People Told Jimmy Fallon About Their First Dates That Went Oh So Wrong

By Doreen R

Nearly everyone who’s been on the dating scene has an interesting tale to tell. Late-night talk show host Jimmy Fallon is responsible for #WorstFirstDate, which has gone viral. We simply can’t get enough of disastrous first dates. From the girl with the ulcer who burped and farted on her first date to the guy who rear-ended his date with his car, everyone’s got a story to tell. Whether these couples made it to the altar, you’ll have to read and find out for yourself. Some dates should never have taken place, like the guy who had two first dates simultaneously, only to be outed by the waiter at the restaurant. Some dates are downright creepy, like the guy who ended his date only to find a message from his date saying she couldn’t meet him. We have collected a wide array of first dates gone wrong for your enjoyment. We’re happy to say that some first dates are heartwarming with happily ever after endings that can’t help but make one believe in true love.

A Real Mommy’s Boy

For some women, dating a guy that’s close to his mom usually sets off warning bells. Imagine this gal’s shock when her date called mommy to find out if he could see a rated-R movie. It might have been okay if he was, say, 14 or 15 years old, but certainly not 21.

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Mojo Jojo’s first and last date was worthy of making it on Jimmy’s list, and for that, we’re grateful. Ladies, the tip of the century; if your date is legally allowed to vote and drink yet still calls mommy to ask about seeing an adult movie, run! This is a forewarning of things to come. Get Out!

Meet the Parents

Sure we all want to be with someone close to his family. It’s a good sign when our significant others enjoy spending a lot of time with their siblings and parents. However, timing is everything. From Kelly’s tweet below, once she got over the shock of her date bringing his parents, there was more to follow.

Image courtesy of KellyScicluna/Twitter

Kelly loved the fact that her date was close to his family. She even managed to muddle through their first date with his parents. It was when the mom decided to take home the leftovers from the restaurant that Kelly saw enough. Sure, doggie bags are acceptable, but there’s something odd about bringing your own aluminum foil to wrap the remaining food.

Don’t Mind the Dead Body in the Back

It’s hard to make a living, and we’re all about supporting our partners in keeping the paycheck coming in. Sometimes, though, it’s okay to take a break and focus on a date, especially a first date. Poor Christine was in for a shock when her first date with a funeral director showed up with a dead body.

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Creepy enough to date someone that deals with the deceased. Someone’s got to do it. We get that. Let’s get real though, a first date is all about first impressions and putting our best foot forward. We can’t say this enough folks, do not show up to your first date with a dead body in tow.

Picking the Locale for the First Date is Crucial

The reason the #WorstFirstDate is so popular is that it’s eye-opening and humorous. Thankfully, Jimmy Fallon’s fans aren’t shy about sharing their shocking first dates with the world. This one made us giggle and then roll our eyes. This guy should’ve considered a place where he’s less recognizable.

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This isn’t about being into the opposite sex or even sexual preferences. It’s about making a good first impression. If you’ve been upfront about your lifestyle, that’s great. If you’re undecided, then things can get a bit awkward. Michelle found out the hard way that her first date wasn’t fully decided. Thankfully, her date took her to his favorite hangout and made it to Fallon’s infamous lineup.

It’s Not What You Think, Honest

It’s totally a given that we primp and prepare to make the best first impression on first dates. It’s the first impression that will likely set the tone for the relationship. It’s not uncommon to have lipstick on our teeth, a tear in our pantyhose, or even a wet crotch. Hold on, what?

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That’s right, Patrick was driving to his date when he poured some soda on his crotch. Obviously, there was no turning back to swap for a dry pair of pants. We can just imagine his date’s face when his first words were, “It’s not pee.” If they ended up happily ever after, this is a great story for the kids and grandkids.

Dude, Grow Up!

For most, a sense of humor tops the list of must-haves in our partners. Some argue a sense of humor is more important than looks. We can understand that thinking. Good taste and humor, though, are a winning combination. This guy obviously didn’t get that memo.

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We’re not sure what this guy was thinking, but we’re pretty sure he hasn’t fully matured quite yet. Note: smashing the wedding cake in your partner’s face might work on your big day, but even that’s becoming passe. Pushing food in your date’s face the first time you’re out together is a big no-no. Advice to date, grow up asap!

