The Absolute Worst Dating Fails You’ll Ever Hear

It is hard to find someone who likes dating. And if you enjoy dating, it is probably because you haven’t been on a bad date yet (and you should thank your lucky stars for that!) Bad dates range from painfully awkward to outright humiliating. We have compiled a list of the worst date fails here. You can either be happy that you haven’t experienced these, or you can relate to them all of their shameful glory.

Bad Manners

There’s nothing like going on a date with someone who has bad manners—especially towards the waitstaff. The snapping and demeaning behavior can be horribly embarrassing. Who wants to be associated with that? No one! Especially when you sit down and your date starts snapping his fingers in the air.

Mistreating your waiter or waitress is rude no-no number one. “My date said, ‘Do I look like the kind of guy who waits for [expletive]? Bring us a couple of martinis.’ I told the waiter that only 1 drink would be necessary and asked my date if I looked like the kind of girl who dates [expletive]. Then I got up and left.”

Committing a Crime

OK—when you hit it off with someone, and the date is going well, you don’t expect to that person drug you. Yeah—apparently that’s a thing! This girl recounts her experience during a date that was going really well (or so she thought).

She was on a date with a guy she had met at Starbucks. They clicked, so they continued the date at a bar. When she went to the bathroom she noticed something not right while she walked back to her date; she saw him slip something into her drink. In a smart move, she pretended to take a sip, but when he wasn’t looking, switched glasses with him. 5 minutes later he was passed out. This is a scary story!

Sick or Cheating?

This poor girl was in a relationship when she experienced the worst date of her life. And when you are in a relationship with someone, you expect to be treated with respect but that is not always the case.

This girl’s boyfriend took her out to an amazing restaurant but kept getting up to go to the bathroom. Here is her recount of the situation: “I felt so badly because I thought he was sick. Turns out he had another date in the back of the restaurant and kept switching between me and her.” That must have felt like a movie- those things shouldn’t happen in real life!

She’s a Runner

When your date is over, you usually want to walk your date to the door, decide on another time to meet up and maybe even share a good night kiss. This poor guy thought all is well that ends well. But this date, at its end, didn’t go well.

They had good conversation and things seemed to be going fine during dinner. Then he offered to walk his date home and she accepted. But you should hear his recounting of the situation since that fateful moment: “as soon as we started walking she sped up and jogged away from me. She never looked back and I watched her get into a cab on the next block.”

Blind Date that Everyone is Watching

If you have been on a blind date, then you know how intense the whole experience can be. You don’t know who this person is, or much about them, and you are probably worried the whole time that the blind date was a mistake. OK, to be fair, some blind dates work out—and others—don’t. Some are very apparently awkward and uncomfortable enough that other people can’t help but notice.

“Recently, I was on a blind date that was so bad that the women sitting at the table next to us actually leaned over and told us both that we should quit while we were ahead.”

Heroic Mess

Most men would jump at the opportunity to look like the good guy and score some date points. This unfortunate guy saw his opportunity and decided to jump into action but got hit by something else in the process. One word to sum it up: ouch.

They were sitting at an outdoor cafe in the city when a gust of wind blew his date’s sweater off the back of her chair; trying to impress her, he jumped up and into action. He chased it into the street. He picked the sweater up and was feeling like a hero – well, until a cab turned the corner hit him.


Like we said, some dates are going seemingly well until the very end. So even if you are having a wonderful time, don’t start planning your future together until a few dates or even until after date one has completely ended. You never know, your date might all of a sudden be homeless.

She met this guy at a bar and they totally connected. They made dinner plans and dinner was great; they really hit it off. He invited her back to his place and that is when things took a turn for the worst: “…when we got there, all his stuff was on the sidewalk…he had been evicted while we were out!! Totally awkward.”

Frodo? Is that You?

If you are a lot like most people who overthink their actions on a date, you probably rehash all the things you discussed and said. Some things you could end up over-analyzing and really aren’t that big of a deal, while other things are much more obvious and you know it once the words leave your mouth. This guy knew right when he said it.

One time, this guy took out this girl who reminded him so much of Elijah Wood from Lord of the Rings that he apparently had to say something. “I shouldn’t have said anything. I don’t think there is a woman alive who wants to be told that they resemble a male hobbit.”

And Now, Kenny

Similar to a blind date are the infamous friend set-up dates. Friends have good intentions but sometimes don’t seem to know what you would want in a potential partner. Which is strange since they are your friend. Well, all we can say is, are you a fan of South Park? Maybe you should look this guy up.

This girl went out to dinner with a guy by being set up by a friend. “He was wearing a hoodie and had the hood up with the strings tied pretty tightly the entire meal. I felt like I was on a date with Kenny from South Park.”

Mommy Dearest

When you ask most single people what they want in a partner, it usually ranges from a variety of qualities. They want someone who is funny—they have to have a good sense of humor. Or they have to be a “family man.” Or they have to be kind and enjoy good, thoughtful conversations. Most people find career goals to be very important. When this guy asked his date what she wanted to be, well, at least she was very honest.

