Writer-producer Jennifer Westfeldt’s follow-up to her surprise hit Kissing Jessica Stein centers on Ira (Chris Messina), a neurotic New York Jew who enters into an on-and-off relationship with Abby (Westfeldt), a loopy, free-spirited shiksa. (Um, yeah—Annie Hall called, and it wants its plot back.) The overall effect is that of an aging vaudevillian making a good-hearted but embarrassing attempt to entertain us with stock characters and stock jokes and stock shtick. Westfeldt based the character of Abby on herself, which might explain why she’s a flawless, practically Christlike figure, persecuted by Ira’s anxieties and worshipped by doormen and cab drivers. If this seems unrealistic, it’s even
harder to imagine how a jobless grad student could afford Ira’s Upper West Side apartment. Ira and Abby is strongly invested in an idea of itself as a “New York movie,” but its self-professed love for the city is a sham.