Home Business People Share Truly Horrific Stories Of Their Worst First Dates

People Share Truly Horrific Stories Of Their Worst First Dates

MonicaJuly 26, 2022

Drug Dealer

Some red flags happen to come out on one of your very first dates with someone. Even though it can feel like a letdown, it’s a blessing in disguise. This girl took this Reddit user to her “watering hole,” which is a place where she was too friendly with everyone, and not for good reason.

At first, someone that says hi to everyone seems like a great person to be around. But when that reason has to do with drugs, that’s a reason to run the other way. Unfortunately, this woman left her date to go hop in a car with her cocaine drug dealer. The bartender also had this guy’s back and gave him a beer for free for having to deal with that girl. At least he was warned far in advance (via Reddit).

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Wrong Car

Being an independent woman is something many females strive for, especially in this day and age. It shows confidence and is an attractive quality to have. On one of the first dates with this guy, this woman tried to be independent and make sure her date didn’t open the car door for her.

She walked right up to a vehicle, opened the door, and sat down. Her date ran over to the window and said, “this isn’t my car!” She must have felt so flustered as she tried to get out of the car before the owner came back. It’s better to always make sure you ask your date what type of car they drive, before making any assumptions (via Nature World Today).

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Nervous Or Something

Going on a first date with someone is nerve-wracking. All you want to do is make an impression and not say the wrong thing. Unfortunately, some people can take this a little bit too far on one of their first dates. This guy didn’t want to mess up so badly, that he went so far as to not say anything at all.

Her date was probably nervous since he only spoke to his guy friend. Maybe he didn’t want to say the wrong thing, so instead of attempting to talk, he decided to completely ignore his date. We can feel compassion for him for being nervous, but a little bit of effort is usually expected. Maybe she gave him a second chance and the second date went a lot better (via Reddit).

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Three Husbands

If someone talks dirty on their first date, it can either be a huge turn-on or a turn-off. There’s no way of knowing until it happens to you. Then, and only then, will you realize if you’re into it. This Reddit user shares their experience on two different first dates, both of which seemed like complete fails.

The first one told him to fist her, and the second one had three different husbands, still fully involved in her life. At least he mentioned there was no fisting involved. It seems like a string of bad dating luck for this guy. Hopefully, he found his perfect partner soon after these women (via Reddit).

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Actual Blind Date

This sounds like something from a horror movie. Imagine checking your phone after an incredibly awkward date, only to realize that the person you thought you were eating with wasn’t the right person?

We can’t imagine that moment of shock when the truth hit him. He ate dinner with a total stranger who didn’t say a word the entire time. Was it the girl’s friend and they were playing a cruel joke on him? Or did she just see an empty chair and decided to plop down, in the hopes his actual date wouldn’t show up? We’ll never know, and it seems like this guy will never know, either (via Nature World Today).

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Plunge To Becoming A Nun

There are some people out there who wish to become nuns, monks, or priests. These people turn celibate and do not date. When this guy shared his experience on one of his first failed dates, he mentioned that the girl he was seeing was thinking about becoming a nun. Usually, things like this fester for years before someone makes an actual decision.

By the end of the date, the woman decided to become a nun. He helped her make that decision. Something must have clicked for her during the date because, by the end of it, she made a life-changing decision. We’ll never know what went on in her head, but it seems like her date made the wrong impression (via Nature World Today).

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The Winnings

Why would you go to a strip club on one of your first dates with someone? It’s so wrong. Not only did this guy borrow $10 from Chelsea, but he used it to buy a scratch-off, then won $60, and then proceeded to ask if his date would join him at the strip club.

This guy seems plain creepy. There are some things you do on a first date and other things you don’t do. This guy seems incredibly obnoxious, and she’s better off dating someone else. The best Chelsea can do at this point is to say good riddance. She deserves to be taken out on a date to a nice restaurant, not a strip club (via Nature World Today).

