What you say when someone tells you something he thinks is hilarious but really isn't. You say this to avoid hurting your friend's feelings in breaking it to him that his joke sucks.
Dudeman 1: "Oh man, I was playing horseshoes in Red Dead Redemption and I got a really close throw and John was all like, 'Did you see that!' It was so funny dude!"

Dudeman 2: "I guess you had to be there."

Dudeman 1: :(
by Izzy del Bosque June 9, 2010
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A half-hearted yes, or simply agreeing with someone for the sake of responding.
Victor: If you say "I mean I guess," one more time, I swear I'll stop talking to you.
Kaylee: I mean I guess.
by Ultimate Salty Kitty Cunt March 28, 2016
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When someone is proven to be wrong/stupid/lying, but you'll entertain them anyway.
You know we didn't sleep together, but go off I guess.
by Scratch 'N Sniff Asshole March 4, 2021
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1. Thats cool I guess we're best friends so well, awkward.
2. Thats cool I guess I like you but it isnt often people say that to me.
3. Thats cool I guess I'm not paying attention.

Etc. Etc.
Katie: well I like you.
Jaden: thats cool I guess.....
by Cambria S January 10, 2008
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Some mind-blowing last words, said by Ronnie McNutt on Facebook live before pointing a rifle (not a shotgun, it was a rifle) to his chin and shooting himself, literally blowing out his mind.
Ronnie McNutt: Hey guys, I guess that's it.
*Ringtone Noises*
*BANG*
*More Ringtone Noises*
by DrBrad July 16, 2023
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