Jimmy Fallon Reveals People’s Failed First Dates

Published on 10/29/2021
ADVERTISEMENT
Jimmy Fallon Reveals People's Failed First Dates

Jimmy Fallon Reveals People’s Failed First Dates

Going on a first date, especially with someone you like, can be nerve-wracking. Put on your most expensive perfumes and your brightest smile and take a longer than usual shower. Even if everything appears to be going well, mistakes can happen. A bad date is memorable, and it is unquestionably a learning experience that everyone goes through at some point in their lives. Jimmy Fallon invited fans to share their #WorstDate stories, as well as how they handled the situations. These incredible date stories will have you on the edge of your seat.

Momma’s Boy

It’s a little excessive to watch a movie with someone who is concerned about the rating. Unless they’re under the age of 18. The problem was that Mojo’s date was an adult who was acting like a child. During the date, he even asked his mother for permission.

Momma’s Boy

Momma’s Boy

She escaped a bullet there, and if her date has to ask for permission, he might want to think twice about dating in the first place. This is completely bizarre, and we wouldn’t know what to do if we were in her shoes. It’s a sweet gesture, but it’s also a little strange.

Family Guy

To be with someone who enjoys spending time with his family is a great pleasure. One of the best traits a person can have is a good relationship with their parents. But Kelly’s date loved his parents to the point that he insisted on bringing them along on the date.

Family Guy

Family Guy

This is excessive, and we believe that introducing your date to your parents should be done later in the relationship. Kelly’s date appears to have only wanted to bring his parents because he enjoys their company. He should, however, be a little more self-reliant at 25 years old…

Three’s a Crowd

This date has a creepy vibe to it. Bringing a body on a date, even if it’s in your car, is just plain awkward. Christine was fortunate enough to have the patience to sit with this man, but we would have had the chills if we had been in her shoes. It looks like something out of a horror movie!

Three’s A Crowd

Three’s A Crowd

A funeral director’s job is perfectly normal, but her date’s behavior screams strange and unstable. We’re curious about what kind of person he is if he’s okay with doing that on the first date. This is an unusual and unsettling date.

Turning Over a New Leaf

Michelle’s date had an odd encounter, which made the rest of the evening extremely awkward. We would have been confused if we had been in her shoes. The waiter knew her date, which could indicate that her potential partner is either confused or completely deluded.

Turning Over A New Leaf

Turning Over A New Leaf

It’s best to be mindful and respectful of others, regardless of your personal preferences. This waiter crossed the line and acted in an unprofessional way. After all, if you’re going to confront someone, make sure it’s not while they’re out on a date.

Mini Accident

It’s all about making a good first impression, especially on a first date. Patrick spilled soda on his private parts by accident, and when he saw his date, he had to explain that it wasn’t what she thought. Spills happen all the time, after all.

Mini Accident

Mini Accident

However, the place where it landed is a bit risky because it can be interpreted in a variety of ways. Fortunately, he was able to save face by apologizing for the spill. Things could be a lot worse; he could be wearing white pants, after all. Patrick gained a lot of knowledge from this experience.

Face Down

It’s not always a bad idea to share foods on dates. You and your date can each select a dish. Then you can try each other’s cuisines, which should be a fun experience. More than just the food was tasted in this case.

Face Down

Face Down

After her date asked her to sniff it, this unlucky lady had her face pressed into a dish. This is a huge deal-breaker and the ultimate blunder. It’s one thing to request that your date smell your food; it’s quite another to shove their food into it. This is completely unacceptable.

Robert Was Bored

When you’re upfront about what you want, honesty is a beautiful thing. On their first date, Robert’s wife thanked him and he made a remark about how little he had to do. Although this is the truth, it is not advisable to be so forthright.

Robert Was Bored

Robert Was Bored

Despite his honesty, Robert’s life turned out quite well; he was able to locate his wife. Things don’t always turn out the way we want them to, but they always work out for the best. This is a story they can tell their children, and perhaps one day they will all laugh about it.

Scratch on Scratch Off

This is a date that makes me cringe. Chelsea’s date asked for money, which is the first thing you should never ask for on a first date unless you plan to split the bill. He ditched the date and went off on his own, even purchasing his own scratch-off.

Scratch On Scratch Off

Scratch On Scratch Off

He struck it rich when he won $60, but the trashy thing he did was abandon his date in order to spend his winnings. Chelsea comes out on top in this date because she was saved from a potentially self-serving relationship.

