In the never-ending quest for true love, many must endure a seemingly endless parade of first dates until they finally find the one person who is just right. While some may enjoy the butterflies and excitement accompanying first dates, most would agree that they can be awkward, uncomfortable, and occasionally dull or cringe-worthy. Indeed, the initial stages of romance often feel like navigating a battlefield fraught with challenges and surprises.
Recently, Jimmy Fallon invited his fans to share their funniest, most embarrassing, and cringe-worthy first date stories in honor of Valentine’s Day. The resulting tales provided much-needed comic relief, proving that even the most disastrous dates can lead to laughter and camaraderie. Surprisingly, many of these hilariously awkward encounters blossomed into lasting relationships, demonstrating that love can conquer all. So, gather around and prepare to chuckle as we share these amusing anecdotes that redefine the term “battlefield of romance.”
#1: The Double-Date Deception
It’s often said that truth is stranger than fiction, and this tale of multi-tasking certainly proves it. One woman found herself on a date with a man who was simultaneously dating another woman at the same restaurant. This level of deception takes sleaziness to a whole new level.
Frequent trips to the restroom or unexplained absences during the date should have raised suspicions, but who could have imagined such a scenario? Thankfully, a helpful waiter clued her in, allowing her to exit this bizarre situation quickly.
#2: The Mysterious Blind Date
Blind dates come with their fair share of risks, but this story takes the cake for surprises. This individual enjoyed an entire dinner with their blind date, only to discover at the end of the night that the person they were supposed to meet never showed up. The fact that their dinner companion remained silent throughout the evening should have been a red flag, but hindsight is always 20/20.
When embarking on a blind date, it’s wise to obtain a detailed description of your intended date to avoid such bizarre encounters. As for the mysterious dinner companion’s motives remain a mystery – was it a dare or simply a ploy for a free meal? We may never know.
#3: A Bold Retort
This story likely begins with a couple meeting through a dating app and seeing each other in person for the first time. Upon introduction, the woman’s date rudely commented on her weight, saying, “I thought you’d be thinner.” Reactions to such an insensitive remark could range from freezing to crying or slapping the offender.
However, this woman’s response was nothing short of brilliant. She poured his drink into his lap and retorted, “I thought you’d be smarter,” before turning on her heel and leaving. Her bold move put the rude date in his place and demonstrated her resilience and wit. Ending the night with pizza seems like a victory in this case.
#4: A Date with the Law
Receiving a ticket is always a frustrating experience, and this woman hoped to put her earlier encounter with law enforcement behind her as she prepared for a big date. Little did she know, her blind date would be the same police officer who had issued her the ticket earlier in the day.
The situation was undoubtedly embarrassing for both parties, but it’s important to remember that just because he gave her a ticket doesn’t mean they couldn’t enjoy their time together. After all, she may have been at fault as a driver, and the officer was merely doing his job. Their awkward introduction doesn’t necessarily preclude the possibility of a connection.
#5: Misdirected Messages
We’ve all experienced the awkwardness of texting the wrong number at some point, whether accidentally sending a message meant for a family member to a landlord or sharing a private text with a group chat. In this case, a man mistakenly texted his date instead of his friend, discussing the ongoing date.
While the situation was undoubtedly cringe-worthy, it’s clear that the date wasn’t going well, and the unfortunate text mishap hastened the inevitable conclusion. There are, of course, many better ways to let someone down gently.
#6: Culinary Connection
First dates can be nerve-wracking, especially when inviting someone for a home-cooked meal. In this case, a woman took a chance and prepared a garlicky dish for her date. While her culinary skills may not have been top-notch, the two shared a great connection. Perhaps her date appreciated the effort she put into the meal, regardless of the outcome.
Only some people are natural-born chefs. Some people possess innate kitchen talents, while others may struggle to create a masterpiece. However, this story demonstrates that a fantastic connection can sometimes outweigh a less-than-stellar meal. Despite what might have been one of the worst dishes he’s ever had, the couple still embarked on a second date, proving that there’s more to a relationship than culinary prowess.
#7: Family Ties
It’s safe to say that discovering you’re related to your date is an incredibly awkward and unwelcome surprise. In this case, the silver lining was that the two found they were third cousins early in the date before things could progress further. This revelation undoubtedly saved them from an even more uncomfortable situation.
