thats cool I guess 

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.....

thats cool I guess by Cambria S January 14, 2008

That's Cool I guess 

Something that people say to almost anything that is in no way cool/they used no guesswork in any way, shape or form.

Oh well that's cool I guess.

That's Cool I guess by The Homie Himself 💯 May 13, 2011

I guess that's cool 

1)When you are trying to do something in a game. Ususally a bad outcome resulting in being pancaked or hit and run in UT3 or being impact hammered while trying to shock combo.

2)When someone screws you over.

Oh, i just got ran over by the scavanger. I guess that's cool.

Paul: You went to taco bell and didnt tell me? I guess that's cool.
John: I didnt know you were here!

I guess that's cool by John Erwin June 20, 2008