60 hilarious first date disasters

Dating is hard. There’s so much that goes into finding out if you’re compatible with someone. You have to have the same expectations about where you want your relationship to go. One person might be looking for a serious connection, while the other might be looking to casually break into the dating world again after a divorce. That’s not even to mention the anxiety over the way you look, how easy it is to talk to one another, and so much more.

It’s a long and awkward process and one that most people don’t miss after they’re no longer on the dating scene.

Everyone who’s dated has a couple of awkward stories under their belt. Maybe you spilled wine on your favorite shirt. Maybe your date said something that made it clear from the get-go that it wouldn’t work out. But no matter what you’ve experienced on your worst date, we’re betting it wasn’t anything like these doozies.

These stories include everything from physical injuries to creepy comments to finding out that they were related. If you’re single, these will make you cringe. And if you’re in a relationship, they’ll make you breathe a sigh of relief that you’ve left this all behind.

1. Mystery date

I have so many questions about this one! Did they really eat dinner in complete silence? Who was the mystery girl? How did she know he was expecting someone? What does it all mean?!

2. Well, this was fun

They say first impressions are everything. Unfortunately, these two had the worst first impression possible. Considering how much some traffic tickets cost, I wouldn’t be willing to give him a second date, either.

3. Not all bad dates have sad endings

If there’s anything more embarrassing than choking on a first date, it’s having food fly out of your nose. Happily, for these two, it didn’t spoil the date. They just have an awkward story to tell for the rest of their lives together.

4. The waiter was looking out for her

Not only is this extremely rude, but it’s also inefficient. Did he think that he could get away with it? If you’re going to have two dates, you should probably try to schedule them at different times.

5. Oh, well if your mom said no…

Some people grow up very sheltered. However, at 21, you’re an adult and don’t need your parents’ permission for, well, anything. Also, bear in mind that movies can be rated R for something as simple as one too many swear words.

6. But on the plus side, that’s the best time to find out

This is terrible news to hear, but let’s face it — if there’s any time you have to hear that, the first date is the best time. Obviously, this was a surprise – but life isn’t perfect.

7. This gives a new meaning to the term “third wheel”

Most of us could get behind the idea of dating a funeral director, even if it makes us uncomfortable. But why would anyone ever think this is a good idea? For the love of all that’s good, reschedule the date!

8. A word to the wise: no one has ever wanted this

I can’t believe there is anyone who needs to be told this. In fact, no one ever wants to experience – not men, not women, and probably not dogs. The next time you think of doing a puppy trumpet, just know that everyone hates it.

9. That’s…that’s good, I guess?

The real question is, how much soda did he spill on himself? It must have been quite a bit if he had to lead with that. On the plus side, at least it was soda and not pee.

10. That is definitely not amore

“When the moon hits your eye like a big pizza pie” – you won’t get a second date. Almost no one in the entire world would think this is funny. If you want to make your date laugh, learn some jokes.

11. Could have been a coincidence, but probably not

It’s only natural for parents to want to keep their kids safe. But this crosses a line. If his daughter agreed to the date and felt comfortable, why would he follow them?

12. Well, that was wild from start to finish

This story sure needs some follow-up details. For example, why was he still friends with his ex-wife? Why was she helping her pick out a wedding dress? Why did she ever download Tinder?

13. Now that is…rude

It’s possible to reject someone politely that doesn’t involve insulting them. But that’s not the way this woman works. She prefers to express her disinterest in the rudest way possible.

14. We need the whole story

Wait, wait, wait. Enough hasn’t been said! While we don’t get all the details in this one, we can probably agree that hitting your date with your car is the worst possible move.

15. Can you just take me home now?

At this point, there’s no reason for the date to continue. You’re both embarrassed and no longer want to be there. Let’s just call it a night and wish each other a nice life.

16. The worst time to assert yourself

There’s nothing wrong with opening the door for someone. There’s also nothing wrong with preferring to open the door for yourself. But maybe you should make sure you have the right vehicle before you do.

17. Can you imagine the look on his face?

At first, this probably came across as a terrible excuse for leaving a date early. Luckily “My shoe is full of blood” is pretty easy to verify. At least there was a happy ending!