Strangely, these third cousins, who appear to be around the same age and live in the same city, had never met. Perhaps they crossed paths at a family event without realizing their connection. Regardless, the discovery allowed them to avert a potential disaster and move on from an unforgettable date.
#8: Unconventional Workplace
On a date, one of the first questions people typically ask is about their partner’s profession. Many individuals want to date someone with an exciting or interesting job, while others may emphasize their partner’s career less. Regardless, certain domains might raise eyebrows or even be potential deal-breakers.
For example, dating a funeral director might seem daunting due to the nature of their work. It can be challenging to ask about their day when the subject might be uncomfortable. In such cases, it’s wise to avoid bringing a date to the office, especially on a first date, to prevent unnecessary discomfort.
#9: Love Conquers
This heartwarming story truly showcases the power of love. A woman went on a date while taking ulcer medication, which unfortunately caused her stomach to make unpleasant noises and triggered bowel movements. Despite the embarrassing situation, the date seemingly went well, as the couple eventually married.
The fact that this man wasn’t deterred by her temporary digestive issues speaks volumes about their connection. Their ability to enjoy a pleasant first date, even with the awkward side effects of her medication, suggests that their love was meant to be. Sometimes, the most unexpected and challenging situations help solidify essential relationships.
#10: Dining Disappointment
Dating through apps like Tinder can be a hit-or-miss experience, and users are typically aware of the risks involved. It’s no secret that some peculiar individuals lurk on dating apps, and one can only hope not to encounter them during a date.
In this instance, the woman’s date took her to Hooters and flirted with the waitress, which was already questionable. But to make matters worse, he was also on the phone the entire time. While a first date at Hooters might be okay if both parties are in on the joke and can laugh about it, this situation was disappointing.
#11: Sushi Surprise
Sometimes, unfamiliar situations can lead to humorous misunderstandings. In this story, a woman went on a first date at a sushi restaurant, which was a new experience for her. Unfamiliar with sushi, she mistakenly ordered 13 rolls, thinking it meant 13 individual pieces.
A sushi roll usually consists of eight pieces, so her order was far more extensive than expected. One can’t help but wonder why her date didn’t correct her when she placed the order. Perhaps he thought she was hungry and didn’t want to offend her? Regardless, this lighthearted mishap is a reminder that first dates can be filled with amusing and memorable moments.
#12: Lost in the Pre-Cellphone Age
The pre-cellphone era presented unique challenges for dating. On the one hand, people can handle constant connectivity and the added pressure of social media. On the other hand, simple conveniences like quickly contacting your date were unavailable.
Take, for example, Todd’s story. When he arrived at the wrong address for his date, he couldn’t just pick up his phone and ask for the correct location. Instead, he spent the evening with a kind elderly couple, searching a phone book to find the valid address. This amusing anecdote highlights the stark difference between dating experiences in the past and the present.
#13: Dodging the Kiss
People have different expectations and boundaries when it comes to first dates. For some, a goodnight kiss is off the table to avoid appearing too eager or desperate. In this case, a woman wanted to ensure her date wouldn’t attempt a goodnight kiss at night’s end.
She sprinkled her pizza with garlic powder to deter him, ensuring her breath would be less inviting. When her date gave her a quizzical look, she candidly admitted her intentions. It’s interesting to wonder how the rest of their date unfolded, but this story serves as a reminder that honest communication can often make things smoother in the dating world.
#14: Unexpected Ending
This story certainly keeps you guessing until the end. As the narrator describes their date concluding at the ex-wife’s house to help her choose a wedding dress, the ex-couple might be reconciling. But, as it turns out, the ex-wife was preparing for her wedding to someone else.
This surprising twist raises many questions: Why did the date lead to the ex-wife’s house? What was the guy’s involvement in this situation? And why did the protagonist go along with it? Regardless of the unanswered questions, it serves as a reminder that dating can be full of unexpected turns.
#15: Age Mix-Up
Miscommunication can lead to awkward dating situations, as seen in this story. The protagonist thought they were going on a date with a girl they had met, but she had a different idea. Instead, she believed she was setting her grandmother up on a date with the narrator.
This scenario prompts some questions: How much younger was the girl? If she thought the protagonist was a suitable age for her grandmother, there must have been a significant age gap. The story highlights the importance of clear communication and understanding each other’s expectations before venturing into the dating world.
