone again after one date with Rick could be taken as a form of criticism. However, we prefer to see it as a beautiful thing that he helped this woman have certainty about a momentous life decision. 

Who does such selfish things? Unfortunately, it took him two dates with this woman before he realized it was a pattern – and not one he wanted to have in his life. Good luck on your next date, Mack!

This is straight-up peculiar, and we would be dumbfounded if we found ourselves in her position. We can only hope that there’s a person out there who would find this kind of behavior endearing rather than off-putting! 

At least this dismal date provides a lesson for everyone: take care of your teeth! Talking about your ex on a first date may be a mood killer. Add rotten teeth to the mix, and you have a definite dealbreaker.

Though it sounds like Michelle’s date may have been covering something up, it was also pretty inappropriate for this waiter to step in. It seems there may have been some personal motives at play.

Her date must've been full from all the sushi she requested. We wouldn't look at this as a horrendous date since sushi is so delicious and easy to pack up and take home. We hope they took the excess home as a tasty souvenir of this hilarious date.

It's lamentable that Heather needed to pay for the date since he had lost all his cash gambling. Sadly, Heather was left with no other choice. However, we doubt this gambling fiend earned a second date. 

This is not cool and so ungentlemanly! If we were in her shoes, we would expect a giant bouquet of roses with a note apologizing for this unbelievably rude behavior. At the very least, we hope he got some driving lessons to brush up on his skills. 

Things got ugly when Linda discovered her date was the cop who had given her the ticket. What are the odds? We wonder if he had the option to cancel the ticket and possibly let this one slide.

We understand that certain individuals are obsessive about their vehicles, but this one is just too much to handle. We do give him full points for his honesty, though. He just showed his true nature to Jennifer, so she had the opportunity to leave if it wasn’t for her. 

We feel terrible for both this woman and her date. We’ve all accidentally sent messages to the wrong person before, but in this case, the consequences were brutal. At least it happened on the car ride home so they didn’t have to endure too much more time in each other’s company!

When she went on a date to the cinema, two random guys chose to join her and her date. She wasn't okay with how close they were sitting so cleverly implied that the two must be dating if they were joining Marie and her beau for a double date. Checkmate!

This young lady put forth a valiant effort, and her date finally admitted that it wasn’t shyness that made him hesitant to talk. He came with the expectation that she would have been unintelligent. Do you think an assumption like this is a red flag? Or could he be forgiven?

She did not drool because her date was hot but because the anesthesia didn’t wear off in time. Her self-declared #worstfirstdate was indeed terrible, but it was all worth it. They’re now married, and we’re sure this awkward moment makes a wonderful story whenever curious acquaintances ask how they met. 

This really would be a bizarre and unpleasant experience for the average person. There’s nothing wrong with being a funeral director. However, you might want to at least give your date some warning before introducing them to one of your “clients.”

Though the moment described would’ve been awkward, it is kind of cute. If we were in this situation, we'd go with it and see how long it took for him to realize what he was doing. At least she knows he’s genuinely attracted to her. We bet some of the other ladies on this list would happily swap their experiences for this one! 

From the vibe of the post, we doubt there was a subsequent date. Apart from the fact that Will met the dad far too soon, it would’ve been so freaky having him staring at them throughout the date. We're certain he's now far more careful about bringing dates to cinemas.

This story takes the cake for being the most awful date. It may be gross to date somebody who farts and burps constantly, but we’d much rather that scenario than this one! That would’ve been one awkward family BBQ. 

The super-curious mom went above and beyond to make sure her daughter didn’t make any awkward mistakes. Here’s hoping Daniel made sure that his date/cousin was okay after this shocking discovery.

Once in a while, all you need is a little push to fall in love. However, that push should never come literally from an elbow to the face! It is nerve-wracking going in for the first kiss, and it seems Mike wasn't at all prepared for it.

We can envision this being something you might do as a joke with a partner you’ve been with for years. However, blowing someone’s nose like a trumpet is a mix of oddness and intimacy that just doesn’t work on a first date. 

When he attempted to kiss her, she took it as a joke. His move was a sweet one, but she just ignored it. On the bright side, this type of dismissal can help you learn to be more subtle in your approach as you get older.

It would seem that Kelly's date was simply hoping to bring his folks since he enjoys having them around. Be that as it may, at 25 years of age, he should be at least a little bit more independent. 

Catherine's date clearly didn’t get the memo. Of course, it’s perfectly fine to have your own preferences, and it’s important to be honest with people. However, there are tactful ways to discuss these things. Catherine responded in a hilariously forthright manner. Talk about instant karma!

Collin's girl didn't appear to be keen on the date by any means. If we were Collin, we'd improve our pre-date screening processes. Of course, it’s a little late now, considering he’s been murdered and all. 

Remarkably, things turned out really well for Robert. Indeed, he found his better half. This is a story to tell their children, and perhaps they will all be able to giggle about it later on.

Needless to say, the guy was looking for someone to listen to his bragging skills and his country’s triumph. Poor Meredith must have learned a lesson or two from this terrible date.

