Time and trust. Most of LIJ are younger guys who’ve been hurt deeply by women (apart from Evil he’s just emotionally fucked). They’ve been burned deeply and had their hearts battered in some way that makes them hesitant to fully accept women. Someone they’ve fucked is never going to earn that. It would have to be someone who accepts them flaws and all, who doesn’t try to change them, and isn’t trying to land in their beds or win a ring from one of them. It would have to be a woman who isn’t interested in anything from them apart from being a friend.