#16: Unexpected Guests
It’s hard to determine which part of this story is more off-putting: the 25-year-old guy bringing his parents on his date or his mother asking the protagonist if she had finished her meal to take home the leftovers. Taking a doggy bag after a date is acceptable when there’s a lot of food left, but having your mother do it for you is another matter entirely.
Bringing parents along on a date is certainly unusual, especially for adults. While it may be common for young children to go on their first-ever date, it’s not something you’d expect from a grown-up. This situation would likely make anyone reconsider a second date, regardless of how great the person may be otherwise.
#17: In Need of Approval
This story features a man who didn’t bring his parents on the date but called his mother to request permission to watch an R-rated movie. While close relationships with parents can be commendable, it’s understandable why the protagonist opted not to pursue a second date.
One of the perks of adulthood is the freedom to make decisions, like watching R-rated movies, without parental approval. So, when a 21-year-old ends a date because his mother doesn’t allow him to watch a particular film, it comes across as peculiar.
#18: Nervous Charm
Feeling nervous while talking to someone you’re attracted to is entirely natural and happens to the best of us. Some people may overthink every word, while others might blurt out the first thing that comes to mind. It seems that’s precisely what happened to this woman, as she responded without much thought.
Nevertheless, her reply is quite endearing. When told, “You smell good,” she responded, “Thanks, I use both my nostrils.” This shows a woman with a sense of humor! Though we don’t know the outcome of this date, it appears to be more manageable than some of the other stories shared. There’s a high likelihood that they laughed off the awkward moment.
#19: Parking Woes
Parallel parking can be challenging for some people, including the guy in this story. He asked his date to wait outside while he parked the car. However, after three unsuccessful attempts, he gave up and drove away, leaving his date stranded on the curb. Her date night was ruined, and she also had to walk home. Fortunately, she lived nearby!
After the parking debacle, the guy was likely too embarrassed to face his date. Moreover, the entire situation could dampen anyone’s mood for a date. He probably realized he couldn’t park the car and decided to avoid further humiliation by driving off instead.
#20: An Unfortunate Spill
Accidents happen, and if the girl in this story had a good sense of humor, she might have found the situation amusing. Nonetheless, no one wants to show up at their date’s door with a suspicious stain on their pants. Hopefully, Patrick was charming enough to make up for the mishap.
While it’s not the ideal way to start a date, things could have been worse, as evidenced by other stories on this list. First impressions matter, but they can be altered. If Patrick is a decent guy, there’s a chance the girl could look past the not-pee stain, and they share a lovely evening.
#21: The Power of Second Chances in Dating
We all make mistakes, and sometimes people deserve a second chance. It’s a beautiful sentiment that can lead to forgiveness, growth, and even the formation of strong relationships. However, sometimes giving someone a second chance can also lead to disappointment. One woman shared her story of giving a guy a second chance, only to discover that he was a disappointment. While this experience may have been discouraging, it’s important to remember that not everyone will be a good fit for us, even if we give them a second chance. It’s important to keep an open mind and heart, but also to have boundaries and self-respect.
In the end, the woman in the story didn’t have a second date with this guy, and it turned out that he might have ended up in prison. While it’s unfortunate, it’s also a reminder that sometimes things don’t work out for a reason. It’s important to trust our instincts and not settle for less than we deserve in a relationship.
#22: Overprotective Family
This story evokes sympathy for the girl who is so sheltered and shy that she struggles to date and interact with strangers. We can’t pinpoint the reason for her fear, but we hope she receives the help she needs to overcome it.
Nevertheless, dating someone and spending the evening with their sister must be odd. While the woman likely had good intentions and was trying to support her younger sibling, she may have inadvertently caused more harm than good. But, surprisingly, the couple still managed to schedule a second date!
#23: A Cringe-worthy Approach
Feeling insecure on a date is natural, as it’s a situation where you know someone across from you is evaluating you. Some individuals attempt to boost their confidence by discussing their exes, boasting about their past relationships, and their former partners’ attractiveness.
It seems that’s what this guy aimed to do by showing his date pictures of his ex-girlfriends. But why did the photos need to be explicit? Was he trying to prove that he dated beautiful women? Regardless, this cringe-worthy tactic likely backfired, and it’s safe to assume they didn’t plan a second date.
