You're a Big Boy Now (1966) review

Sexually inexperienced Bernard (Peter Kastner), who works for his father I.H. Chanticleer (Rip Torn) at the New York Public Library and has a controlling mother (Geraldine Page), is forced by his parents to get his own apartment in the city with a busybody landlord named Miss Thing (Julie Harris), he goes on dates with co-worker Amy Partlett (Karen Black) but is totally enthralled with actress Barbara Darling (Elizabeth Hartman).  Although Coppola himself apparently doesn't care for this film and it does have him working in a genre (the "hip comedy") he doesn't really excel at, there are a few quirky elements to this, like Bernard's "friend" (and "poet") Raef del Grado (Tony Bill) offering him "romantic" advice, Miss Thing getting hysterical over everything and a nice depiction of a still-dirty NYC in the late 60's.  No offense to him, but Kastner (who lead a tragic existence) doesn't possess leading man qualities, and it's highly doubtful not one but two beauties would be clamoring to spend any amount of time with his insufferable character (even though he and Black were briefly in a relationship in real life), but hey ... anything is possible in the cinema.