[how_can_losing?]

I think the flop reraise to $40 is a bad idea. He won't fold any slow-played overpairs, and he could have a set or 2p or draw. When he calls your reraise I don't know what he has, but his range probably has great equity vs. your holding. An even bigger problem (maybe) is that you are OOP with nearly half your stack in the pot, and there are something like 27 cards that will make your life difficult.

On the other hand, it seems like folding is out of the question, and a probably is not a good idea. Flat calling isn't that appealing either, but it seems like I would lean toward calling the flop, planning to c/f a lot of turn cards, and maybe b/f some "safe" turns.

I don't play a whole lot of HU cash so take that fwiw.