#24: A Deceptive Encounter
This story undoubtedly ranks high on the list of awkward first dates. It’s hard not to lose faith in humanity when faced with such a situation. How would you react if this happened to you?
The issue with this story is different from the unconventional proposal itself, as people have varying preferences and interests. The problem lies in the man’s dishonesty towards the woman. He never disclosed his marital status or true intentions, leading her to believe they were embarking on a specific date for the two of them.
#25: Disappointing Reality
The opening sentence might lead us to believe this person met their future spouse at 14, but sadly, that’s not the case. Instead, this story reminds us of the unfortunate reality of school bullies. Many of us have faced bullying while growing up, and some might have even been bullies themselves.
This relatable tale is undoubtedly a bitter memory for the person involved. These kinds of experiences tend to linger in our minds. Hopefully, he was too good for the bully and eventually found someone special to share his life with.
#26: Miscommunication Mishap
It’s essential to ensure that both parties know they’re going on a date and have similar expectations. In this story, the woman thought she was joining a group of friends to watch a Vikings game. Little did she know, the guy had planned a romantic one-on-one evening at a five-star restaurant.
Assuming she would cheer on her team, she donned her Vikings jersey and painted her face to show her enthusiasm. Imagine her surprise when she entered the fancy restaurant and realized the misunderstanding. It’s genuinely baffling how such a significant miscommunication could occur.
#27: Unwanted Encounter
There’s nothing wrong with opting for a casual restaurant for a date. Only some first dates need to be at a high-end, upscale establishment. Some people prefer a local coffee shop or chain restaurant to create a more relaxed atmosphere and alleviate some pressure.
However, this story involves a unique Applebee location where the guy’s ex-wife works. Of all the people you’d prefer not to see on a date, your date’s ex-spouse would likely top the list. He must have known she worked there, yet he chose that specific location. It’s hard to believe this was merely a coincidence.
#28: Brutal Honesty
People don’t always want to face the truth; sometimes, they’d rather be deceived and live in an illusion, especially when the truth might be painful. However, in this case, the guy opted for brutal honesty, which turned out surprisingly well.
At the night’s end, his date thanked him for dinner and a movie, to which he responded, “Yeah, I didn’t have anything better to do.” While such a comment might put some off, this girl found it hilarious. Fast forward three years, and they’re happily married!
#29: Unexpected Surprise
Navigating high school dating can be challenging. Even when we may not be ready, there’s immense peer pressure to be in a relationship. Add to that the awkwardness of puberty and self-discovery, and high school dates can be pretty uncomfortable.
One person shares an engaging high school date story. Already nervous, they felt something strange with their sweater, causing them to fidget and scratch their back. Eventually, they reached up their sleeve and pulled out a pair of their mom’s panties! Unfortunately, we don’t know how the story ended, but there’s a good chance the date found the situation amusing!
#30: First Date and Red Flags
During a first date, many potential warning signs can arise. For instance, when your date admits to having no money and asks to borrow a small amount, that’s a red flag. When your return from a convenience store with a scratch-off lottery ticket, that’s another warning sign. So much went wrong even before I had a chance to suggest going to a strip club.
It begs the question of how she even decided to go on a date with him. Did he seem perfectly normal before this evening? Indeed, she must have had some prior interaction with him. While we’re not blaming her, it’s worth considering why she chose to go out with him in the first place.
#31: Love and Dating Apps
In this digital age, we have new ways of connecting with loved ones and meeting new people. The advent of dating apps has made it easier for individuals to find their ideal partner, and many have found their soulmates through these platforms. There is no shame in using dating apps to find love.
If you’re currently in the market for a relationship, you may be familiar with Tinder and other similar dating apps. While meeting the love of your life through these apps is possible, there is also a chance of encountering some peculiar individuals. Unfortunately, Emily experiences the latter in this case. Following this unfortunate incident, it’s understandable if she takes a break from Tinder.
#32: First Date Surprises
While some people may enjoy surprises, it’s essential to consider if surprising your date is appropriate, especially on a first date when there’s a lot at stake. It may be better to be upfront and avoid leaving anything to chance. After all, mistakes can be learned from and avoided in the future.