“On a first date I asked a girl what she did for a living and she said that she was waiting to be a stay-at-home mom.”

Just a Minor Detail

Sometimes, dates can seem so chaotic and you don’t know why, which in it of itself can be a bad sign. Well, this girl knew why and it was still a bad sign.

She met a guy for brunch. He was already seated when she arrived, so the host took her to the booth where he was sitting, which was near a few rowdy kids sitting the booth behind them. The kids kept on peeking over the back of her date’s bench and then she realized something. “This went on for about 15 min. before he turned around & yelled at them. Turns out they were his kids! His ex was supposed to watch them, but cancelled.”

Dating for Two

When you take someone on a date, your intention is to get to know them; learn their interests and if they jive with your personality. Maybe you want to see what they want for the future and if your relationship goals align. Well, this poor guy got right to the goal line before the race even started.

Could you imagine asking your date for their wine preference and hearing something you did not expect? This guy was out with a girl and he asked if she liked white wine or red, because he was going to order a bottle with dinner. She said it didn’t matter because she wasn’t allowed to drink until after the baby was born. Total “WTF” moment!

Beliefs and Other Unmentionables

There are many pieces of dating advice that inevitably float around and some will always ring true. How does that saying go? It is something like, you shouldn’t talk about religion or politics on your first date. Never. Never ever. Another solid piece of advice is you shouldn’t talk about your “past” life on your date—it may just give your date a strange feeling about the whole thing. Like, maybe this person is a little too out there.

“One girl I went out with told me that she is a vegetarian because she feels that she was an antelope in her past life. No joke.”

I’ll Take That to Go

The most common date is to take someone to a restaurant for a meal—hey, it’s an oldie but an obvious goodie. You can eat, have a good conversation and potentially continue on from there if the connection is right. You can go get drinks or catch a late movie if you want the date to continue. Or your date may just want the good meal, like this guy discovered on his date.

“I took one girl out to dinner (on me) and towards the end of the meal she asked the waiter to bring her an extra filet mignon wrapped to go.”


When you go on a date, you can’t help but have some expectations for how it is going to go. Most people think that a goodnight kiss and planning to see each other again is a good start, while other people have x-rated expectations.

This woman went out on a date with a guy she had been friends with for 2 weeks. After the dinner and movie, he parked in front of a motel: “I asked him what he was doing, and he literally said, ‘I talked to you, listened to you, and took you out on a date. So you’re gonna [expletive] me right?’”

Follow Your Instincts

So many people rely on online dating nowadays to meet people but it is safe to also say that you don’t really know what you are getting until you see them. That was definitely the case for this very strange encounter.

What would you think if you met a guy from a dating site who wouldn’t give me his last name or number? Or said to meet him “3 hrs after sunset” at a “high vantage point” in a park? Well, if those red flags wouldn’t deter you, you would figure out the end to this story: “Against my better judgement, I went, wandered in the park for 45 min before finding a man wearing a mask. He said he thought it would be a more interesting story to tell my friends. Oh, it was.”

Jumping to Conclusions

You never know what you are going to face while out on your date. Your date can be embarrassing but there are also chances that you may feel embarrassed yourself. Like assuming something is for you when it really isn’t.

He took his date to a fancy dinner. When the check came he put down his credit card but a few minutes later, the waiter returned with scissors & cut the card in half. “I was just about to punch his smug little face when the manager came rushing over. The declined card belonged to the guy at the next table.”

Jumping to Conclusions (Again)

Just like how you may not know what you are going to face on your date, you may also feel like you could get burned. It is hard to trust someone you don’t know that well and that can ruin a perfectly good romantic connection.

What if the guy you had been dating for about a month told you that he was going out of town on business? But you saw him the next night walking into a restaurant with his arm around another girl? Here’s how that situation went: “I was really mad, so I ran over and started yelling at him. It turned out that the girl was his sister and his flight out was leaving the next morning.”

Too Much Talking

Men can often think they know what women want; from what they want to hear, to how they want to be treated in the bedroom, men think they know it all. But sorry guys—it is safe to say you don’t know it all. And you should probably just take it a step at a time and stop stepping on your own toes.

“My boyfriend and I have been dating for about a month. We had sex for the first time the other night. Right in the heat of the moment, he looks me in the eye and says ‘You ready for some [expletive]?’”

The Klepto

And finally, this kind of goes without even saying but we have to say it: When you date someone, you don’t expect them to slowly steal your stuff. That’s a deal breaker. This guy dated a girl for a month when he started inviting her to stay over. Then, he couldn’t find his glasses the next day; then the next time he went nuts looking for his watch. Then it was his cell phone. He thought he was losing his mind, until…

“One night I insisted we go back to her apt. I found all of my stuff in her underwear drawer while she was in the bathroom. When I confronted her she said I was overreacting.”