This engaging romantic drama set in New York City is based on a 1998 novel by Daniel Menaker and has been adapted for the screen by director Oren Rudavsky and Daniel Saul Housman. Jake Singer (Chris Eigeman) teaches English and works with the basketball team at a prestigious prep school. Although he comes across as very articulate in the classroom when talking about the artistic creations of Anton Chekhov or Albert Camus, he is an emotionally stunted person when it comes to intimate relationships. He is still grieving over the breakup with his girlfriend (Stephanie March); when he meets her on the street and she invites him to her upcoming engagement party, he is shattered. Jake never got over the death of his mother when he was a child, and he has a chilly relationship with his father (Harris Yulin), a surgeon. With all this baggage, he has been regularly seeing Dr. Ernesto Morales (Ian Holm), a Freudian therapist who is critical of his unassertiveness, sarcastic about his sex life, and relentless in his attempts to get Jake to take responsibility for his rudderless existence.
At a fund-raiser for the school, Jake doesn't know what to think when Allegra Marshall (Famke Janssen), a beautiful and wealthy widowed parent, flirts with him. He begins a torrid affair with her and at the same time re-establishes contact with his father. An incident at school with a troubled African-American boy on the basketball team calls out the fixer in him but he just doesn't have the energy to break through to the angry youth. A final slide into danger and confusion involves a bad decision he makes which has an adverse effect on Allegra's adoption of a little girl she loves dearly.
Writer and director Oren Rudavsky does a fine job conveying the relationship between Jake and his therapist, who may or may not be a figment of his imagination. The drama enables us to see how the course of our lives is deeply affected by the small choices we make and the ways we try to express love in difficult situations. Chris Eigeman and Famke Janssen keep us rooting for them as they struggle with the many obstacles blocking their path to happiness together.