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Bloody Toe

Getting injured is never fun. If it happens, we always hope it won’t be during an embarrassing moment, like one of our first dates with someone. On Alida’s first date, she stubbed her toe as she walked into the bar. She didn’t realize her entire shoe had filled with blood, and once she did, she had to make a trip to the emergency room.

At least it seems like she’s dating a decent guy because she got a second date with him. He didn’t mind her clumsiness and might’ve even found it cute. It’s a great story to tell, and it turned out for the best. It could’ve been worse, she could’ve never seen the guy again (via Nature World Today).

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Are We On A Double Date?

There are some things you just need to keep to yourself. When two guys sat next to this girl and her friend at the movie theater, she leaned over to her friend and asked if they were on a double date. She was joking and was making light of the situation. Maybe she was hoping they would turn to her and say, “yes.”

It completely failed and turned out to be one of those nonexistent first dates. The two guys would have laughed along with her, but, nope. That silence that followed her comment must’ve been incredibly awkward and deafening. What’s even worse is that you can’t walk away in a movie theater. Your next best option is to change seats, which these two guys did. Still, they had to sit in the same room as them for the next couple hours (via Nature World Today).

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Meant To Be

Honestly, this could’ve turned into a beautiful love story. A woman gets a traffic ticket, and then ends up meeting the cop again, and the two of them fall in love. It’s like it’s meant to be. For some reason, they saw each other a second time.

Unfortunately, Linda was in a bad mood after getting the traffic ticket. To make matters worse, the person she was on a blind date with was the cop who gave her a ticket. She didn’t see the humor or beauty in it, and instead, felt like it was one of those first dates that are a major fail. It’s possible that the cop had a fun time on his date with her and decided to revoke the ticket. Now that would make everything worth it (via Nature World Today).

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Final Regret

When you’re out on a date, it’s always a good idea to put your phone away. That way, you can be fully present with your date and not have to worry about anything else going on. It’s one of the best ways to figure out if you like someone or not.

This guy decided to not only text his best friend on his first date, but he also proceeded to tell his best friend that he regretted asking the girl out. It turns out that he accidentally texted his date that message. We can only imagine the awkward, heavy silence that followed that text message. There’s nothing much to say after that except goodbye (via Nature World Today).

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Found Out We Were Third Cousins

There are some things in life that you hope will never happen to you. Dating your third cousin is one of them. Thankfully, the odds of that happening are slim, but it does happen. On one of this person’s first dates, they found out they were about to go on a date with their third cousin.

Honestly, it’s better late than never. If the two had fallen in love, there could’ve been a lot of problems. If they had found out after they had kids, there’d be even more problems. It’s better it happened this way and not any other way, although it’s still unfortunate that it happened at all. They’re probably going to be a bit more cautious about who they date from now on (via Nature World Today).

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Mario Kart

Going on one of your first dates ever can feel scary. You’ve put in a position where you have to entertain the opposite sex and make sure they’re having a good time. It’s especially true if you’re a man, since, by societal standards, you must court the girl and treat her to a nice evening.

No one taught this guy how to court a girl on a first date. Instead of taking her out, he decided to serve her saltine crackers and play Mario Kart with her. Even though that sounds like a fun night, it’s not something you usually do on your first date with someone. On the other hand, it could’ve been one of the best first dates ever. It all depends on who you end up with (via Nature World Today).

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Always Listening

Dating someone who’s extra paranoid isn’t ideal. When dating a conspiracy theorist, things can feel interesting for a while, but after some time, it can get pretty annoying. On one of Klara’s first dates, she discovered her date’s phone was taped up.

Without hesitation or making any assumptions, she decided to ask him right then and there why his phone was completely taped. He told her the government is always listening. Even though that’s a bit creepy, at least he was honest. He allowed her to decide whether to stay with him or not. It’s likely she didn’t stay with him. Everything about that conversation is certainly suspicious (via Nature World Today).

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Low Expectations

Setting low expectations for a date makes it a lot easier for them to leave room for an impression. This guy set low expectations for his date. He didn’t expect her to be intelligent. When she was able to hold a conversation about religion and humanity, he was blown away.