Elbowed by Accident

Mike’s love story isn’t particularly romantic, but it’s endearing nonetheless. We can’t help but laugh at his story because it’s both adorable and painful at the same time. His first date with his wife was a disaster, especially because he elbowed her in the face, but they’ve been inseparable since then.

Elbowed By Accident

Elbowed By Accident

Sometimes all you need is a gentle nudge, but not with your elbow; that was a little excessive. When you’re nervous, it’s difficult to kiss your partner, and Mike wasn’t prepared for the kiss. At the very least, his wife stayed by his side; she’s a keeper for sure.

My Name’s Not Tom

Is there anything more terrifying than getting dumped? Someone calling you by a name you don’t recognize. When Chris’ date called him by a different name, she wasn’t in the right frame of mind. How awkward for her! He must have been humiliated.

My Name’s Not Tom

My Name’s Not Tom

To add to the commotion, his date had ten friends over at the time he wanted to take her out, and things only got more awkward when she called him by the wrong name. Chris has to be a really nice guy, and who is Tom?

They’re Watching

Have you ever wondered why some people cover their laptop cameras with tape? Some people are concerned about their personal information being stolen or their camera being secretly recorded. One of these people was Klara’s date.

They’re Watching

They’re Watching

This may or may not be true. But it’s a great conversation to start, and Klara might have learned something about internet privacy being hacked as a result. However, he dealt with the situation by placing the phone on the table, face down. Instead of making his phone look suspiciously face down on the table, he should have brought it out.

High IQ

Connecting with people on an intellectual level is always a good thing. It’s not only good for your brain, but it also makes a date ten times more enjoyable. When she felt she had to lead the conversation with her date, this girl wasn’t having a good time.

High IQ

High IQ

The energy in a conversation should be maintained by having the other person reciprocate (if they can). Her date did his best to compliment the girl, but he complimented her in an unsubtle way. That’s a huge red flag.

An Older Date

Seth had not expected his date to be 50 years older. For his first date, he intended to meet a much younger woman, but when he picked her up, it turned out to be a set up for her grandmother. Wow! This is one of the strangest first-date disasters we’ve ever come across.

An Older Date

An Older Date

We wouldn’t know what to do if we were in his shoes. We’d most likely just taken Grandma out for ice cream or something. We hope Seth learned a thing or two about picking up girls from their grandma’s house after being in such an unusual situation.

Ended Up in the ER

This was a bittersweet and painful date. Imagine walking into a bar only to end up in the emergency room later that night. That wasn’t her style, but she persisted, which her date appreciated. Even though her toe was bleeding profusely, she was able to secure a second date.

Ended Up In The ER

Ended Up In The ER

It’s awful when you’re in an accident of any kind, and it’s never a good thing. But, on occasion, good things emerge, such as this date. She expected things to go downhill, but the evening turned out to be a pleasant surprise, despite the fact that she needed ten stitches!

I’m Here!

Cassidy’s date was frantically searching the restaurant for his face. She looked for him for about five minutes in the restaurant, but when she couldn’t find him, he decided to wave to let her know where he was. We live in strange times!

I’m Here!

I’m Here!

His date became his wife, and this will undoubtedly be a story to tell the kids. “When me and your mom went on our first date, she forgot what I looked like.” What a hilarious story to tell the kids; it’s a funny moment that doesn’t sound like a bad first date.

Wrong Ride

Being an independent woman sometimes necessitates being aware of your surroundings. Anna was unconcerned about her date’s car and ended up getting into one that wasn’t his. To get her attention, he had to knock on the window.

Wrong Ride

Wrong Ride

Thankfully, the owner of the car was not present, because things would have quickly escalated if he had been. To avoid any accusations of breaking into someone else’s private vehicle, Anna should probably ask her date what their car looks like next time.

Rolling In The Deep

This woman mistook rolls for individual sushi pieces. Honest mistake, right? She got a lot more than she expected. She wasn’t expecting two tables to be set up just to hold all of the sushi plates.

Rolling In The Deep

Rolling In The Deep

Her date was probably stuffed from the sushi she had ordered. Food is always a good idea, so we wouldn’t call this a bad date. They could also have simply taken the extra rolls with them. At the very least, she learned how to properly order sushi.

Daddy’s Watching

Especially when a parent is involved, this is the definition of awkward. Will had not expected his date to bring her father to the cinema. In such a public place, what did her dad expect them to do? This is odd, and seeing her father would make us nervous.

