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49 Dating Texts So Cringey, You Might Question What Was Going On In The Sender's Head
Funny,FailsSEP 20, 2026

49 Dating Texts So Cringey, You Might Question What Was Going On In The Sender's Head

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Sometimes, online dating almost feels like indulging in the lottery because you never know what you are going to get. Lucky ones might end up with their “happily ever after,” while others might swipe right on people who aren’t even a little embarrassed to show how cringey they really are.
Believe it or not, there are many people whose texts can instantly give you the ick rather than brew romantic feelings. Even if you block them in a jiffy, reading their texts is still a wild ride. The Instagram page Never Stop Swiping has a hilarious collection of these dating messages, so we compiled the best ones for you below!

#21

Cringey dating text about life compared to a deck of cards with a cheesy compliment
9points

Meanwhile, experts argue that this whole rise in cringe culture is not really a good thing. Psychologist Adriana Cardona Rivera explains, “The term ‘cringe’ has evolved into a form of social control that discourages sincerity, risk-taking, and self-expression among Gen Z.”

“The fear of being judged or labeled ‘cringe’ pushes people toward detachment and performance, making genuine connection and personal growth harder to achieve. Reclaiming authenticity means embracing discomfort and being willing to be seen trying,” she adds.

#22

Long romantic dating text describing casual dating and apartment story
8points

#23

Cringey Tinder bio with unrealistic dating expectations and humor
8points

#24

Cringey dating profile text with a self-deprecating joke about heartbreak and intimacy
8points

I guess sometimes it’s okay to be cringey, rather than give in to the whole pressure of sounding cool on dating apps. Don’t you agree? We would love to hear your thoughts in the comments. Also, if you found this list funny, you might want to check out these cringey screenshots that we covered previously!

#25

Hilarious dating negotiation chat about beverages, orgasms, and driving
7points

#26

Cringey dating profile with disturbing message about sleeping together
7points

#27

Funny dating text about fighting cougars and dinner FaceTime invite
7points

#28

Humorous Tinder texts mimicking Alexa with questions and commands
7points

#29

Witty dating text with an unoriginal first date idea about smashing mailboxes with face
7points

#30

Cringey Tinder exchange with a pun about saying grace and having Grace as a meal
6points

#31

Humorous dating message about awkward small talk and Netflix
6points

#32

Cringey pick up line in dating text calling someone a beautiful land mermaid
6points

#33

Funny dating text screenshot about tripping mushrooms and cannibalism
6points

#34

Funny dating text asking to see tires with a photo of a tire
6points

#35

Cringey dating text conversation with playful and awkward messages on Tinder app
5points

#36

Text conversation about living in someone’s socks with a witty response
5points

#37

Dating text with wordplay on the name Destiny mentioning common puns used
4points

#38

Funny dating text comparing someone to Pam from The Office
4points

#39

Cringey dating conversation mimicking duck sounds with suggestive wordplay
4points

#40

Flirty Tinder exchange referencing Bills jerseys and playful replies
4points
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