75 of the most cringy online dating fails that will have you cracking up

I often wonder if old school dating was full of all the angst and horror common to 21st-century dating. Or at least the type of dating that was introduced with services like Tinder.

I’m sure in its own way it was. But it was certainly lacking something we have today. The ability to share all those horror stories by just tapping on an icon. And aren’t we grateful for that?

We’ve collected 75 hilarious fails. Believe me, there are lots more, but we had to stop somewhere. So if you’re looking for some entertainment at someone else’s expense—after all, they had to live through it, not you—settle in and prepare to laugh yourself silly.

1. The cheesy line segue

Tired old pickup lines are tired and old for a reason. Following it up with being a pig really doesn’t help either, as the reply proves.

2. That would be a no

Are you wondering where he was offering to wear the hat? Because I sort of am. Not that it makes any difference, mind you.

3. I threw up a little

You’ve heard that right? I threw up a little in my mouth. I peed a little. These are not positive things. Why does he think “I smiled a little” is?

4. Does he understand the concept of conversation?

Don’t you hate it when someone asks you a question and doesn’t give you time to reply? And then their next question is about your thong? Me too!

5. I’d like to be more productive

One track mind? Did he think he was the answer to her increased productivity?

6. Notice the omission?

Yes, the omission is a reply. Because really, if some stranger asked you that, would you bother to reply? Or are you busy changing your number?

7. Ouch

Guys are so sensitive about this! But he did open himself for the slap down, didn’t he?

8. I’m sorry?

Does this person really expect the recipient of this lovely message would fall for that? Placing the blame on autocorrect? Uh-huh.

9. So, um…

This was an intro message? As in this was the pickup line? Does this work in any known universe?

10. Flame out

I love the fire emojis. Because someone clearly crashed and burned with their pickup line.

11. Nope

First, really? That is so immature. Second, she made her thoughts on the matter clear. Why carry on?

12. You are your avatar

No one is looking to date your truck. So using your truck as your profile pic and not getting it when someone calls you on it… well, I have no more to say.

13. Day of rest?

I know a lot of people take it easy on Sundays, and I’ve been known still be in my PJs at noon, but I probably wouldn’t share that with someone I’m trying to impress. Didn’t seem to stop this guy. And apparently it got him nowhere.

14. Those first impressions

Frankly, I’m completely confused by this. “You o face?” What could he possibly have meant?

15. Is he nervous?

I’d think in a situation like this you would take a moment before hitting send. Right? I think he lost his chance.

16. A conversationalist

Look at the depth of this conversation spread over 3 days. However, despite the lack of words we’ve learned a lot.

17. Soul mates

I’m stretching here, but I guess someone’s profile indicates they are sarcastic. Which absolutely means you should hook up with someone else who is, right? Wrong!

18. Seriously?

Is this guy for real? He tells her she’s kinda ugly then continues his madness. And I’m sorry, but she should have stopped right there.

19. Don’t walk, run

I guess I have to give the guy props for being honest up front, but please! If someone has to go through that much to see you, why are you on Tinder?

20. Sure, the other guy did it

But you already did try to recover. You tried to blame the fact you are a jerk on someone else. And she is clearly out of your league.

21. Froze him out

And he was smart enough to realize it. And yet stupid enough to do what he did.

22. Hahaha

If you are going to use technology for this kind of thing, make sure you know how it works. And prepare to get a masterful slap down like this.

23. Um, what?

How old is this person? I should think teachers showering with children would have been against the rules for a long time. Even in Europe.

24. You there?

No, you idiot! You scared her away. You should have left it at 6 foot 8. And she will probably have a nightmare about being chased by a tall goblin with little hands and big feet.

25. It’s so hard to be original

No, wait. It really isn’t. Just be yourself and forget the stupid lines. We get it. There is pressure. But please, pass on the stupid lines.

26. No beating around the bush here

The answer suits the question, doesn’t it? She uses an analogy and he replies in the same vein. Clearly a clever guy.

27. Is she confused?

She’s not looking for a date or something a bit more long term with a guy. She’s looking for a temporary place to live. Try Kijiji or the want ads.

28. Where’s the intrigue?

That’s what she feels is missing? I’d say there was a whole lot more missing, but then I’m pretty picky about what I expect from a guy. Especially one who has never met me.

29. She’s my hero

Is there something in her profile that suggests she might be flattered by this question? Regardless, I love the slap down.

30. Was she being sarcastic?

I really don’t know. Isn’t there a chance she was honestly complementing him? If she was, oopsie!

31. That can’t be for real

Can it? Is there such a major, and if so why would anyone take it? It’s not going to lead to job success, and someone is clearly going to need job success for that debt!

32. Just stop, already

Was the long drawn out explanation necessary? Hey, sorry. I think saying I just met someone and it’s going great would have been enough.

33. Say what?

Perhaps this person doesn’t clearly understand the purpose of Tinder? I’ll admit to never using it myself, but even I know it’s not the place to go looking for a dad.

34. Stuck in a rut

Perhaps this is the limit of their English? What other reason could there be for asking the same thing over and over again? Other than the fact you are an idiot, of course.

35. Alex is clearly a dick

What do you cook? Unless someone has shared their culinary expertise with you, this is not a question you ask a woman.

36. Clear goals

They both seem to have clear goals, right? It’s also clear that those goals don’t mesh at all.

37. What a winner

What does it matter if he can’t tell which one is her? Apparently he doesn’t like the look of her or her friends. But at least he got his love of turtles in there. I’m sure that took the sting out of his insults.

