cool with it 

To describe someone who would be okay with or who has a tendency to be okay with something (an activity, etc.) that may typically not be condoned by that person's demographic

"Yo, you think I can finish my lunch in Ms. Wong's class though?'
"Oh yeah bro, she's cool with it"

cool with it by Datwhitearab January 23, 2018

be cool with it 

To access a difficult situation in favor of the speaker; to accept the situation at hand. Usually used as an evasive or passive aggressive question when the problem being negotiated is especially awkward.

Hey if I were going to ask your sister out on a date, you'd be cool with it, right?

be cool with it by drnoise June 19, 2010