Fuck, I realize now prostitution is broken so it doesnt make sense. In the next version there is only 1 general sex skill and once that gets high enough mafia lady approaches. In the current version 3 sex skills have to reach level 2 or 3 for her to approach.
My bad, I should have fixed prostitution next update. Instead of random, we have a certain order for the events now so it runs smoothly. Once your sex skill reaches level 3 in the new update mafia lady approaches you, for now it's kinda fucked.