Those strike as creepy and strategic, like a Hitchcock film, and not funny at all. What am I not seeing here?

I think your humor is being lost in translation. Are you meaning that he is a undeniably evil guy that is trying to be "normal" in those situations? Because currently from what I understood what you have down is that he is so cunning and evil that he will use those situations only when he has no other choice and even then he would use them only as a front to cover his true intent.

Let's take the dating situation, your character would simply abduct the woman who catches his eye and rape her until he realizes that she fears him enough to accept his favor.