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It's a phrase that stupid geeks use at the end of each sentence because they don't want to look RUDE, or anything even though they are!
"Hi Mason!"
"Hi....I guess"
I guess by Maryanne E. M. July 9, 2004
Something 11 year old kids obsessed with football say instead of "huh" to try and seem nonchalant when someone says something even remotely abnormal, sometimes even used when someone says a sentence that is completely normal.
Alternatively you could say "I'm really fucking annoying and dry in the way I text" but this works too.
Person A: In depth explanation of something that happens to take more than 1 second to process
Dumbass: I guess bro.
I guess by kArbs... July 6, 2026

I guess you had to be there 

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: :(

I guess she took the kids, huh? 

Use this when you lose custody.
"Hit or miss, I guess she took the kids, huh?"

"Shouldn't have drank too much, I guess she took the kids, huh?"

i guess so

it meant by possibility or probability.

usage : said instead of saying yes
are you ready to leave?
i guess so
i guess so by jibo7399 August 1, 2011

I guess that's it

The last words of Ronald "Ronnie" Merle McNutt, before blowing his brains out live.
Ronnie: Hey guys, I guess that's it.
BANG.