I'd say Miami if you don't mind spending some $$$
I agree with Prague being the best place. Ideal Bachelor party location, plenty of things to do, mainly (and probably only) drinking at low prices. Not to mention some interesting clubs they have there.
"Hi. How are you?"
"Hi. I love your ____." I actually talked to a lady for 15 minutes the other day because I complimented her nail polish.
Realistically, with people and pools the ice is usually not very thick.
Just jump in.