Scenario 1

What happens next is up to you.

Scenario 2

(Again, same pic but with one of my OCs)

Grace: I don't know Qrow. But I will say you look better with your hair down like that. More handsome.

 Grace: Might help you get more simps.

Scenario 3

Again, same pic. But this time you can replace Qrow with your own character and carry out a different conversation.

Pic is found on Pinterest and is actually a part 2 with part 1 showing Ruby styling her hair with his hair gel.