well it's certainly doable, if unlikely
by the way, the chances of being able to win AND have sex with sexy girls is the PRODUCT of the chances of each. so, if
chances of winning = .02 (or 2 percent)
chances of having sex with sexy girls (non-hookers) = .15 (or 15 percent)
then the chances of
winning AND having sex with sexy girls (non-hookers) = .02 x .15 = .003 (or one-third of 1 percent)
if they are correlated, the chances of both happening increases from .003
If they are anti-correlated, as I strongly suspect they are, the chances of both decreases even lower than .003
if you include hookers into these equations, the numbers change, of course