How do you know he's gay? Was he hitting on you?
On to the actual question:
Over-raising is a bad option. Nix #3.
I think you'd prefer to isolate the short stack, since otherwise you're put in an awkward position on the flop - wedged inbetween live stacks in the blinds and the SS.
How do you know he won't re-raise? I see a lot of short stacks take their shots preflop with small pp's and weaker A's. That possibility, along with the desire to isolate, is making me like a raise of 3-5.
If you were earlier, I would like a very small PF raise (2-3). Then you have a good chance of a couple callers, and by the time it gets to the SS, they see a built pot and might decide to take a stab at it by pushing.
Chris
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