My sister's had a vocation to the street girls (young prostitutes, but she'll talk to and feed the young or old). It's her own thing, except now, the closest parish she has that's "okay" is Maronite, as their formerly-trad parish took a NOSEDIVE a few years ago. (So bad that my sister's family is MOVING to NoVA or Maryland, just to have a possible parish to attend.)
I think that's fine for parishioners to feel a strong calling to help women in danger. I can't do that, but I don't judge the prostitutes or strippers or whoever. And I'm glad someone's doing it, because God Knows the "religious" aren't doing much anymore.
But my sister offers to drive them to Mass too, though. (Maronite, which is a bit harder to understand.) She doesn't exactly cry and "God loves you," but she'll listen to their stories and ask how they might want to improve their lot in life (most have kids), offer help, buy them a sandwich, and invite them to visit Mass to see what God intended for humans. I like the way she's said it (it's from a priest), that whole "the world is fooling everyone, even us, to think this is how God intended us to live...." etc. No cash gifts unless there are hungry children, and my sister knows to look for needle marks, etc signs of drug abuse.
I think the "getting them to Mass" part is really important, though. She says that with her sandwiches: "this is food for your body and your kids, but Church has food for your soul." I think it's pretty cool. We don't have that much prostitution where I live (or if we do, I don't know about it).