18. This is terrible on two levels

That’s quite some gall to be so rude to two women at once. Not only was it insulting to the woman he was on a date with, but it was also a slap in the face to his ex-wife.

19. How does one spend that much money at Walgreens?

This is so bizarre that it’s almost impressive. Walgreens is a drugstore that sells basic groceries and toiletries. I’m not even sure how one would rack up such a bill in only 30 minutes.

20. Always terrifying to meet an incel in the wild

There are some pretty weird details in this story, but the main point of it is that he wouldn’t take no for an answer. By the way, dude, if you need to “prove” that you have friends, you probably don’t have friends.

21. This date involves coyotes

Is it worth going on a nighttime hike in uncomfortable shoes just to look at some deer? At best, you’d see them for a moment or two before they ran away. At worst, you’d be pursued by hungry coyotes.

22. Every middle schooler’s worst nightmare

Ah, junior high, when everyone is worried about not looking cool and has nightmares about being naked in public. This get-together combined all of those things to make the worst date of all time!

23. That’s quite the checklist

It’s hard to go wrong with giving your date a polite, personal compliment. This guy managed to do it several times while also insulting short, uneducated women who don’t have his ideal proportions.

24. 10 for gutsiness, 0 for class

There’s a lot to unpack here. Not only was the guy living in his car, but he thought it would be a good idea to take advantage of his date’s shower. Couldn’t he at least have put on some shoes?

25. “I’ve saved the worst for first”

Since Texas can routinely get up to the 110 degrees in the summer, this is quite the power move. But why wouldn’t he turn the air conditioning on? It’s not like he was paying an energy bill in his car.

26. This is the best possible response

Everything about this woman’s reaction is perfect, from her immediate response to her decision to eat pizza. It’s so rude to comment negatively about someone’s appearance, especially on a first date.

27. I was going to eat that

There are a lot of “no’s” in this one. There’s no reason to ever bring your parents on a date, especially if you’re in your mid-20s. As for asking to take someone else’s food home, that’s just bad manners.

28. Just making sure you’re a good Italian boy

This just goes to show that first dates don’t have to be perfect to have a happy ending. And of course, you don’t have to be perfect to have a happy relationship. This lady proved she was a terrible cook from the start — but she still captured his heart.

29. Well… see you later

We’ve all been so embarrassed by something that we turned and walked away. However, that usually doesn’t involve abandoning a date on the curb and forcing her to walk home.

30. You WILL watch TGIF and you WILL like it!

Sometimes, elderly people don’t realize their methods of trying to help are…a little less than helpful. These two were determined to assist in finding this guy’s date, even if it made him uncomfortable.

31. Shh, love is blind

This person established themselves as a jokester right from the start. They were willing to let her walk around in circles, getting more and more flustered until she was forced to admit she couldn’t remember what they looked like!

32. You… you may not

Relationships take time to develop organically. Everyone knows you don’t introduce your kids on the first date. And using someone’s washing machine? That’s long-term relationship stuff!

33. Thanks, I wasn’t expecting you to be a jerk

Some of the people on this list are experts in giving backhanded compliments. This guy was trying to tell her she was smart. But he did it in an unbelievably insulting way.

34. Surely, this tape will help.

Conspiracy theorists live in an alternate reality, believing in some crazy stuff. If he thinks the government is tracking him, he probably also believes the moon landing was fake and the earth is flat.

35. I don’t think you’re doing that right

Here’s another couple that had a terrible first date but managed to recover and go on to have a happy marriage. However, it does make you wonder how he managed to elbow her in the face in the middle of a kiss.

36. That’s the wrong way to recover from that

The simplest way to make sure this doesn’t happen is to cover your mouth when you sneeze. If you don’t have the basic decency to do that, at least offer to buy your date some new food!

37. He’ll hear about that for the next 50 years

“Let me tell you how Grandpa and I met. I was starving and he ate without me!”

“Let me tell you what really happened. Grandma took far too long to get ready!”

38. “You got this right?”

For starters, a girl never wants to pay for a first date. What happened to being wooed and charmed? And to top it all off he wants to know her credit score? NEXT!

