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.