Let’s face it — dating is tough. For every love story out there, there are at least a few dates that have gone horribly wrong. After all, you have to kiss a few frogs before you find your prince/princess, right? Well, these dates went so poorly that even the internet is cringing! See the worst first dates of all time, and then try to resist the urge to delete all of your dating apps.
Different Isn’t Always Better
It appears that this poor guy got caught in the middle of his date’s mid-relationship crisis. She seemed to believe that the grass was greener on the other side, but one dinner with this dude convinced her that her ex was the best there is!
While we feel sorry for the OP, we can’t help but be suckers for this love story which he most certainly is not the star of.
He Was Playing the Game
This guy must have some serious, well… balls. While that’s some expert-level playboy-ing, we can’t help but wonder why he didn’t simply schedule the dates for different days?
The only reason we can think of is that he didn’t want to be tied down to one woman even for an afternoon. Now, that’s a level of commitment-phobia that we’ve never seen before. That being said, we’re in awe of the confidence in which this guy made up his own rules for the dating game.
Have All the Desserts
Honestly, this woman should have 10 desserts! One for every pound she “should lose.” Not only do we have no doubt that she’s perfectly beautiful but we’d like to see how this guy looks, considering how he thinks he’s one to talk. Something tells us that his self-esteem isn’t too high, which probably answers that question.
We hope there won’t be a next time but if there is, this girl should order at least two desserts — one for eating and one for throwing in his face.
Thanks for the Life Hack
This woman is living in 2088 while we’re all still stuck in 2022. Her life hack for getting out of a bad date is simply genius and we’ll be using this in the future. After all, time is money, so she can easily “earn” back what she tipped that waiter by ending the night early.
We’d like to add to this woman’s brilliant idea — when going on a first date, make sure to wear something you don’t mind “accidentally” spilling a drink on.
Keeping it in the Family
This one is both equally gross and unfortunate. It kind of makes sense they’d connect, though, doesn’t it? As it turns out, those two had way more in common than they’d ever hoped!
We’re just glad that they figured it out before things went even further than kissing… family reunions are awkward enough as it is. Although, clearly, they could do with a bit more of those since they can’t even recognize their own family!
It’s Too Late for That
We would not be scared if someone’s tooth fell into our mouths while kissing — we’d be absolutely terrified. Is that some sort of sadistic version of pillow talk?!
We guess it was kind of polite of him to warn her, rather than let her get a nasty surprise, but maybe he shouldn’t have gone in for a kiss at all till he got that issue sorted. We give him an A for manners but an F in planning ahead.
Worst Third-Wheel Ever
This is one of those rare instances in which both parties can probably agree that it was the worst first date either of them ever had. At least mom seemed to enjoy herself!
While she’s certainly no matchmaker, this mother does seem to be incredibly wholesome and she obviously looks out for her daughter, so it’s difficult to get too upset. Maybe the dating world just isn’t ready for adorable moms like this one, yet.
Who Is His Ex?
Ah, the troubles of dating in Hollywood. A person can’t really get over a relationship when their ex is famous and always in the media.
That being said, intentionally going to see a movie she is in was completely that guy’s bad. Taking his date to the movie? We really have no words. If he was trying to show off the fact that he dated a beautiful actress, we think it’s safe to say that plan backfired.
Why Is That, Though?
We do sincerely feel bad for this man but we can’t help but wonder why that date with him turned out to be this woman’s last date for a while. What did he do to turn her off from relationships entirely?
Clearly, he’s unaware of whatever faux pas took place, so we assume that he’s a good guy who meant well but maybe his date’s side of the story is somewhere on this list…
Talk About Planning Ahead
Most of us want to know where we stand with the person we’re dating and we appreciate it when that individual wears their heart on their sleeve. However, many people also want someone who’s mysterious and sparks their curiosity.
It can be difficult to balance these two contradictions and sometimes, a person can accidentally tip the scale too far in one direction. Or in this guy’s case, just reject the scale harder than Leonardo DiCaprio rejects women his own age.
She’s a Fast Learner
To be fair, this woman has done exactly what was asked of her. Her date wanted her to say “please” more often and that’s the very word she used to get away from him. We truly can’t say that we blame her.
This guy’s strategy of trying to mansplain manners to a grown woman isn’t exactly the best way to score a second date… or even get through the entirety of a first one.
He Dodged a Bullet
This guy may just be the luckiest man alive. Not only did he drive through that snowstorm safely but he also dodged a huge bullet by getting rejected by his date.
We do understand this woman’s belief that her date was being inconsiderate by arriving late but she could have asked him why he wasn’t on time before deciding to leave. Oh well, given the dedication that guy put into even showing up at all, it’s safe to say that it’s her loss.
