Yeah it is hip/modern lingo. Ever heard of a kodak moment? Brothers (bro) + kodak = bunch of guys together = bro-dak moment.
I'm not sure how I would proceed in you/Bob's situation. I'd be wary of "mr. cool" looking for revenge if I reported him (would consider it before I do it).
The thing with teh boss feels a little tight too, do you have a good grasp on his personality? If he is one of those against gays I can totally picture him saying something like "well... We'll just let this one slide, next time if he does this, you come back and report to me mmm'kay?"