38. I am seriously LOL

Alex, Alex, Alex. I get that you’re trying to impress the girl. Any maybe some girls would be impressed. But you might not want to lead with the fact that you’ve never read a book before. Just sayin’.

39. Dear swipe left

I have one question for you. You are short, aren’t you? Okay, two questions. Is everything in proportion on your short little body. Thought so. Not interested. That would be the only way to deal with this, am I right?

40. Real question or questionable grammar?

How are you sexy? Or how are you, sexy? Hard to know, right? Either way, I don’t think she was impressed.

41. Honestly!

Is this guy a good representation of what Tinder has to offer? And he actually thinks she would let him near her dog if she had one?

42. Move on, honey.

I say move on because he clearly has. I mean really, nine days and she still hasn’t caught a clue?

43. Bitter, much?

What an awesome way to introduce yourself to someone. Everyone loves to be characterized by sweeping generalizations based on your sad past.

44. Someone educate this guy

Does he really think that was trying? I see zero effort here, so he got back exactly what he deserved. A big fat nothing.

45. Yep. He’s going to be alone for life

Is he using dancing as an analogy? I don’t know, but it doesn’t really matter. He thinks way too much of himself.

46. Seriously?

This is just frightening on so many levels. What kind of guy lets his mother check his Tinder? What kind of mother does this? I bet Jordan never heard from this girl.

47. That’s a little heavy

Heavy on the verbiage and heavy on the intent. They haven’t met yet but he seems quite comfortable about laying down the rules of what he would like to see happen next.

48. So lame

Okay, I get there is a list of Tinder pickup lines. But please. This is just lame, and he deserved to get shot down, in my opinion.

49. Sister wives?

So someone has already managed to find one fiancée on Tinder. Yay for them. But they’re still looking for another. Just… wrong.

50. Mirroring

Someone probably thinks they are being clever. They are not. However, the response is pure brilliance!

51. Question, answer

It’s really such a simple process. Someone asks you a question and you answer it. Asking another question is annoying, especially when you’re being a pig.

52. You’d think he’d catch a clue

It starts off okay. An interchange of civil conversation. When it takes a turn for the worse, she gives him fair warning. Did he not understand or not care?

53. Why, just why?

What is with these guys? Suddenly a decent conversation takes a turn for the worse.

54. Nice. What a prince.

He’s probably not in sales. Because if he was, he would know better than to point out that he’s a loser.

55. Hmm, let’s see

He can’t spell. He mentions her age. He doesn’t hear anything from her for a week and tries again. I think he had his answer already, don’t you?

56. So he’s a fake

This is a good thing to know. There’s a good chance he’s dishonest in a whole lot of ways.

57. Could we know his real name?

Assuming he’s telling the truth, wouldn’t you love to out this guy? He’s charging people hundreds of dollars of hour and has no respect for them. He should be disbarred.

58. Huh?

Okay, he’s into polka dots. He thinks retro women are sexy. And I get what he’s saying otherwise, but is he speaking in these choppy sentences because he’s having a seizure or something?

59. Oh, nice

A man of few words? He thinks this is sexy? He never learned how to form actual words into sentences? It doesn’t seem to matter, because she clearly didn’t care to find out.

60. What a catch!

Someone is impressed with himself. And I think he did a fine job of detailing all of his best qualities don’t you? She thought so too.

61. I may be wrong, but…

I sort of get the impression he isn’t interested in conversation. At all. Not even to get what he clearly wants.

62. He means play cards, right?

Play a board game. Watch some Netflix. He can’t possibly think telling her he likes her dress is enough to get what he wants, can he?

63. What?

Maybe English isn’t his first language? Why is he apparently confused by her question?

64. He demands your attention

What was poor Briony thinking? 16 minutes have passed, and she hasn’t replied. He seems a little controlling, don’t you think?

65. Guys can be so stupid

This seems to be going fairly well. They are having a conversation and clearly understanding each other. Then he has to point out she’s older than him. What is the big hang-up with a woman’s age?

66. Let’s not be harsh

I guess a little credit where credit is due should be given. If you look at the dates on this it did take about 9 months before he made his move. So there is that.

67. I’m confused

Isn’t he supposed to try to impress her somehow? Somehow, I think insulting her job and her character won’t get him far.

68. What a smooth talker

I mean, isn’t this the kind of thing we all want to hear when we ask about someone’s weekend? It’s certainly not the answer I’m looking for.

69. What exactly did he want?

A little rude, don’t you think? We have such extremes here. You ask someone how their weekend is going, and you just never know where it can lead. Scary.

70. Maybe it’s not about the age

So he watched football all day. She did a variety of cool, fun things with friends. Then again, maybe she does sound more grown up than him—not that the football thing makes him immature, of course.

71. Someone needs to educate him

Hasn’t it always been a few dinner dates—maybe even lunch—first? And enough with the emojis! Think of what you are asking for! At least have the decency… Oh. What am I thinking, asking for decency here? I lost my mind for a minute.

72. Does he have a life?

Maybe a job? Does he realize that other people may have a life and or a job? And that just maybe they can’t reply immediately?

73. He needed to ask?

This may be a leap, but I expect calling a woman a cougar—especially when she is only 32—when trying to connect with someone on Tinder is a bad idea. And she really slapped him down, didn’t she?

74. Creepy, much?

Getting in a car with a strange guy and going for a long drive is such a good idea. Especially if you met them on Tinder.

75. Nope, that is lame

This is his introduction? I just got home from work, and I’m gonna shower soon? You’re right, it’s not a pickup line but it is entirely lame.

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How to Fail at Tinder

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