Think Before You Speak, Robert

Up there, with humor, honesty is essential in making a relationship work. Knowing what to say and when should also be considered, even if it’s laced with honesty. We love Robert’s humility here and the fact that he and his wife survived their first date, and his brutal honesty, which shows they’ve got what it takes.

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We thought it wasn’t wise for Robert to admit he had nothing better to do on his first date, but his date must’ve seen something beyond. Here’s hoping Robert learned to navigate and think before he speaks. They’re married several years, so we’re not judging. Oh, wait, yes, we are judging.

Tip # 23: Do Not Ask For Money On First Date

We have to hope that Chelsea didn’t end up with this guy. Her first date sounds like a real loser. It’s bad enough he didn’t have cash for his first date, but the string of events to follow should be a wake-up call to many guys. We can’t argue with the funds part, especially when we live in an era when women are just as equal to men in all aspects.

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It’s totally acceptable to split the bill on a first date, but to show up with empty pockets isn’t okay. To borrow money for a drink is questionable, but buying a lottery ticket is a bit odd. He got excited about winning a few bucks and decided to scrap the date and head to the strip club is a bit concerning. Chelsea, how lucky that you saw your date for what he truly is, and it only cost you $10.00.

That’s Embarrassing!

We love when bad first dates end up in wedding bells. That’s the case with Mike and his wife. It might’ve been a tragic first date, but his future wife saw more than just a bumbling and clumsy guy. First dates are bad enough, and there’s a reason we’re not supposed to kiss on the first date, and Mike can explain why this rule continues to exist.

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First date jitters are a given, especially if we’re digging the person sitting across from us. It’s okay to sweat a little, be nervous, and be downright awkward. While most women wouldn’t think twice about giving a guy who clocked them in the face a second chance, this gal saw something more. Either way, we loved that this tale has a happing ending.

Tip #55 Know Your Date’s Name

We’ve seen this joke played out far too many times in movies where the guy can’t remember his date’s name. Films reflect real life in many cases, as they did in Chris’s experience. Showing up at his date’s front door and realizing she didn’t remember his name, Chris realized she might not be ‘the one.’

Image courtesy of ChrisMillhouse/Twitter

First dates are known for awkwardness and embarrassing moments. To not remember your date’s name, though, is pretty funny. From what Chris states, his date seems to have needed a drink or four before their date, which could explain her confusion. The fact that she admitted she’d got a roster full of men might not bode well with a lot of men.

Shh, Big Brother is Listening

The web is chock full of stories about couples meeting online. Some are downright fairy tales, while others are insanely wacky. Meet Klara Cee, who didn’t do enough checking on her date before meeting up. Online, her date seemed witty and clever. Once the keyboard disappeared, reality hit hard.

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Klara found out her date was not only paranoid and suspicious of anyone and everyone. He was sure he was being watched. Just so we’re clear, taping up your phone probably won’t do much if we’re really being watched. While Klara’s date might be on to something, we’re more sure that this guy’s not playing with a full deck.

Wow, Looks and Brains, You’re the Full Package!

Meeting online has its pros and cons. Some feel that you really get to know a person while texting back and forth. We’re not so sure. It seems like we can create a persona that’s not steeped in reality when hiding behind a screen. We’ll let you decide, based on this first date, gone wrong.

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This dude lost points by showing up late and even more when he wasn’t eager to buy his date a coffee. It’s when he blurted out that the woman sitting in front of him was brighter than he thought that we lost faith in him. It’s okay to be attracted to brains, but stating that you thought you were meeting a moron isn’t going to score you any points.

She’s Not Looking To Be Anyone’s Trophy

Sadly, it’s a fact of life. Older men like dating younger women. We might not like it, but it happens, so let’s accept it. Or maybe, we shouldn’t be so quick to accept it. We love how Seth was put in his place by his younger date. Seth was looking to date a younger gal, only to find out she had other plans.

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Seth was put in the ‘dirty old man’ category creatively. When he went to pick up his date at her grandma’s house, he was in for a surprise. While we don’t know how the evening ended, we couldn’t help but cheer on this lady who put this man in his place. We’d love to have been a fly on that wall when Seth realized he was expected to take grandma out on a date. Place laughing emoji here.