This Is Just Too Cute
This one hits a bit different knowing that they got married in the end — it’s actually an adorable first date story. Sure, it’s a bit embarrassing, but this woman clearly found her wife’s manic-pixie-girl energy to be endearing more than anything.
It just goes to show that no matter how quirky someone is, there are always those who will love them for it. Let’s just hope that this woman knows what her wifey looks like now!
That’s Her Villain Origin Story
Every villain has an origin story — something that pushed them over the edge to become the antagonist they are today. Well, this date appears to be that woman’s story and we really can’t blame her for the cynical dater she’s become.
If everyone had to endure a date with this guy, it’d simply be a world full of anarchy. We bet he’s one of those guys who wonders why he attracts “crazy” women, not realizing that he’s what’s making them crazy.
Nan Was Probably Angry
Imagine being a perfectly happy spirit, doing ghost-like things, and then suddenly being summoned to witness a horrific first date. We’d be annoyed, to say the least.
Watching our grandson blow his chances of getting a girlfriend wouldn’t really be our first choice of how to spend the afterlife. We have no idea why he would choose a date to speak to his deceased grandmother but he’s probably earned himself a lifetime of getting haunted because of it.
A Meet-Cute Gone Wrong
This story could have made for a really good meet-cute but, unfortunately, it just wasn’t meant to be. Romantic comedies would have us believe that this initial hatred towards each other would fuel this couple’s eventual romantic passion and then everyone in the restaurant would spontaneously burst into song.
Unfortunately, this interaction simply ended in an extremely awkward evening and maybe some leverage if this guy tries to give the OP another ticket in the future.
Accidentally Running a Charity
It appears that this poor guy ran an accidental charity! Well, there are a lot worse things in life than unintentionally doing a good deed. Here’s the thing — how did this woman know to sit with him for a free meal?
Our theory is that it was, in fact, the woman he was meant to be on a date with and she just wanted a nice dinner without needing to make small talk, so she sent that text after the fact.
There Are Places for That
Here’s what makes interactions like this confusing — there are those who work in an industry in which a customer can pay for intimacy. So why wouldn’t someone just go to one of those places, rather than take a person out on a date, if they just want to exchange money for physical favors?
Ironically, that woman may have been planning to kiss her date before he asked that question. Now, he’ll most definitely be going home alone and he’s out a decent amount of money.
We’re All Confused Here
Something tells us that everyone meant well here but literally, not one person had a clue what was going on. Clearly, the couple on the date was confused and each thought that perhaps the other knew the elderly couple.
Meanwhile, we can only assume that the elderly couple also thought that they knew these youngsters, somehow. We take this as a hilarious misunderstanding rather than anyone having ill intent. Even better, it’s a great story that both pairs can tell for years to come!
Well, It’s Not All Bad
This has got to be the most creative way ever that someone’s gotten a client. While we don’t approve of the deceitfulness, we have to admire this guy’s work ethic!
Before feeling too bad for this woman, let’s keep in mind that a cute date is a dime a dozen but a decent mortgage rate is a lot harder to come by! We’d say this woman can consider that evening to be a huge win.
It’s a Solo Date
Clearly, this guy wanted to see that specific movie more than he wanted to spend time with his date. Well, at least he knows his priorities! As far as bad dates go, this one really isn’t the worst.
The woman still got to see a movie and didn’t have to spend too much time with a guy it wasn’t going to work out with. It’s actually a pretty good strategy for a person who doesn’t want to be rude and leave a date early but they’re not having fun.
Not Enough Said
We disagree that enough was said here… we have a lot of questions and concerns. To be fair, this seems like an honest mistake to make but we can definitely see how it’d be a serious mood killer.
As long as this guy helped his date heal and stayed with her in the hospital (if needed) we’d say he deserves a second chance. Maybe she should do the driving on the next date, though…
That’s a Morbid Third-Wheel
We’ve heard some pretty bad third-wheel stories but this one has got to be the worst. We appreciate that this guy is desensitized and doesn’t notice anything strange about having a body in the car but he should really try to understand his date’s perspective.
Taking one’s work home with them is always frowned upon, but in this case, it should be straight-up illegal! We hope this guy’s next date will be a gothic woman who will appreciate her man’s dedication to his morbid work.
That’s Technically Not Cheating
We’re not really sure how we would react here. It’s technically not cheating if he’s trying to cheat on his date with… his date. Or is it? At least she can rest easy knowing that this guy truly does think she’s the most beautiful woman in the room.
He should probably work on drinking a bit less, though. A person doesn’t make that kind of mistake from just a couple of drinks and a trip to the bathroom.
How Not to Handle Rejection
This guy needs some serious lessons in how to handle rejection because he simply proved this woman right in not wanting him. Here’s the thing — men who get a lot of women don’t need to brag about how they have a lot of women.
