guess this pretty much proves girls don't know what they want. but hey its not your fault.
girls seem to like it better when guys are just a little mean to them, make fun of them, etc etc.
it really comes natural to guys, but what happens is some guys tend to get confused and think girls will absolutely despise them for it, if they say anything slightly bad or mean to them, even playfully.....because well girls always moan and groan how guys are dicks, or jerks, so we don't know what you want 99 percent of the time.
maybe tell him to be a little more playful and meaner. although i don't think its his personality.