A neurotic English teacher in New York City, Jake Singer (Whit Stillman regular Chris Eigeman) has more than his fair share of issues. He's barely on speaking terms with his father. His girlfriend recently walked out on him.
And then, of course, there's his mother's death - which he's still far from over. Anxious and depressed, he embarks on a course of psychoanalysis with Dr Morales (Ian Holm), a maniacal, vaguely sadistic Freudian who seems to be doing him rather more harm than good. Hope blossoms when he meets Allegra Marshall (Famke Janssen), a beautiful, widowed socialite with whom he soon falls in love - but what will the good doctor say?
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