Ouch, That Hurts!

Alida had high hopes for her first date. It was set to take place in a bar, and she got all dressed up and was on time. We’re thinking maybe she was feeling a bit awkward, took a little stumble, and stubbed her toe. Usually, not a big deal, could happen to anyone.

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The stubbed toe wasn’t a big deal till she realized it was worse than she thought. The toe began bleeding, and she realized things are not good. She did, however, get a second chance to make a good first impression. Usually, these are stories to be told at the Golden Anniversary. We’re not sure how this ended, but at least the duo gave it another shot.

Hey, Over Here!

There’s a moral to this story, and you’re soon going to learn it. When meeting a significant other online, honesty and transparency are key to a successful relationship. This applies to photos of us as well. Meaning, let’s use fewer filters and good lighting and be upfront about how we really look.

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While we can’t be 100% sure that this couple met online, it does seem to point in that direction. Considering Cassidy’s date was wandering around the restaurant for some five minutes looking for her date meant something was up. The result of that bad first date ended in marriage, so she seemed pleased with what she found that night—a great story to relive each anniversary.

Sometimes It’s Okay To Let the Guy Lead

We’re all for women’s rights, but sometimes it’s okay to let the man lead. It’s even more okay when it saves on an embarrassing moment. Anna tried to prove she’s an independent, strong woman, but in the end, it may have bitten her in the rear.

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Had Anna waited for her date to lead her to the car, she might not have gotten into the wrong vehicle. While it’s not the end of the world, we’re sure she felt a bit foolish. Let’s hope both brushed it off and moved on.

A Little Research Might Have Helped

Thanks to the Internet first dates are awkward enough, but they don’t always have to be. Had this lady done a little research before her date, she might have known that 13 rolls of sushi were too much.

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For most, it’s common knowledge that an average sushi roll consists of 4, 6, or even 8 pieces. While it’s funny enough, you’d think the waiter should’ve advised a couple against ordering 13 rolls. Our tip here would’ve been to check out the menu before arriving, and this entire saga would’ve been prevented. But, then it wouldn’t have made our list, just sayin’.

Hint: Leave Dad at Home on First Date

This first date has got to be in the top 10 of #WorstFirstDates. We can’t imagine in what universe bringing one’s father to a first date would be acceptable. The fact that Will’s date kept looking at her dad is pretty weird as well.

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Most people feel uncomfortable enough on a first date, but having a parent close by has got to be a major buzzkill. Let’s just hope the movie wasn’t R-rated because that would be a reason for even more unease for all involved parties.

No Idea How That Got in There

Considering most check and double-check their appearance before heading out, this is too funny for words. Marc must’ve been rushing and didn’t notice that something was stuck in his freshly laundered sweater. Had he checked before leaving home, he never would’ve ended up here.

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Many of us have had that strange sensation that there was something off with our clothes. For some, it might be a stray used dryer sheet. Poor Marc must’ve wanted to bury himself when he pulled out his mom’s underwear from his sweater. Let’s hope this was a one-time occurrence or that he was serious about doing his own laundry.

Meeting the Ex-Wife On the First Date

Anyone who’s ever used Tinder knows that anything can happen. For some, that’s the attraction to using the popular dating site. Ending up meeting one’s ex-wife on a first date, though, might rank as super weird, but let’s not judge.

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Claire knew she was meeting a divorced guy but had no idea she’d end her date at his ex’s place. Thanks to a little too much booze, she not only met the ex but helped her pick out her wedding dress. Talk about a friendly divorce.

She Doesn’t Kiss On the First Date

We’re all about being upfront and honest and meeting expectations. Ben realized quickly where he stood with his date. We can’t help but think Ben’s date should’ve been upfront about not kissing on the first date. His date might have taken things a little too far.

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It’s also a bit presumptuous of his date to assume Ben was even that into her. Maybe he wasn’t feeling the warm fuzzies and had no plans beyond a pleasant handshake at the end of the date. If she could say she wasn’t going to kiss him later on, she didn’t need to proceed and pour stinky garlic over the pizza.