Her date disclosed to her how great she smelt, and yet, she was so anxious she misunderstood him. Rather than accepting the compliment, she made a hilarious and adorable mistake. All things considered, this terrible date doesn't sound so awful. Compared to the other items on the list it’s a dream date! 

To make the situation worse, his date had 10 companions over, and they were all partying when he thought he would be taking her out. That’s 10 extra witnesses to his embarrassment. We can imagine his reaction.

While this may sound sickening, it was clearly a precursor to love for these two. What better approach to become more acquainted with somebody than to see them in their full and total wonder? Perhaps this onion tactic should be added as a tip to dating advice articles! 

Tip: don’t discuss the prospect of having children with someone on a first date. Unless you want to make them quickly disappear, with no chance of ever seeing them again. If you’re genuinely interested, take it slow!

Shawnda, who goes by the Twitter handle @shawndar, learned this lesson the hard way. She had forgotten to be the tooth fairy and was just getting the job done when her son woke up. Sorry, kiddo!

We should have known that anybody could have easy access to those secrets once they found the book. That is the story of @meesheee17 who wrote “Pay mall back” in her journal and was then caught by her mom. Once again, why are these mothers snooping in their kids’ journals? 

Everything seemed to go according to plan, but upon watching the news the next day, she realized with horror that she was in the background. Tough luck there, @lofome. Maybe next time, be on the lookout for news cameras.

That’s what @noteverygirl91 did. Instead of going on a date, she canceled it pretending she was sick. The problem was, her date was also at the Styx concert and could see her in the front row.

Twitter user @kaitlynmidgett took the gamble and got some ink. Unfortunately, her tattoo was revealed accidentally when she asked her mom to look at a weird bug bite.

There’s no doubt in our minds why he got a zero on that assignment – it was the score he deserved for cheating. Even if he’d gotten away with it at the time, this would have caught up with him. When you cheat, you rob yourself of learning opportunities, meaning you’re only cheating yourself. 

Twitter user @ZabumbaHI thought that she outsmarted her mom when she snuck out of the house. Unfortunately, her mom was able to find her diary and busted her. To be honest, we feel like the mom was the one in the wrong here for not respecting her daughter’s privacy. 

Oddly enough, she was writing out a speech from Independence Day. For what reason, we’ll probably never know. Her boss saw her and thought she was taking notes about the meeting. Now Michelle has to scramble to come up with something relevant to include in the minutes she was asked to write! 

Many are successful, but some are busted right at the doors. Twitter user @StillNotJenna tried to bring pepperoni and sausage using a tote bag but failed due to the strong food smell.

Failure was written all over her plan as her teacher decided to visit the library that day. Imagine deciding to skip class but then ending up precisely in the spot where your class is going to be taught! 

How would you even bounce back or apologize to the stranger that you just sniffed? I mean, come on Leyla. What’s wrong with a simple “hey, cuz”? Hopefully, this was a valuable lesson for her.

The plan was simple for @LisaTreon: Wrap the Christmas presents as neatly as possible and attach tags saying “From Santa.” However, her plan backfired when she forgot to turn off her PC as the kids saw her tags. Whoops! 

If you are going to hold a party, it is crucial to make sure that everything is clean. That was not the case with @McSweeneyPam as she was busted when her parents saw empty beer cans in the garage.

They were on their way home when they picked up the pizza. She gave him the box to hold in the back seat. Upon arriving at their house, the only thing left was the crust.

She was ten years old when an accident happened as she was playing on the playground. Although she acted quickly to hide her peed pants, it wasn’t any help at all. Hopefully, her friends still played with her that day.

This event happened in real life for @mattliptoncomic. We are not condoning underage drinking, but if he had a better cover story, he might have gotten away with it.

Twitter user @leapbaby625 shared a story about accidentally putting a hole in the wall. She covered it up with a calendar, and surprisingly, nobody noticed it. What a slick move there, Sara.

However, as @Meek_Milf discovered, lying is not a strong point for most moms. She tried to trick her 3yo by going to her room to fold the laundry. She went there to eat a piece of cake, but her toddler followed her and caught her in the act. Busted!

This young lady will always be remembered as the party starter by her classmates. Twitter user @dancemomLAUREN remembered an embarrassing childhood moment in which she stood up in a class and said “PARTYYYY” because the teacher left the room. Unfortunately, the teacher was still within earshot and caught her in the act!

According to Twitter user @leilethewriter, the plan was perfect and so was the cake that she baked for her sibling’s birthday. However, she made a costly mistake when she posted it on social media. Her sibling followed her on Snapchat, so the secret was revealed. At least you tried, Leila.

Also known as a water pipe, a bong is used for smoking. When asked about it, Lisa’s reasoning skills kicked into top gear, helping her convince her mom that the device was for her latest science project. 

It must have been an awkward and humiliating moment for Julie, but at least she got the name correctly spelled courtesy of the very person she was investigating.

Twitter user @Julie_Powell’s shared a funny encounter with her daughter when she was caught red-handed eating Santa’s cookies. Her daughter was visibly upset and uttered the words “Don’t do it next year!” Come on Julie, not Santa’s cookies, please.

