First Date Disasters Real People Shared with Jimmy Fallon - too cool 2 be true

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! 

Mom’s Consent

Mojo’s date was supposed to be a fully-grown adult, but as the night wore on, it seemed his inner child was doing most of the talking. He even called his mother during the date to get her approval for the movie they were considering watching.

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! 

Clingy Son

While it’s incredible to date somebody who loves being around his family, it’s not appropriate to bring your parents on your first date. To us, Kelly’s case proves this point, but maybe we shouldn’t jump to conclusions. What do you think? Is the first date too soon to introduce your date to your parents?

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. 

Creepy Date

This date sounds dreadful. Remember people: never bring work along on a first date, especially if you’re a funeral director. We wonder if Christine stuck out the date or if she bailed when the guy popped into the office to deposit the corpse. 

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.”

Weird Confrontation

Michelle’s date had a peculiar conflict that made the remainder of the night extraordinarily awkward. The server already knew her date, and the question he asked was an uncomfortable one. 

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.

Justifying Things

Patrick accidentally spilled a soda on his pants, and when he saw his date, he needed to disclose to her that it wasn’t what she might imagine it was. All things considered, spills happen constantly. 

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.

Face Pusher

Sometimes, sharing food on dates can be an adorably intimate moment. You can test each other’s food and it’ll be a fun way to keep the conversation flowing. In this situation, however, more than the food was tested. 

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’s Honest

When Robert’s spouse said thanks to him on their first date, he gave a non-committal response that could’ve marked the end of their courtship. While you have to commend his honesty, he perhaps could’ve been a bit more tactful. 

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.


Chelsea’s date asked her for cash, which is the main thing you shouldn’t request on a first date (unless you choose to divide the bill). Worse still, this stingy fellow left the date to go buy a scratch card. 

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. 

Failed Romance

We can’t resist the urge to laugh at this story since it’s both charming and agonizing. This guy’s first date with his wife was a catastrophe, culminating in him elbowing her in the face. 

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.

Wrong Name

Having another person call you by a name that is not yours is awful. Millhouse’s date took it a step further by being wasted at the time and letting it slip that she was dating a different guy every night. That’s awkward! He must’ve felt so confused and humiliated. 

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.

Unexpected Intelligence

This young lady was not having a great time when she felt the need to push her date into conversing with her. No matter how shy you may be, it’s important to make an effort to converse with your date in order to get to know them.

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?

The Setup

Seth intended to meet a much more youthful lady for his first date, yet when he picked her up, it was an arrangement for her grandmother. This is quite possibly the strangest first date fiascos we’ve seen so far.

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.

The ER Date

Meeting your date at a bar just to wind up in the ER later on in the evening is quite a turnaround. On the bright side, Alida’s strength and grace were clearly impressive to her date. Her toe may have been broken, but at least her heart wasn’t. 

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.

Sushi Trainwreck

This woman believed that rolls implied singular pieces of sushi. An understandable error, right? Indeed, she got an unexpected outcome. Two tables were pushed together just to hold the plates of sushi she’d ordered, and she wasn’t expecting that at all. 

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.

Freaky Date

Will didn’t anticipate that his date would bring her father to the cinema. What did her father figure he needed to protect her from in such a public space? This is very odd, though we do understand the instinct to look after your children.

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.

Fidgeting Nonstop

Marc was uneasy, but his date was left thinking about what on Earth he was doing. Many things were probably going through her mind. Does he have a creature in his sweater? 

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!

Instant Rejection

Prior to going out on a date, most people like to ensure their breath is fresh. They’ll keep away from onions and garlic as these flavors can make for a horrendous first kiss later on. 

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. 

No Texting

This poor girl’s date sent her a message halfway through the evening, but it wasn’t a cute way of saying something nice. Instead, it was a message intended for one of his friends that he’d inadvertently sent to 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!

Five Words

Have you ever heard of Ernest Hemingway’s six-word stories? Hemingway was famous for being able to communicate deep thoughts with minimal words. However, Jon Sosis has one-upped the famous author, conveying the nightmarishness of his first date in just five words. 

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! 

Thanks, Ulcer!