Always Review Before Pressing Send

We can all relate to this. Emailing or texting the wrong person accidentally happens to everyone, at least once. This guy obviously didn’t check who he was texting. Oops is an understatement in this case. To read that the guy you’re on a date with isn’t that into you while it’s happening is a bit awkward, to say the least.

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Maite must have wanted the ground to open up when she realized what her date thought of her. Don’t feel bad, Maite. Your date probably felt even worse. We love that he had to drive you home after that text as well. Talk about uncomfortable.

We Need to Know If They Exchanged Details

While we’re not sure how this date ended, we are hoping there were no casualties. Starting the first date with a car accident usually means things will go south from there. Hitting your date’s car, though, is even worse. We wish Jon gave us a few more details.

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Sure it’s not ideal to start a relationship with a fender-bender. We really wish we had more information here because this isn’t necessarily a deal-breaker. From the sound of it, though, the date ended there. We can’t help but feel that this would be a great story to tell on their 50th wedding anniversary. Jon, if you’re reading this, give us more info!

Aww, They Sound Like a Nice Couple

Many of us can’t remember a time before we had mobile phones. Those of us that can have to remember TGIF. This tale had us oohing and aahing by the lovely couple that invited Todd into their home. They sound adorable.

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Today, not many people would enter a stranger’s home to make a call, but it must’ve been a simpler time back then. We now are left to wonder what happened on Todd’s date. Did he get the right address, or did he stick with the couple and catch up on the latest episode of Full House? We now need updates on these first date Tweets!

He Married the Girl Who Farted On Their First Date

Ashley’s first date could’ve gone so differently. To be diagnosed with an ulcer, put on meds that cause farting and burping, and still go on that first date, wow. We like Ashley more and more. We’re also digging the guy who saw past her ulcer.

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We’re glad Ashley didn’t take her doc’s advice by resting while getting used to her meds. We can’t help but appreciate her date, which saw beyond what must have been an embarrassing first date. The fact this ended in marriage makes us hopeful that true love can happen to us all.

Talk About a Happy Ending

We’re not sure what Maureen thought when on her first date, the guy nearly choked. If that’s bad enough, to have onions flying out his nose must have really sealed the deal. Maybe it was nerves, or maybe the food went down the wrong tube, but he thankfully survived.

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Not only did he survive, but he also married Maureen. The icing on the wedding cake is that they have a great story to tell everyone. We love when true love wins over shallow-minded individuals. Some might have been freaked out and ended it right then and there, but not these two. We wish them many years together and hope they got their happily ever after ending.

Well, That’s An Interesting Reply

This first date is definitely funny. It’s totally normal to be nervous and to not think before we speak when meeting new people. Jordan’s reply to her date telling her she smelled good is absolutely priceless. It’s hard not to do a double-take when reading this Tweet.

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Some people get nervous around new people. It’s completely normal. Seem that this is what happened to Jordan. When he told her she smelled good, she took him literally instead of thanking him and her perfume. She’s also nothing if not polite. She uses both her nostrils to smell good! Come on, it’s funny!

We Are Family

The hit classic song We Are Family by Sister Sledge applies here perfectly. What a small world it must be when your date takes you to a family bbq, and you find out you’re all related. Sounds more like a family reunion than a first date.

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We’re not sure how creeped out these two became when they found out they were cousins. Kissing cousins takes on a whole new meeting after reading this tweet. Even if romance didn’t develop. We’re hoping they kept in touch.

Men Can Multitask

Whoever said men couldn’t multitask hasn’t met Kelsey’s date. While she thought it was odd that her date kept disappearing to the bathroom, she certainly didn’t think he was on another date. She must have thought her guy was really busy constantly getting up to take a call or visit the restroom.

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We love that their waiter was observant and was watching out for Kelsey. We’d love to know if his other date was aware of it as well. We thought dates like these only happened in comedy shows or movies. Obviously, these scenarios are steeped in reality.

Dude, Think Before Speaking!

Women have enough issues to deal with. This is a tip to all the men who don’t have the smarts to think before blurting out what’s on their minds. Never, and we mean never, comment about a woman’s appearance, under any circumstances.

