I agree, first thing to always consider first is a possible urinary infection, which is very dangerious. SO, watch to see if he goes to the litter box often and tries to go pee and nothing/or very little comes out... followed by a repeat trip to the box etc.
IF that happens, take him to the vet ASAP.
Having said that...
I once had a cat that attempted to urinated on my sleeping boyfriend,(luckily I saw him "squat" and stopped him) and another cat (years later) that urinated in another boyfriend's shoe.
Hindsight being 20/20 both cats were right on in their perception of both boyfriends.
(not to say your boyfriend is questionable)
Neither of mine had an urinary infection... it was some marking their territory thing. (I think anyway)
Good luck to you... I sure know how a behavioral problem is worrisome.