Well...
Apparently, Lacy knows all of Wick’s past flings, and they don’t seem to be few, so the idea that Wick is a man with “little success with women” is something I really doubt. Wick knows how to flirt, and he even does it with Mitzi later on. Mitzi herself tells him that he wants all the benefits with her (romantic/physical?) without getting too involved in her business. That doesn’t make him “inexperienced” or unsuccessful with women. He already knows the game; he’s not a boy who can be easily manipulated.
I think it’s clear that Lacy is not happy about the interaction between Wick and Mitzi.
Even so, Wick seems sweet in his own way, and I think that’s what makes Lacy hold him in such high regard, to the point of supporting his interests in the rocks even without understanding why. Maybe Lacy is in love with him but hasn’t realized it yet, or maybe she feels a strong sibling-like affection and wants to protect him. Whatever the case, I think she’ll try to look after Wick when the time comes.
