Lyric discussion by flayerhater 

Cover art for Win lyrics by David Bowie

I guess I'll take a stab at this one...

I think it's about sexual negotiation.

"Since you're trying not to lose Since I'm not supposed to grin"

It's like Bowie knows she's attracted to him, but he can't show it, so he has to slow down, and play the "game" a bit more first.

"slow down, let someone love you"