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27 Awkward Text Messages That Are Bound To Make You Cringe

There's a fine line between funny and sad. Pain is funny, but also pain is sad. What is considered funny and what is considered sad will differ from person to person. 

I just bring this up because, man, I really don't know how to feel about this one, guys. Sometimes watching a kid get his heartbroken is funny to me, but other times my hearts breaks, too. It's tempting to say that context is key, but I'm not even sure that is true anymore. Sometimes a cruel person just doesn't know any better and deserves our pity. Other times the nicest person in the world can fail so spectacularly we can't help but laugh.  

So feel how you feel while looking at these text messages. It is all correct.

1. Glad he's okay. That was a close one.
'He was bleed from his mouth' from sadcringe
2. Get it together, Diego!
Oops :-( from sadcringe
3. It's been so long since I last saw you.
Well, at least she cared... from sadcringe
4. Oh, buddy...
Haha yeah from sadcringe
5. How to tell if you are lonely.
"oh i thought you sent that" from sadcringe
6. People are so cruel.
that's gotta hurt... from sadcringe
7. Haha! What a hilarious misunderstanding!
...Ps, I love you (: from sadcringe
8. Par-Tay!
It's not you, it's me
9. That last line is kicker.
My co-worker texted me. (Posting again because I forgot the cringe the first time). from sadcringe
10. You could do nicer.
Idk much about the backstory from sadcringe
11. I don't know. This doesn't seem legit.
At least he tried.... from sadcringe
12. I don't know what else you were expecting.
Hells nah from sadcringe
13. Because you put "Haha" I know you are telling the truth.
My phone was stolen haha from sadcringe
14. Life is so hard!
Poor guy from sadcringe
15. Don't really understand how this is a prank.
Just A Prank from sadcringe
16. Love can be very one sided.
Who is this? from sadcringe
17. Is there anyone else you can talk to?
I wish you were up from sadcringe
18. I agree that the grammar is the most offensive thing here.
Dirty talk from sadcringe
19. Nope!
Poor Tom :( from sadcringe
20. Hannah, do NOT unblock him.
Hannah I'm begging you from sadcringe
21. I love it when you treat me poorly.
"you Cld cheat with my brother...i still wouldnt leave you." from sadcringe
22. You made a lot of mistakes, kid.
oh sorry that was my friend. he was on my computer lol haha
23. The modern equivalent of sending flowers to yourself.
I feel used. from sadcringe
24. Ya blew it!
He used to have a crush on her (x-post /r/tinder) from sadcringe
25. Machine programed to love does not love.
Didn't expect this from Google from sadcringe
26. I mean, I guess that is the right response.
lol aw from sadcringe
27. Never joke about this kind of stuff.
The saddest part about this is that it was me from sadcringe