my thoughts on the game issue:
play your best when you play, doing otherwise is asking for trouble re respect etc
if he really cares about losing some games, then don't play the games where that matters
if it works with both of you, then choose games (e.g. go) where handicapping can actually work
do other cool shit together
i'm guessing he acknowledges/is aware that you're better at these things, and he's better at other things?

I occasionally play some games with my gf where i have a huge edge. We are both aware of this. And it's fun anyway, but only cos she doesn't mind losing too much, but absolutely froths over the occasional win she gets

three cents