For example, Jimmy Fallon once surprised his date by taking her to the restaurant where she worked. However, this surprise may not have been appreciated as the first date was spent at her place of work, surrounded by her colleagues and boss. It’s a reminder that not all surprises are good ones.
#33: Clashing Beliefs
It’s ideal for sharing similar values with your partner, even if you don’t always think alike. However, it cannot be accessible to date someone who doesn’t share your values regarding essential matters, like diet or animal rights.
One individual found out the hard way when his vegan date and her friends organized a protest against sushi at the sushi restaurant they had chosen for dinner. He had unknowingly found himself on a date with a vegan, and while it made for a funny story, it’s a reminder of the importance of being aware of your date’s values and beliefs.
#34: When Love Hurts
Stubbing your toe on a table or nightstand can be one of the most painful experiences, leaving you limping for weeks if not months. It’s something other than what you want to happen on a first date or any additional time.
One unfortunate girl experienced this when she stubbed her toe walking into the bar. Despite the pain, she decided to continue with the date, only to discover halfway through that her injury was worse than she had initially thought. Her shoe had filled with blood, and her night ended in the emergency room. However, she could get a second date at least, so the night wasn’t a disaster.
#35: Managing Expectations
Finding a partner, you feel comfortable talking to as equals is essential, where neither person feels inferior or superior to the other. However, only some have exact expectations regarding a partner’s intelligence.
One Twitter user was on a date with a guy who seemed intimidated by her intelligence. Halfway through the date, he revealed, “I wasn’t expecting you to be intelligent.” This remark highlights the importance of managing expectations and knowing what you’re walking into when dating.
#36: The Big Brother Theory
Conspiracy theories have been around for as long as we can remember, and the idea of Big Brother, where the government is constantly monitoring our every move, has persisted over time. Sometimes, it seems like a distant concept, while it feels more relevant at other times than ever.
One woman was on a date with a man who wrapped his phone in tape because he believed the government was always listening. It must have been tedious for him to constantly wrap and unwrap his phone whenever he needed to use it. This shows that the fear of being watched is still alive and well in today’s society.
#37: Parental Involvement
It’s surprising how many adults still think bringing their parents along on dates is acceptable. This seems to be a recurring theme in some of the stories we hear. In one case, it’s unclear whether the woman knew her dad would be there. However, the fact that she kept giving secret glances throughout the night suggests that she knew he would be there.
Whatever the case may be, it’s safe to say that this date did not end well, and there was likely no second date. Establishing boundaries and keeping parental involvement to a minimum in romantic relationships is essential.
#38: Breaking Gender Stereotypes
In the past, men were known to open doors, send flowers, and perform other chivalrous acts for women. While some argue that chivalry is dead, there are still men who act in this manner. However, not all women want to be treated in this way. They prefer to be treated equally to men.
One woman took this to heart on her date and walked ahead of her partner, quickly getting into the car first so that he wouldn’t have the opportunity to open (or not open) the car door for her. Unfortunately, she got into the wrong car and only realized her mistake when her date pointed it out. Although it may have been embarrassing then, it made for an excellent story to tell on the Jimmy Fallon challenge!
#39: The Friend Zone
While kissing or hugging your date at the night’s end is customary, a high five can signify being put in the friend zone. It’s not a romantic gesture and conveys that you’re not interested in a romantic relationship.
This could be how the night went for one girl who expected more from her date. However, a high five made it clear that he only wanted to be friends. It may not be the outcome she hoped for, but there needs to be clarity about his intentions.
#40: A Date Gone Wrong
Many things can go wrong on a first date, but perhaps the worst is hitting your date with your car. Unfortunately, that happened to one person on a disastrous first date. While we don’t have any more details about what happened, it’s safe to assume that there was no second date, and the person who got hit with the car didn’t want anything to do with their date after that.
We can only hope that the person who caused the accident took responsibility and helped cover the medical bills. It’s a reminder to always be careful and aware when behind the wheel, especially on a date.
#41: Love at First Sight?
Blind dates can be nerve-wracking, but at least you usually know what your date looks like. However, one woman on a non-blind date realized that she had forgotten what her date looked like. Fortunately, her date had a great sense of humor and decided to play a little prank on her by letting her do a few laps around the restaurant before finally waving at her.