A young mother with the Twitter account @JMKrogstad, shared a funny story about her daughter and the Tooth Fairy. Apparently, the Tooth Fairy provided some money but it wasn’t enough, so Jessie’s daughter snuck in to take some money from her mother’s purse. This was a cute but naughty move.

This teacher called in sick to work to relax at the beach only to find out one of his students was also there. They say that honesty is the best policy, but does this apply when you get caught skipping class by one of your students? 

When @boyd_kimberly was a kid, instead of consuming those vitamins, she hid them in the seat cushions. It was a perfect crime until her mom decided to clean the couch.

Apparently, the movie was so great that every time @_MarkWithAnM’s watches it, he reenacts the opening scene with his cat. Unfortunately, he left the windows open. Now the neighbors know his secret and are probably wondering when the next show will be.

According to her, she wasn’t hungry but was invited to have dinner. While the food served was mouthwatering, she didn’t have the appetite for it. So, she decided to throw her steak out of the window. The problem is, the window was closed. Who orders steak when they’re not hungry? Get a salad next time, and have the leftovers packed up to take home! 

She shared her story with Jimmy Fallon, explaining that she was working at a drive-thru at Mcdonald’s. She had a pocket full of hash browns and ate them in her car while her boss watched her. What an odd story! 

We’re sure this teenager didn’t realize that they had a determined mom with good instincts. We’re sure they had to go home right away the moment they got caught.

To his surprise, it ended up coming out as a slow whistle. This caught everybody’s attention in the library as they were staring at him. Our advice for next time? Find a restroom! 

As @CorrinneDiller shared on her Twitter page, she was not fond of those keyboard or piano lessons. So, she prerecorded the lessons to skip her practice. Unfortunately, her mom found out when she stormed into her room and the prerecorded lessons were playing. 

He looked around in all directions and was sure that no one was there. Then he released the gas from his body. The fart terrified a poor fellow who had been sitting peacefully on a nearby bench.

When Molly, who also goes by the Twitter handle @mollyligonn, was questioned by her mom, she claimed that she had been asleep all night. Little did she know that her mom had heard her clapping every 20 minutes to the theme tune of Friends. Yikes.

Unfortunately, that fraction of a second caught her on camera, and not just any camera – it was the Google Maps Camera Car, guys! This hilarious moment served her a significant lesson: wrap yourself up in a towel if you want to stare at cats after a shower! 

The young lady who shared this moment under the name @Cristyseabow stated that she was tired and dozing off when her boss caught her in the act. She was surprised but she had a plan in mind. Instead of being rattled, she just slowly raised her head and said, “Amen.” Genius! 

His younger brother has a love of drinking cold drinks. Every time his brother indulged his Slurpee cravings, he would tell him the inevitable brain freeze that ensued was because he didn’t brush his teeth. Soon enough, his little brother uncovered his dirty trick.

When @LittlebearjC spilled a bag of flour while sneaking into the cabinets, she didn’t feel like cleaning it up. Instead, she sprinkled some down the hall, leading to where her brother was sleeping. 

Their scheme was to tell the waiter that they are friends with the manager to get a discount. They were able to get away with it for quite some time before their luck ran out. They tried to use the same trick not knowing that they were talking to the manager already. Whoops! 

Twitter user @statboyslim ignored all these etiquette rules and did the unthinkable. Not only was he texting in secret about how bad the date was, but he also sent said messages to the poor girl. Things must have been painfully awkward after that! 

The store assistant, who likely assisted him on many previous visits, just spilled the beans. The poor staff member had no idea they were getting this loyal customer into the worst trouble of his married life. 

Here’s a tip: It is essential to dispose of all evidence that you cut class. Twitter user @MDavisbot forgot to do this. She skipped class to go to a mall opening but got caught because she went back to school carrying balloons that screamed “GRAND OPENING.”

To her surprise, the guy she was referring to heard her and thanked her for the compliment. Next time, don’t talk about your crush when they’re within earshot. Your chances of getting caught are too high!

Sadly, the scheme attempted by @thewildsweetpea and her friends didn’t work out so well. She skipped class and drove her pals to lunch. They were having a great time until her mom pulled up next to them at a light. 

That was a great plan, but unfortunately, her husband wasn’t aware of it. He even called her to find out where she was. That was Melissa’s undoing. Her husband and her in-laws heard her phone ringing. This young couple needs to learn a thing or two about teamwork!

For some, this might be a little bit awkward but that event probably solidified her uncle's decision to go on the date. Her aunt’s excitement could not be contained at that time, and we think that’s adorable.

Well, it worked until his boss saw him on TV enjoying the music festival he had exchanged for a day’s work. His boss made sure he got the message loud and clear by giving him wise advice: “Next time, don't stand in the front row.” Hopefully, this Twitter user has come up with some better excuses for his next getaways.

Jorge Garcia, who goes by the Twitter username @jorgelgarcia_, defied all odds and used his gas to land a job. He was in the midst of a job interview when he passed gas. The interviewer heard it, and they both laughed. The amazing part is, he got the job. In fact, the interviewer wasn’t even annoyed when he farted.

Tip: make sure you’re sending every message to the right person. Better yet, don’t discuss private matters via text. We wonder whether Jess and her friend are still friends.