Daddy’s Watching

Daddy’s Watching

They didn’t seem to have a second date from the looks of it. Will met her father far too soon in their relationship. We’re sure we’d be terrified if we’d locked eyes with him in the movie theater. We’re pretty sure he’s avoiding going to the movies in the future.

They’re not Mine

It’s strange to be on a date with someone who is constantly fidgeting. Marc was the one fidgeting, and his date couldn’t figure out what he was up to. She must have been thinking about a lot of things at the time. Is there an animal in his sweater?

They’re Not Mine

They’re Not Mine

It was, in fact, a pair of his mother’s underwear. How inconvenient. We’d either burst out laughing or gape open in awe. Marc is a true magician, and we’re curious about the other tricks he has up his sleeve – or should we say sweater?

Wedding Dress

Tinder is a fantastic way to meet new people from all walks of life. When things don’t work out, it’s also a great place to make new friends. Claire’s date, on the other hand, was anything but lovely. It was more of a blur because she had consumed alcohol.

Wedding Dress

Wedding Dress

She ended up helping her date’s ex-wife in selecting a wedding gown. We’re not sure what else to say if that doesn’t scream awkward! We’re curious how the first half of the date went if that was the end of the night. It’s a peculiar situation to be in.

Garlic Surprise

A few things to remember before going on a date are to make sure your breath is fresh and to brush your teeth. Unless your date is also a fan of onions and garlic, stay away from them. It could lead to a sour make-out session later.

Garlic Surprise

Garlic Surprise

Ben’s date, judging by the potentially garlicky kiss, didn’t seem too concerned about planting a kiss on him. She strewed garlic powder on her pizza slice, showing that she doesn’t want to make out with him after all.

The Ride Back

When texting your friends while on a date, it’s probably best to avoid texting in general. Maite’s date sent a text to a friend that was intended for him but was mistakenly sent to her. What an unexpected turn of events when they both locked eyes on the message and fell silent.

The Ride Back

The Ride Back

For a while, we’d have wanted to melt into the car seat and hide our faces. Oh, the humiliation. We feel bad for her date, who mistakenly believed he was sending a private message to a friend. If he regretted it, he could have told his friends after the date, but he didn’t.

That’s It, Folks

A story can be told in as few as five words. The only drawback is that we have a lot of questions. Why did he strike her by accident? What happened to cause that? We’ll never know for sure, and Jon didn’t give us a backstory or tell us what happened afterward.

That’s It, Folks

That’s It, Folks

Is she all right? Is it true that they ended up together? There are a lot of details missing here, but it appears that his story was fairly clear. Apart from the fact that he hit his date with his car, there’s not much else to say. Despite this bizarre experience, we sincerely hope she is okay.

Gracious Couple

Todd’s day got off to a rocky start when he failed to ask his date for her address. To avoid this whole mess, he should have asked her a long time ago. However, things changed for the better when he received assistance from a kind couple.

Gracious Couple

Gracious Couple

He accidentally entered the wrong house, which turned out to be a blessing in disguise. Remember when there were no cell phones, and how things were back then? Things were much more difficult, and reaching out to friends and family members was incredibly hard. It’s a good thing we have the technology now!

You Had me at Ulcer

Even if you have an upset stomach, this is the kind of date you want because things could still go well. As it turned out, Ashley’s date ended up being her partner. A wonderful twist of fate.

You Had Me At Ulcer

You Had Me At Ulcer

When you’re with someone who’s okay with stomach issues, an ulcer can become a lasting memory. Their fairytale ended with marriage and a lifetime of happiness together, so we’re not sure what else is!

Love at First Bite

This is the type of story that warms our hearts and convinces us that true love exists. Some people meet their soulmates later in life and instantly connect; this couple met while choking on an omelet and blowing onion chunks out of their nose.

Love At First Bite

Love At First Bite

While some may find this repulsive, it can be a thoughtful gesture. What better way to get to know someone than by seeing them in all their glory? Her companion appears to be a keeper, and the two seem to be a perfect match.

You Smell Good

It’s important to smell good, especially when going on a date. You don’t want to smell like onion soup or sweat on a first date, so scents should be applied liberally. Jordan decided to go all out and smell like a sweet flower.

You Smell Good

You Smell Good

Her date complimented her on how nice she smelled, but she was also very nervous. She told him how she breathes instead of accepting the compliment. It’s a little silly, but it’s also a little cute. This worst date doesn’t appear to be all that bad, and it could be a lot worse.