Despite the initial mix-up, the couple hit it off and married. They have a funny first-date story to share with their future children and grandchildren. It’s a reminder that sometimes love can come from unexpected situations and that a good sense of humor can go a long way in making a connection.
#42: The Awkward Date
Some situations are just awkward, and this is one of them. It’s hard to say who should feel more embarrassed in this scenario – the guy using his date as a cover or the unwittingly involved girl. Regardless, it’s not a comfortable situation for anyone interested.
The fact that the waiter felt the need to speak out adds to the discomfort of the situation. It’s a reminder that sometimes we don’t know what’s happening in other people’s lives and should try to avoid making assumptions about their relationships.
#43: A Clumsy Kiss
Sometimes accidents happen, which seems to have occurred in this scenario. The guy accidentally elbowed the girl in the face as he leaned in for a kiss. While it’s not the most romantic ending to date, luckily, the girl could overlook the incident.
It’s good that the rest of the date went well, as the couple married and have been together for twenty years. It’s a reminder that a bit of clumsiness can be overlooked when there’s a genuine connection between two people.
#44: The Sister Rivalry
Sibling rivalry can be challenging, especially when you’re constantly being compared to your siblings. So, when a guy on a first date asks if your sister is single, it can blow your self-esteem. This kind of behavior is unacceptable and can be exceedingly hurtful.
It’s important to remember that we are all unique individuals and should never be compared to our siblings or anyone else. If someone can’t see our worth without comparing us to someone else, they’re not worth our time. This girl was lucky not to go on a second date with this insensitive guy.
#45: The 50-State Mix-Up
It’s easy to get mixed up regarding the number of states in the U.S., After all. There are a lot of them to keep track of! So, when a guy corrected his date’s mistaken belief that there are 52 states instead of 50, it wasn’t necessarily a deal breaker.
The couple is happily married now, which shows that sometimes a little mix-up can lead to a happy ending. It’s important to remember that we all make mistakes, and it’s okay to be corrected and learn from them. Who knows, maybe this mistake led to a conversation that helped spark a connection between the two.
#46: Building a Connection before Meeting the Family
Regarding dating, it’s crucial to establish a connection with your potential partner before bringing family into the mix. First dates should be focused on getting to know each other, not introducing family members. Bringing the family along can be overwhelming and even scare away a potential lover.
One woman had an experience where her date seemed more interested in finding a homemaker or maid than a life partner. It’s essential to take the time to get to know each other and build a connection before considering involving family members in the relationship. Family can be important in a relationship, but the timing and situation should be carefully considered to ensure a successful and comfortable experience for everyone involved.
#47: The Importance of Sharing Food
Sharing food can be an essential aspect of a relationship, but respecting each other’s boundaries is also important. If you don’t like to share food, it’s best to find a partner with the same preference. However, practicing good hygiene at the dining table is crucial whether or not you want to share food.
One woman had an unfortunate experience where her date sneezed into her plate and then proceeded to help himself to her fries. Not only did this turn her off, but it’s also important to remember that in today’s world, good hygiene practices are more critical than ever. So, whether you like to share your food, always cover your mouth when sneezing or coughing at the table. It’s a small but significant gesture that can make a big difference in maintaining a healthy and respectful relationship.
#48: When Pranks Go Too Far on a Date
Do you remember the TV show “Punk’d” hosted by Ashton Kutcher? Well, one woman’s date seemed like it belonged on an episode of that show. The guy asked her to smell his food and then shoved her head into the plate. This juvenile prank might have been funny on TV, but it didn’t impress his date. It’s safe to say that first dates don’t get much weirder than that.
If this prank indicates his sense of humor, it’s no surprise that she decided to ditch him. While humor can be a great way to bond on a date, knowing where to draw the line is essential. No one wants to be the victim of a hurtful or humiliating prank, especially not on a first date.
#49: Moving On to a Higher Calling
After a date, there are few things a guy wants to hear less than “you’ve helped me decide to become a nun.” It’s unclear whether the date was so bad that she’s swearing off men, or perhaps it went so well that nothing can top it. However, it’s more likely that this decision had nothing to do with the date itself.
It’s possible that the woman had already been considering pursuing a religious vocation, and the date helped her solidify her decision. While it may be disappointing for the guy to hear, it’s important to respect her decision and not take it personally. Sometimes, a date can lead to unexpected revelations and life-changing decisions, and that’s okay.
