Bored Panda
67 Top-Tier Date Fails That Hurt To Read But Are Hilarious
Funny,FailsFEB 16, 2026

67 Top-Tier Date Fails That Hurt To Read But Are Hilarious

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Anyone who is currently dating knows how difficult and confusing the process can be. On the one hand, you’re excited to meet new people! On the other hand, some of those people turn out to be so cringy, creepy, or clingy that you can’t wait to vent about them.
Bored Panda has curated this list of the biggest dating disasters and awkward fails to show you just how bad things can get. Scroll down to check out these people’s stories, but be warned, some of them come with a big side-order of secondhand embarrassment. It’s enough to make you glad that you’re already in a relationship or to swear off dating altogether.

#1

67 Top-Tier Date Fails That Hurt To Read But Are Hilarious
69points

#2 That's Wild

That's Wild
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51points

#3 This Waiter Is My Hero

This Waiter Is My Hero
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50points

What you (think you) know about dating, successful relationships, and ‘perfect’ partners might just be wrong.

Based on the findings of a study published in the Proceedings of the National Academy of Sciences, your own judgment of your relationship reveals more about its quality and success than your or your significant other’s personality.

#4 Who Only Eats One Slice?

Who Only Eats One Slice?
47points

#5 The Bro Code Kicked In

The Bro Code Kicked In
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46points

#6 And That's How I Met Your Mother

And That's How I Met Your Mother
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40points

In a nutshell, how appreciative you are of your partner, and how satisfied you feel your partner is with you, are more important than who you both are as individuals.

The vital things are the effort you both put in, your commitment, appreciation, satisfaction with your intimate life, perceived satisfaction, and how you handle conflict.

So, instead of obsessing over whether your significant other checks all or most of your boxes, you should focus on engaging with them.

#7 Cool Ok Bye

Cool Ok Bye
40points

#8 This Is Actually Hilarious

This Is Actually Hilarious
39points

#9 Had To Pay To Give Legal Advice

Had To Pay To Give Legal Advice
39points

“When it comes to a satisfying relationship, the partnership you build is more important than the partner you pick,” the study’s lead author and an assistant professor at Western University in London, Ontario, Samantha Joel, told CNN.

“It seems to me that the relationship is more than the sum of its parts. It’s that relationship dynamic itself, rather than the individuals who make up the relationship, that seems to be most important for relationship quality.”

#10

67 Top-Tier Date Fails That Hurt To Read But Are Hilarious
38points

#11 Suggested A Date, Got A Lecture

Suggested A Date, Got A Lecture
37points

#12

67 Top-Tier Date Fails That Hurt To Read But Are Hilarious
Report
34points

Many people try to come across as better than they really are on first dates. It’s natural. Most of us want to leave a positive first impression on the strangers we meet.

And yet, this means that you might not get to grips with someone’s real character, quirks, and flaws until much later into dating them, because they’re actively trying to hide them.

#13 He Started Crying

He Started Crying
34points

#14 Happy Ending

Happy Ending
33points

#15 At Least You Realized Before It Got Too Far

At Least You Realized Before It Got Too Far
32points

Luckily, some people are so awful at leaving good first impressions that you can instantly recognize their red flags and problematic behavior patterns.

Though this leads to awkward and embarrassing encounters, this is actually a good thing. Why? Because you instantly realize these individuals are worth avoiding. And so, you won’t waste any more of your precious time dating them.

#16 Like How Does That Happen

Like How Does That Happen
31points

#17 Mistakes Were Made

Mistakes Were Made
30points

#18 People Do Weird Things

People Do Weird Things
29points

The Guardian notes that some of the worst things people can do to leave a bad impression on a first date include things like arriving late, canceling the date on short notice, or even not bothering to turn up with no warning.

Other things that might push your potential partner away are things like looking wildly different from your dating profile photo, complaining a lot, and whining about being exhausted.

#19 Man Found Exactly What He Wanted. Talking Stage Is Not Necessary

Man Found Exactly What He Wanted. Talking Stage Is Not Necessary
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29points

#20 Not The Paper

Not The Paper
29points
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