The Discovery

This is the type of situation where you should be grateful that you found out sooner rather than later. It’s a big no-no to date a relative, so this person was lucky to catch on before it was too late. One of the strangest things we’ve ever read is finding out your date is a relative.

The Discovery

The Discovery

This is the worst date story I’ve ever heard. Sure, it’s revolting to date someone who burps and farts for the first time, but the most sickening experience is dating someone who could be a relative. We would have felt so uncomfortable during that family BBQ.

Double Trouble

When you go out with someone, you have to put up with their inconsistencies as well. But what if your date has been inconsistent the entire evening? This necessitates an investigation to determine how he is faring in real life.

Double Trouble

Double Trouble

The waiter was conducting her own investigation, and she is likely to encounter this situation on a regular basis. She approached Kelsey and informed her that her date was a con artist because he was seeing two women at the same time. Kelsey had a true lifesaver in her!

Rude Comments

Making a big deal about someone’s weight and being so forthright about it is never a good idea. First and foremost, the person may be suffering from a serious illness and be wary of disclosing personal information. Catherine’s date didn’t have a filter and spoke without restraint.

Rude Comments

Rude Comments

It’s great to be direct and say exactly what you need, but you also have to be cautious about what you say. Catherine acted rationally, despite the fact that she could have simply left. She poured a drink into his lap and showed his immediate karma.

Ticket Guy

When Linda received a ticket before her date, she was already having a bad day. When you get a ticket from a cop, it’s a pain because they can sometimes take your license away, putting you in an even deeper hole than you were before.

Ticket Guy

Ticket Guy

When Linda discovered that her date was the cop who had issued her the ticket, things went from bad to worse. What are the possibilities? We hope he was able to get the ticket revoked and let this one slip by. After all, isn’t chivalry still alive?

The Gambler

People who have a gambling problem can have serious consequences in their personal lives. Gambling is a tricky game in which you will always come out on the losing end. Heather’s date is an example of a man who has no idea what his limits are and continues to push them.

The Gambler

The Gambler

Heather was forced to pay for the date because he had lost all of his money gambling. Supporting someone’s gambling problem is never a good thing, but Heather had no choice but to pay for the date despite his obvious gambling addiction.

Not Your Dream Girl

This date is unusual in that he claims she murdered him, but this was obviously a joke. If she dropped a spoiler for the movie’s ending, the date must have been a disaster from the start. Spoilers are annoying because you want to see a film for yourself.

Not Your Dream Girl

Not Your Dream Girl

Collin’s date was the polar opposite of a dream girl, and she didn’t seem to care about the date in the least. It can look really bad and make things uncomfortable if you don’t eat dinner on a date. If we were Collin, we’d avoid dating again or at the very least screen potential dates before spending time with them.

The Mysterious Date

This date sounds like it could have come straight out of a suspense film. Scott’s date isn’t at all what he had hoped for. Perhaps he should’ve noticed the warning signs earlier, especially when she was silent and didn’t speak to him during the meal.

The Mysterious Date

The Mysterious Date

When he realized his date wasn’t the girl he was with, he ended up eating with a complete stranger. What a strange turn of events this has turned out to be! First and foremost, how could he have missed the fact that she didn’t look like her picture? We still have a lot of unanswered questions about this enigmatic date.

Prison Time

When your potential partner is a convicted felon, dates can take a turn for the worse. Not only was it an odd date, but we have a feeling Heather was uncomfortable with the guy as well. Especially considering his decaying teeth.

Prison Time

Prison Time

Perhaps he should have brushed his teeth and gargled with mouthwash? That would have undoubtedly solved the problem. But he didn’t even pay attention to his hygiene, which is a huge turn-off. Heather should’ve brought him some mints or chewing gum to give him.

Taco Bell Nightmare

Taco Bell is the best, especially if the sour cream potatoes are still available. Their burritos are incredible, and their tortillas are simply outstanding. Margaret’s date’s treatment of her wasn’t up to par, and it was downright rude.

Taco Bell Nightmare

Taco Bell Nightmare

For their first date, he took her to Taco Bell, but he decided to eat and leave her. Worst of all, he was cheap about it, and the second-worst was when he abandoned her. She deserves a lot better than her date, and he wasn’t even worth her time.

Rejected

You see everything through rose-colored glasses when you’re in high school. When your crush walks by, the hallways become brighter, and your heart slows down. Kyle’s high school girlfriend, on the other hand, was not the type to express affection.