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Kudos to Catherine for not letting that idiot’s comment get to her. We love how she thought quickly and didn’t waste time putting her ‘date’ in his place. Ladies, never let an insensitive guy’s comment get to you. Learn from Catherine. We’re sure that dufus will think twice before mentioning a woman’s weight again.

He Should’ve Cancelled the Traffic Ticket!

This is the definition of ‘coincidence.’ To get a traffic ticket before a date is enough to put anyone in a foul mood. Finding out your blind date is with the guy who gave you the ticket is beyond hysterical. It didn’t happen to us, so it’s easy to laugh it off.

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Linda must have had a few harsh words for the friend who fixed her up. We’d love to know how the date went and if the cop had the decency to at least cancel the ticket. This first date gone wrong should rank in the top 10 for sure.

Dressing to Impress Wasn’t An Option

The majority of us have experienced dates we’d love to forget. Heather’s date is one of those. Being picked up in a car that most likely smelled of fumes and finding a guy with a shirt full of holes, Heather surely wanted to get away asap.

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To find out her date had a gambling problem also wasn’t ideal. Why she got in the car is beyond our comprehension. Pretty sure there wasn’t a second date. Heather seems like she’s a sport, though, because she did pay for the date. Hard to imagine she could do any worse.

First Degree Murder on First Date

Colin may have exaggerated about his date, but we lol’d nonetheless. It’s safe to say Colin isn’t a fan of Nickelback, but to equate that with murder is taking things a bit too far. We are wondering if he tweeted these details just to make a list.

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From the Tweet, it’s obvious Colin was peeved at having the movie ruined. While this guy might get the title of Drama Queen, we’d love to hear his date’s version of events. We’re assuming that just being a Nickelback fan was enough to ruin Colin’s night out.

A Blind Date With a Creepy Ending

This tale is sure to cause goosebumps. Scott was waiting for his blind date to show up for dinner. He had no idea what she looked like, but she showed up, and they dined together. He had no idea when the date ended. He’d discover the lady he was dining with wasn’t his blind date.

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This made the hair on the back of our necks stand up. We can’t even imagine what Scott felt when he saw a message from his date saying she couldn’t make it. It does make us wonder who Scott was having dinner with. Thankfully, he survived the date to tweet about it.

At Least He Didn’t Open With His Mug Shot

Poor Heather having to look at her date’s pictures and learning he’s an ex-con all in the same evening. While we’re not sure how it ended, by the looks of it, we’re hoping Heather’s moved on to bigger and better prospects.

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Look, we’re not judging this guy, who may have done his time and is now a productive member of society. We are judging that he tried to impress his date by showing pictures of his ex and displaying a mouth full of rotten teeth. Heather should be glad she saved a lot of money in fixing his smile.

Value Menu + First Date = Disaster

We’re not dissing on anyone trying to save a few bucks. If you’re out to impress, a place with a value menu might not be ideal. To impress on a first date, it might be best to discuss where that date will take place. Nothing wrong with Taco Bell, but maybe not for the first date.

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We’re not even getting into looking cheap by taking your date to Taco Bell. Dumping your date at Taco Bell, though, reassures us that Margaret dodged a bullet. We’re glad she found out soon enough that her date wasn’t worth all that much to begin with. Hopefully, she’s found the guy that was willing to splurge on a full-price dinner.

At Least He’s Polite!

Dating, in general, is tough. We learn as we go along, and hopefully, it gets easier with time. Dating in junior high or high school is cringe-worthy for the majority of humans. Manners are a must on a date. Laughing at manners isn’t a must, and we should think twice before making our date feel bad.

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We felt for Kyle when we read his tale. He finally gets that date with the girl of his dreams, only to be slammed. Many would think it’s adorable to ask if it’s okay to kiss before assuming. Sadly, Kyle was laughed at for asking his date if he could kiss her. Without knowing the gal, we’re rooting for Kyle and hope he ended up with someone who appreciated good manners.

Personal Space Is A Real Thing, Remember That

Some guys need to really check themselves. Especially when they see two women together. Just because two women are together doesn’t mean they’re on the prowl for a husband. Just ask Marie, who was at the movies with her gal pal.

