First he approaches fellow comedian Maria Bamford, who only wants sex from him, and actually isn't satisfied by what she's getting on that front either. Trolling his daughter's school for available teachers doesn't turn up any prospects. But then he finds in bookstore clerk Liz (Parker Posey) the promise of that possible ideal combination of cute and good with kids when she offers him insight into the kind of books growing girls want to read and why. And he asks her out, and she says yes.
"My favorite part of New York is that you can just walk and walk and you never run out of city," Liz tells Louie in lieu of sharing with him what she actually herded them out of the bar. Throughout the evening she uses him as a kind of audience while she performs for his entertainment, always pushing to see how far he'll follow her down this path. And he's willing to go pretty far -- letting her goad him into trying on a dress at a vintage store (she laughs at him, but that plants a kiss on his lips and tells him that "you are official great"), buying into her story that she was given the name "Tape Recorder" by her indecisive parents. She confesses right off the bat that she almost died of cancer when she was a teenager, sometime that was obviously a formative experience for her -- unless she made it up. Did she make it up? It's almost unimportant, because even if it's the truth, as a thing to lay on someone you just met whose name you don't yet know, it achieves the same goal of off-kilter social aggression.
It's easy to see how Liz could be exhausting in any long-term sense -- and the exchange she has with the homeless man, in which he explains to her that he sees a snake on her face and she seems a little too prone to believe it, is one of several hints that she's not completely stable herself. But "Daddy's Girlfriend Part 2" has the kind of vivid, specific detail of a night out you'll always remember, whether or not you keep in contact with the person you were with. And Liz's final monologue, sitting on the edge of the roof, is a heartstopper, as the camera closes in on her sitting on the roof of that building against the skyline, telling Louie that he's afraid to come close because "a tiny part of you wants to jump because it would be so easy. But I don't want to jump, so I'm not afraid. I would never do that -- I'm having too good of a time."
A great turn from Posey, who's terrifying and enchanting in turn -- and well deserving of the Warhol screen test-style portrait she's given over the closing credits.