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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

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
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.

i guess im just a play date to you 

the audio on tiktok where 12-29 year olds dance in slow motion like Timothée Chalamet

*plays play date by melanie martinez*
girl 1: omg this is the best part!
girl 2: omg yessss
*dances in slow motion*