Rejected

Rejected

She thought it was a joke when he tried to kiss her. His gesture was sweet, but she dismissed his request with a laugh. Early rejection helps you manage expectations as you get older, and Kyle’s ex had just taught him a valuable lesson about love and relationships.

Four’s a Crowd

It’s always important to be aware of other people’s needs when you’re in the theater. It’s critical to be aware of your surroundings, especially when you’re eating popcorn or talking too loudly. The only problem is that Marie’s date didn’t go as smoothly as she had hoped.

Four’s A Crowd

Four’s A Crowd

Two more guys decided to join the party when she went to the movie theater. She wasn’t sure about that and inquired if they were all dating at the same time. Even though it was a witty remark, we can imagine the awkward silence that followed. Yowza!

Salad Anyone?

When you dip your wings in ranch dressing, it’s amazing. It would also be delicious on top of a Caesar salad with croutons. Kisses, on the other hand, do not go well with it, and Bennet’s date tried to lean in and plant a big kiss on her lips.

Salad Anyone?

Salad Anyone?

The only disadvantage of the situation is that he still had food in his mouth. Gross! At the very least, make sure your food is completely swallowed before kissing someone. Birds are probably the only animals who would be okay with it. As a result, when he spooned ranch into his mouth, the date was officially over.

Have We Met Before?

This is the ultimate cringe moment. Thomas went on a date and got a little tipsy in the process. On a date, this is a big no-no because you want to be fully aware of their presence and conversations. Everything started to fall apart when Thomas went to the bathroom.

Have We Met Before?

Have We Met Before?

He saw his date but asked her out again, which must have made her feel very awkward. We’d go with it and see how long it took him to remember if we were in her shoes! This is a fun date moment that will be remembered for a long time.

Puppy Trumpet

Another dreadful date, oh no. Although Danielle’s date was trying to be cute, his gesture came across as odd. Who invents a puppy trumpet by blowing into someone’s nose? While his may appear cute at first, it appears to be a gesture reserved for a more serious relationship or something that will never be repeated… we won’t say.

Puppy Trumpet

Puppy Trumpet

This was a cute gesture, but we wouldn’t advise following in his footsteps. It’s one thing to kiss someone’s nose, but it’s quite another to blow it. Everything seemed fine up until this point, but then things began to cool down.

Crackers and Mario Kart?

When he said he was clueless, he wasn’t lying; he was completely clueless. On a first date, you usually try to impress your potential partner with the best of the best. But, as part of their date night dinner, this guy didn’t even try to level up with the saltine crackers.

Crackers And Mario Kart?

Crackers And Mario Kart?

While it’s a sweet gesture, that’s no substitute for a proper meal. After that, she must have been hungry, and it’s more of a snack to share with the boys. On a first date, you shouldn’t play video games because you won’t be able to talk to them or get to know them. By the looks of it, he left her in the friend zone.

It’s The Nun Life For Me

People who aspire to be priests or nuns are taking a big step toward a life of celibacy and no dating. Rick’s potential date wanted to see how the waters were before entering the convent, and she did just that. The only problem was that it was going to be her last date.

It’s The Nun Life For Me

It’s The Nun Life For Me

At the very least, Rick had a date with the super cute girl. Isn’t that what matters? The date didn’t appear to be all that bad; she just had pre-existing goals that surfaced afterward. If anything, this experience was beneficial to both of them!

Boy Bye

This girl’s date wasn’t a gentleman; in fact, he proved to be a jerk by picking her up and then leaving her! Who is it that does that? Just because he couldn’t find a parking spot three times doesn’t mean he can just abandon someone on the sidewalk. Come on, this isn’t cool at all.

Boy Bye

Boy Bye

If we were Leslie, we’d expect him to at least make amends by sending a large bouquet of flowers to her house. We hope he apologized, because if he left her the next day without saying anything, the only thing Leslie should say is, “Thank you next.”

Wrong Date Attire

Nothing makes a potential date more awkward than showing up in the wrong date attire. Jenna was all dressed up and ready for a Vikings game, but it wasn’t one. She had gone to great lengths to prepare herself, including smearing face paint on her face, only to find her date waiting for her in a posh restaurant.

Wrong Date Attire

Wrong Date Attire

Yikes! This is a disaster waiting to happen. We’d escort ourselves out the door if we were in her shoes. Her outfit and attitude were cute, but it wasn’t the right time. For everything, there is a right time and a right place, and this was neither.


ADVERTISEMENT