This is the sort of disastrous date many people might actually welcome. Though she did have a disturbed stomach, Ashley’s date ended up being her spouse. 

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. 

True Love

This is the sort of story that makes us feel good inside and causes us to have faith in the concept of true love. This couple bonded over omelets, and the romance wasn’t lost when the man blew a chunk of onion out of his nose. 

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! 

Smelling Good 

Smelling wonderful is key to making a good impression, particularly when you’re going out on the town. Who would want to smell like onion soup during a first date? Jordan chose to go hard and fast and make herself smell like a sweet bloom.

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! 

Truth Matters

This is the sort of circumstance you would want to discover as soon as possible. Finding out that your date is a relative must be the most bizarre and unsettling experience.

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. 

Two Dates

Dating somebody implies that you are willing to accept their quirks, even the annoying ones. What happens, though, when your date has been disappearing all evening? You would eventually need to sit them down to find out what’s going on.

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.  

Far from Fancy

Note: It’s never alright to criticize somebody about their appearance on a first date. You have no idea what stories lie behind a person’s weight or any other facet of how they look. Besides, there’s so much more to every person you meet than how they look.

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!

From Bad to Worse

Linda was having a problematic day when she got a ticket before her date. Despite this hardship, she soldiered on, determined not to let it ruin her date. However, fate had something unexpected in store for her.

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.

No Other Choice 

Gambling is a fool’s game where you’ll usually end up on the losing end of the deal. Heather’s date is an illustration of a person who doesn’t have the foggiest idea about his limits, yet at the same time crosses them.

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. 

Strange Times

This date is an odd one since he makes reference to the girl having murdered him. We’re guessing it’s an inside joke. Murder aside, the date sounded horrendous from the start. What kind of monster gives unsolicited movie spoilers? 

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. 

The Uninvited Date

Scott’s date wasn’t who he expected by any stretch of the imagination. Possibly he should’ve seen the signs and red flags looming, particularly when she was quiet all through dinner. 

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.

Rotten Teeth

Dates can get ugly when your potential partner is a convicted criminal. In addition to the fact that it was an odd date, things got extra awkward for poor Heather when the man revealed his decaying teeth. 

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.

A Nightmare

Going to Taco Bell is one of the best fast-food treats. Their sour cream potatoes and burritos are incredible, and their tortillas are delicious. What isn’t so great is the way Margaret’s date treated her at Taco Bell.

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. 

What’s so Funny?

When you’re in secondary school, life is full of ups and downs. Your heart stops when your crush passes by, and your emotions are often at the whim of your hormones. Kyle’s high school sweetheart, however, was the sort that did not like to act on these urges. 

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.

A Party of Four

When you’re in the cinema, it’s important to be aware of your surroundings, and respectful of other people’s personal space. If someone disrespects your personal space, it can be hard to know what to do. Thankfully, Marie is here to save the day.  

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!

Ranch Dressing

Ranch dressing is heavenly on Caesar salads and chicken wings. Bennet’s date clearly thought a bit of ranch would spice things up when she went in for a kiss. Sadly, he didn’t agree. 

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! 

The Tipsy Date

Prior to going out on a date, Thomas was already drunk. This is a big no-no since you need to be mindful when you’re getting to know a new person. When he went to the restroom, everything went downhill. 

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! 

A Cringeworthy Date

Danielle’s date was attempting to be charming, yet his gesture just came across as bizarre. Here’s a tip for all the dog-lovers out there: just because a trick works on your dog, doesn’t mean it will have the same charming effect on a human you want to date! 

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. 

Supporting Her Dream

Rick’s date used him, but to be fair, there are worse ways to be used. Though we’re sure he was disappointed in the outcome, and his ego undoubtedly took a hit, this really isn’t the worst thing that could happen. 

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. 

Not a Gentleman

This young lady’s date was a major jerk. He left her stranded purely because he was embarrassed about his parking skills. Who does that? Parallel parking is notoriously difficult, so failing at it is no justification for leaving somebody in the gutter. 

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. 

Wrong Attire

Jenna was all dressed up to go to a Vikings game, and she truly went all out. With no plans of going on a date, she put all her effort into perfecting her facepaint for the game. In her head, she would soon be cheering on her team with a group of fellow fans. 

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?