30+ Text Messages That Are Too Cringy To Read But Are Still Somehow So Entertaining
They range from plain uncomfortable to straight-up creepy.
Some text messages are so awkward, so over-the-top, or so badly timed that they become entertaining in a whole new way. That is exactly the kind of chaos this collection leans into, with screenshots that capture everything from strange flirting to painfully awkward roleplay.
Across these examples, people are texting friends, partners, and strangers, and the results are messy in the funniest possible way. A few messages are just weird, some are unintentionally hilarious, and others are so cringy they practically demand to be shared.
By the end, it is hard to tell what is worse, the messages themselves or the confidence behind them. Read on.
1. Got Caught Watching P*rn
VortexThing2. Please End The Asterisks Roleplay
eggofreddo3. Better Not Skip The Next Months Ahead
drukqsx
4. Phone Hack Prank—Or Does This Even Count As A Prank?
NateM135
5. Again With The Asterisks
reddit.com
Some people really commit to the bit, even when nobody asked them to.
6. Oh, He Has The Ego
sumitxt
7. This Is So Gross
FreudianCeline
8. Don't Be All Sensitive
WengerBaller
9. You Need Space, I Gave It
10. Who Wants To Be With Someone Who Starts A Conversation With This? Honestly
reddit.com
That opening line did not exactly set the mood.
11. Weird Role Play Thing
reddit.com
12. What Kind Of Asterisk Roleplay Variation Is This?
SpaceAbduction
13. Roleplaying With Crocs
thacarter72
14. "I Showed My Girlfriend This Sub, And She Hates It So Much, So Occasionally I Mess With Her"
bcoltharp
15. "Miley Cyrus’ Brother DMed Somebody In My Insta Feed Because She Commented 'Gross' On A Pic He Posted Of Himself Choking His Fiancé"
reddit.com
At this point, the screenshots are doing all the talking.
It’s giving the same kind of tension as the friend who flirted with your partner, and you wondered if you were overreacting.
16. What The Hell, No
Pixel871
17. "He's Been Begging For Weeks To Do A 'Sexy Roleplay' With Me. I Finally Said Yes. I Think He Regrets Everything Now"
TheOwlAndTheFinch
18. A Furry Obsession
reddit.com
19. "I Love My Best Friend, But She May Watch A Little Too Much TV..."
ambvi
20. Except Hannah, Poor You
MysticStryker
21. Allergic To Guacamole And You, Especially
DemonsGunnar
22. *Shoots Self Right In The Eye*
io7hazcookiez
That is one way to make a conversation instantly unforgettable.
23. Maybe He's Looking For Fanfic Inspiration
requiemsword
24. None Of Them Seriously Took Off
scottmichaelscott
25. Is This How Greetings Are Done Now?
reddit.com
26. Umm, No Comment
hatt730
27. Don't They Have Any Tactics Left?
LRFE
28. This Is Why Chelsie Doesn't Like You
warkmash
29. It Ain't Cute
elcatundo
30. Sorry, Wrong Person
Eklypto__
31. I'm A Microwave
reddit.com
32. Again With The Asterisks
je_suis_un_negre
33. Oops, Sliding Out...
Tanno
34. What The Hell Is This...And On Tinder, Too?
HoDub
35. The Perfect Response
Spider_Dimwit
Honestly, what is it with all these asterisks and role-playing? It works for some people, but for the general public, not so much!
Have you ever encountered someone who sent cringy text messages like these? Comment down your thoughts and experiences or share this article for all your family and friends to see!
May your inbox stay far away from this kind of chaos.
Want more awkward texting fallout? Read how “dating advice” to a friend’s crush led to a breakup in this friend-group disaster.
