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Rafi is a recently divorced, 37-year-old career woman from Manhattan who becomes romantically involved with David, a talented 23-year-old painter from the Upper West Side. Rafi shares all her secrets with her therapist Lisa who, unbeknownst to Rafi, is David's mother. Lisa is supportive of Rafi's relationship with a younger man before she learns who he is, discovers the connection and finds herself not only faced with the ethical and moral dilemma of counselling David's girlfriend, but also the reality that she feels differently about the relationship now that she knows her son is involved. Lisa consults her own therapist, and they decide that it is in the best interest of her patient Rafi for Lisa to continue treatment, as long as the relationship remains the "fling" it appears to be.

However, Lisa soon realizes that the relationship is serious, and tells Rafi that she is David's mother. Feeling embarrassed and betrayed, Rafi ends her treatment with Lisa. Their differences causing problems between them, Rafi and David break up. A couple of weeks later, David is enjoying a night on the town with his best friend; he gets drunk and ends up sleeping with Sue, Rafi's friend from work. The same day, after bumping into each other at the supermarket and going back to David's place, David and Rafi start seeing each other again. They also try to make the relationship stronger by going to a Friday night dinner with David's family. The rift between Rafi and Lisa is patched up, although Rafi brings up the possibility of her and David having children, to which Lisa reacts strongly. A few days later, Rafi discovers that David had slept with Sue, and David and Rafi fight. After sulking for some time, David goes to seek Lisa's help as both his mother and as a therapist. She advises him to do what he can to keep the relationship, because it was through Rafi that Lisa was able to understand David's career as an artist. David goes back to Rafi to apologize and offer to give her a child because that is what she wants the most. Rafi realizes how deep David's love must be for him to make such a sacrifice. Somehow, they both conclude that love is not enough to keep a relationship going, and they break up.

A year later, David and his friend are seen leaving the first restaurant where he and Rafi had their first proper date. Going back to retrieve his forgotten hat, David spots Rafi but she does not see him; he gets his hat, rushes out the door, and hides. He defrosts the glass a bit to watch her, and she turns around and sees him. They share a smile before parting.

• Meryl Streep as Lisa Metzger Bloomberg
• Uma Thurman as Raffaela "Rafi" Gardet
• Bryan Greenberg as David Bloomberg
• Jon Abrahams as Morris
• Zak Orth as Randall
• Annie Parisse as Katherine
• Aubrey Dollar as Michelle
• Jerry Adler as Sam
• Doris Belack as Blanch
• Ato Essandoh as Damien
• Naomi Aborn as Dinah Bloomberg
• John Rothman as Jack Bloomberg
• Madhur Jaffrey as Rita
• Lotte Mandel as Bubi

The role of Rafi was originally going to be played by Sandra Bullock. Bullock completed rehearsals with Younger and Greenberg, but pulled out just before filming began, because she wanted major script changes, and the director was not willing to change the script.

Bryan Greenberg's trip to New York to film this movie is documented as part of HBO's semi-reality series Unscripted.

The soundtrack is a mix of different music genres such as jazz and pop. The composer of this soundtrack is Ryan Shore.

Critical response

Rotten Tomatoes gave the film score of 50% based on 117 reviews. Metacritic gave the film a weighted mean score of 58% based on 32 reviews

Box office

The film opened at #3 at the U.S. box office, making $6,220,935 USD in its opening weekend, behind The Legend of Zorro and Saw II.