I'd paint my car that way even if I was 50 lol

Siriously though, Id be kind of creeped out if my boss decided to scope out my place. Although my place is on a main road that most people I work with take to the office lol so it isn't so unusual to have people come up to me and ask "Hey do you live in such and such a place cause I saw your car there" (my car is distinctive too if you know what youre looking for ) I'd leave it alone unless he makes a habit of driving by (kind of keep an eye out for his car on your street) then I'd be taking further action.

Just keep an eye on him, don't really spy but be more alert if ya know what I mean