We have no doubt that this woman feels she dodged a bullet. Had this guy responded in an appropriate manner, she may have even regretted her decision. Instead, he’s moving on to “the next one” a.k.a. his hand.
Um, a Little Help Here?
We completely appreciate this woman’s desire to be a strong and independent individual. That being said, she may have been a bit overeager here. There’s nothing wrong with letting a guy be a gentleman every now and then.
We hate to say it but it seems that this woman deserved her moment of embarrassment. Maybe next time, just let the guy do his thing? She can always simply tell him that she doesn’t like chivalry, that’d certainly be less awkward.
Don’t Drink and Text, Folks
Ah, the dangers of drinking and texting… one could easily end up sending the wrong message to the wrong person. Really, though — why was this guy texting while on a date anyway? We’re sure that the date he regretted was a perfectly nice guy.
After all, he still gave him a ride home after being insulted, didn’t he? We certainly wouldn’t do the same. Chances are, after posting this, the OP will have no problem finding plenty of dates.
Well, if He Was Hungry…
How was this guy unable to wait even just a few more minutes until the date actually started? The woman was early, after all! The one thing we’ll say in this guy’s favor is that he certainly knows what he wants and is a go-getter who marches to the beat of his own drum.
Unfortunately, he might be just a little too independent for this woman. Oh well, better luck to her for next time!
So… Is She?
He can’t have actually thought this would work out in his favor? Now, he’s lost both women. We feel like he’s seen one too many Mary-Kate and Ashley movies from the early 2000s, where they’re constantly swapping places on dates and stuff.
Dear random guy — if those sisters were to swap places on a date with you, they wouldn’t be fighting over who gets to stay. They’d be fighting over who gets to throw a drink at his face and storm out.
Who’s Really the Victim Here?
Something tells us that the OP isn’t the real victim here. How much younger is “a little younger” to him? Our bet is that he’s really closer in age to the grandma and was trying to creep on a much younger woman.
The fact that this girl didn’t even fathom he could be hitting on her kind of tells us that she’s nowhere near his age range. This is some perfect karma right here.
Four Reasons Why She Left
We’d like to counteract this list by making our own list explaining the four reasons why this woman likely left her date in the middle. 1) He’s superficial, evidenced by the items on his list. 2) He’s arrogant and just assumes that she’s interested in him.
3) He’s organized enough to make a list but not organized enough to be on time. 4) He’s giving some serious small, um, “package” energy. See? We can make lists, too.
If it Ain’t Broke…
We understand this woman being offended but we don’t actually think her date was that bad. What’s wrong with playing the field a bit? She can’t really expect loyalty and commitment from this guy before they even go on a first date!
That being said, he should really diversify and not take all of his dates to the same restaurant. We get that he probably has the logic of “if it ain’t broke, don’t fix it” but, clearly, it’s broken.
It’s Official: Chivalry Is Dead
We’re all for gender equality but let’s settle this debate of who should pay on the first date, here and now! Men get to walk down the street without fear of being harassed. They get equal pay in the workplace. They also get bodily autonomy, without the government’s involvement.
What do women get? A free dinner when on a first date. We’re sure that the women of the world would gladly trade and let the guys have the free dinner if we get all the other stuff.
Nobody’s Perfect, Especially Not Him
Was this supposed to be a compliment? We argue that she’s still too good for him, given his desire to list her flaws. Unfortunately, this just highlights his own flaws and insecurities. We hope that this woman’s response was to list all of his flaws for him. That’s only fair, after all.
Then she should have said, “You were right, I am too good for you,” done a hair toss, and walked away. We would have slow clapped her out of there.
Those Must Be Fascinating Sheep
This guy is clearly very niche and needs to find someone who has the same interests as him. There’s nothing wrong with having unique interests but maybe he should try to find his Little Bo Beep instead of wasting time looking for Cinderella.
It’s a bit cruel but we think, given what a terrible time this woman was having, she should have ordered the lamb for dinner. Just to see how he’d react…
Norma Bates, Is That You?
We would leave this date straightaway. Not even because this guy, inexplicably, brought his mother along. More importantly, he treated his mom like a dog and had her wait in the car.
We hope that, at the very least, he cracked a window for the poor woman. Was he at least planning to bring her some food?! We’re getting some serious Norma and Norman Bates vibes here, which means that it’s most definitely time to go.
That Probably Wasn’t Tea
Okay, seriously, what was in that tea? His poor girlfriend probably wasn’t expecting that from just an innocent daytime tea outing! We bet the Brits would be proud, given that this guy has combined two of their favorite things — tea and getting wasted.
We hope that guy’s girlfriend broke up with him after that. We also hope that the girl from the next table refused to go out with him afterward. After all, we all know how a date with that guy goes…