39. You people aren’t keeping me from sushi

I can’t help but admire someone who’s willing to sit in the middle of a group of protesters and silently eat sushi. The date may have been terrible, but at least dinner was good.

40. The gang’s all here

This is an unpleasant trick to play on your date without any notice. If you’d rather meet in a group, the least you can do is say that. Don’t just surprise them!

41. We have very different definitions of nice

Sure, Waffle House isn’t a terrible place to go on a third or fourth date — but it’s not first date material. But more than that, Waffle House is as far from “nice” as you can get!

42. You okay in there?

You’re justified in leaving a person you’re on a date with and running if they make you feel uncomfortable or unsafe. But ditching them because you find their conversation boring? That’s such a low blow.

43. This is a total dumpster fire

Don’t go on a first date on Valentine’s Day. If you do, try not to choke on soup. If you own a restaurant, don’t lock your emergency exit. If you think your date is having a seizure, maybe you should help!

44. If only balaclavas were in style

There are few things worse than a bad kisser. As for a bad kisser with too much energy AND a chin full of stubble, that’s an experience you shouldn’t wish on your worst enemy.

45. Those carnival prices are out of control

Sure, food is expensive at fairgrounds, but you won’t need $40 for a couple of tacos unless they’re extra special. How did he expect to get away with that one?

46. Way to go, kiss cam

No one likes kissing cams. They put people on the spot and it’s all too easy to make an awkward mistake — like this one, which ruined the game (and the date) for this unfortunate couple.

47. Do I want to know what a convenience store buffet is?

I want to ask “Why?” but I have the feeling there’s no good answer to most of these questions. What I want to know is: what on earth is a convenience store buffet? The hot dogs on the rollers?

48. It’s a family recipe

Let’s be clear here: there’s nothing wrong with being poor. But if you’re doing this on a date, it doesn’t come across as being poor, more like you’re pulling a skeevy trick to get free food.

49. There’s a fine line between quirky and terrifying

The old trick in middle school was to take a girl to a scary movie so she would cuddle up to you. Unfortunately, it doesn’t work the same way if she’s running through the halls of a haunted lunatic asylum.

50. Oh no

For most people, this would be the shortest date of all time. Just a quick explanation, then everyone decides to forget this ever happened and go home.

51. You couldn’t have just …asked?

Let’s be clear: asking would have also been incredibly rude. But it’s somewhat better than trying to yank someone’s hair off their head. Were you raised in a barn?

52. He made her an accomplice

Considering how hard servers work and how little they get paid; any decent person would be horrified at the thought of doing this. Not only is this tacky, but you’re also destroying someone’s livelihood!

53. There’s a lot to unpack here

If you can’t be bothered to learn your date’s name, why are you even there? What’s more, I have questions about “garbage picking” and the cat statue.

54. Now that we’re…what now?

This woman had some odd ideas about how dating and getting engaged work. In her mind, all it takes is having a meal to know that you’ll be together forever. Poor girl must have been confused when the night was over.

55. Tacky, tacky, tacky!

I’m sorry, but if you sell an MLM product, know that we all hate it. Please stop, we’re begging you. There are few things more insulting than someone feigning interest in you just to sell something.

56. Third time’s the charm

This guy had one thing on his mind, and he was not there for a short-term relationship. Unfortunately, you shouldn’t propose to someone 20 minutes into your first date or a year after not talking to one another.

57. There are no words

You’ve got to wonder what was going on in this guy’s mind. Did he think she would find this interesting? Or that she would be flattered by his ranking system, especially considering that he put her so low on the list?

58. Legend has it she’s still sitting there

This one is so bad it’s almost funny. The girl was so engrossed in whatever she was doing that she didn’t notice him get up and walk away. I would have stayed to see how long it took her to look.

59. Can jumping out of a moving car kill you?

It’s odd enough that he didn’t ask her if she wanted anything to eat, but it’s downright disgusting that he decided to do some dental care right there in the car. PSA: don’t mouthwash in front of your date, and for the love of all that’s good, don’t spit.

60. That’s one way to handle it

Her hashtag makes it clear that they didn’t know one another well, which means she hung out with a broken collarbone at the house of a total stranger for seven hours. Maybe next time you should leave earlier.

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