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For some unexplainable reason, two guys saw two gals sitting together and thought that meant they could just cozy up to them. Good for Marie, who wasn’t intimidated and spoke her mind. Let’s all remember we’re entitled to our personal space. Had they asked if it was okay to sit by them, they might not have been brushed off so quickly. Tip to the men: know your audience.

Nearly Everyone Loves Ranch, Right?

The beginning stages in any relationship are thwarted with awkward moments. Deny it all you want. Everyone’s got a funny story or two about dating. Kissing your date is usually the highlight in the early stages, or at least it should be.

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Many of us prepare for kissing our dates; whether we pop a mint or take a swig of mouthwash, we aim to please. But when your mouth is full of ranch dressing, that’s when you should rethink planting a big wet one on your partner. According to Bennet, the girl tried to kiss him with a mouthful or dressing. We’re assuming he didn’t lean in and seize the moment. Maybe he favored Vinaigrette more.

Too Much Booze Isn’t Good For Anyone

It’s normal to be nervous about a first date. It’s okay to knock back a drink to calm one’s nerves. However, when you don’t remember your date, then it might be time to slow down. That’s what happened to Thomas, who may have one or five drinks too many.

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Thomas admits to indulging in a few too many drinks before his first date. Just how many are too many? That’s the question. Safe to say, if you can’t remember your date’s face, you’ve hit your limit. He really tried to imagine the gal’s face as he exited the bathroom and tried to hit on her.

You Better Check Yourself!

Bizarre first dates are the crux of this story. The weirder, the better. Danielle was surprised at how her date progressed, and we’re just as shocked as her. Danielle was sure that the animal-loving guy she was meeting was going to show her a great time. She figured he loves dogs, so he must be a stand-up guy.

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While the date seemed to go okay, the end of the night is where things got a wee bit strange. What she assumed was a kiss goodnight turned into something awkward and unexplainable. The fact that he did the same to his dog is also a tad concerning. Tip to the dog lovers: ‘puppy trumpet’ is not a thing and should not be attempted!

Even the Great Jimmy Fallon Has a Story

We mere mortals seem to put celebrities on a pedestal for no reason whatsoever. We assume that celebs can do no wrong and are wise to dating and romance. That’s not always the case. Just ask Jimmy Fallon. The late show host and comedian is quick to share his lack of charm for the ladies.

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We’re thankful here that Jimmy proves that even big-name celebrities are only human. Some women might be thrilled to play video games and eat saltines on a date with a celeb, but we’re sure you need the star status and paycheck first. Had this date happened when the comedian was already a respected comedian, it might have been easier to digest.

Now That’s a First

In college, it’s only natural not to be decided about our future. It’s a time to look inward and decide a path that’s best for us. Rick had no idea he’d be losing his gal to the Almighty himself. On their first date, his date let him know that she was considering devoting her life to the church.

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From reading this Tweet, we can’t help but wonder what happened to make that young lady decide to become a nun. Whatever it was that Rick did, it couldn’t have been good for his ego. We’re hoping it did give him some insight, and he’ll behave differently from here on.

LOL, Men Aren’t Better Than Women at Parking

This is yet another #WorstFirstDate saga, but with a funny ending. A lot of women have heard, far too many times, that men are better drivers. We’re not debating that sensitive topic, but we are showing that it’s not steeped in fact. While this date ended badly, it also gave this woman more than a hint of satisfaction.

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Leslie was waiting patiently while her date parked the car. She had no idea that when he couldn’t parallel park the car, he’d drive off in shame. He gave it three valiant tries but wasn’t able to squeeze his car into a space that most likely a woman would’ve found no problem getting into. This is for all the women who were told that men are the better species.

Tip #12 Know Your Audience

This first date is too funny for words. Jenna must have gotten her signals mixed up, big time. To think she was meeting a group of people for a football game only to find out she was way off is a bit bizarre. We get that it’s sometimes hard to gauge a text or any online message. However, to read something so wrong is baffling.

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We’re honestly trying to figure out what Jenna understood to result in her painting her face with her team’s colors and dressing the part, then enter a five-star restaurant, thinking it was okay. We’d also have loved to see her face when she realized she got it so wrong. We were also picturing the other diners’ faces when she entered the fancy establishment in her getup.