Maybe he never dated an intelligent woman, so he didn’t expect her to be one. Either way, kudos to her for surprising him. Still, it doesn’t seem like he’s worthy of a date, since she had to work her way to get him to have a conversation with her. Honestly, she needs to date someone as open as she is, not someone who doesn’t think she’s smart enough to hold a conversation (via Nature World Today).

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Ranch Dressing Kiss

Trying to kiss someone with a mouthful of Ranch dressing is usually something that happens later on in the relationship. That’s when you’re so comfortable with someone, that you don’t feel a need to impress them anymore.

When it happens on a first date, it’s a little different. You don’t know the person at all and don’t even know if you’re attracted to them. Bennett had to endure his date leaning in for a romantic kiss, with a mouthful of dressing. That’s just nasty. No one wants to taste someone’s chewed-up ranch dressing. Still, it could’ve been an honest mistake, or she was just trying to be funny. At least she wasn’t pretending to be someone she’s not (via Nature World Today).

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Elbow To The Face

You’d think that getting elbowed in the face would turn you off of a date. It almost seems like a warning sign from the universe, saying, “don’t date this person.” It’s a hilarious story that could’ve ended horribly. Surely, it seems like a disaster and is one of those first dates that make you grateful for your simple, yet boring dates.

It ended up working out for this guy, since not only did he get a second date, but he ended up marrying the girl. It’s a cute love story, and because it worked out, it’s one of the best ways to start a romance (via Nature World Today).

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A Clockwork Orange

When a date is going well, it’s hard to know when to say goodnight. After this Reddit user had one of those wonderful first dates that make us believe in love, it went south. His date asked him if he’d ever seen A Clockwork Orange, to which he said he hadn’t.

Without hesitation, the girl suggested they watch the movie. After watching the gruesome movie, the girl was in the mood for some “sloppy toppy.” He was not. His mind was full of horrible images. Maybe she’s into BDSM and felt turned on after watching the movie. That’s a person to reconsider (via Reddit).

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Bring The Mother

When you go on a date, you don’t expect them to bring their mother. That’s something that happens months into the relationship after you’ve set a solid foundation and like each other. For some reason, this person thought it was a good idea to bring their mother along on one of their very first dates.

It could’ve been a cute evening, but this person thought it was incredibly awkward. We’re not sure we’d want our parents on any of our first dates, or any of our dates, ever, but this person did it without hesitation. At least he knows she and her mother have a good relationship (via Reddit).

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Pre-Cellphone Era

Todd mistakenly didn’t ask his first date for the correct address. If this happened nowadays, it wouldn’t matter since something like that could be fixed with a quick phone call. Unfortunately, this happened before cell phones were a thing, so Todd had to go the difficult route and ask a friendly neighbor to help him find his date.

He must’ve gone to the wrong house because the elderly couple made him watch TGIF while they searched for a phone book. That’s one way to kill some time while you wait. It’s a funny story to tell on one of your first dates, though. Let’s hope she was understanding and found the whole thing hilarious (via Nature World Today).

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He Gave Up

Parallel parking is stressful. If you have a bad temper, it can make it even worse. This guy was a big jerk and left his date stranded on the side of the road after he couldn’t parallel park. Instead of trying to find another parking spot, he drove off and left her there. Maybe he was so embarrassed that he didn’t want to face it.

Because of this, she had to walk home alone. That’s not a great way to spend one of your first dates with someone. As we’ve said many times before, it’s better to happen on the first date instead of months into the relationship (via Nature World Today).

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Catch Me If You Can

There are some people out there who leave impressions, and others who don’t. This guy certainly didn’t leave an impression on this woman, since she forgot what he looked like. After she walked around the entire restaurant looking for him, he finally flagged her down.

The best part is that he allowed her to walk around and look for him. He sat there, thoroughly amused, as she wandered around the restaurant, lost and confused. Even though that’s harsh, it’s quite a hilarious way to start the first date. At least it ended in a beautiful romance, and the two of them ended up getting married (via Nature World Today).

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