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Commitment-phobic Manhattanite Lindsay (Estella Warren) realizes that she is teetering on the verge of a major epiphany when her psychiatrist leaves town for the entire month of August, and she's forced to take her therapy into her own hands. Immediately after rejecting a marriage proposal from her ideal mate, Lindsay finally begins to recognize the self-destructive cycles in her relationships, and prepares to work through them with her therapist. When Lindsay learns that her therapist has taken the entire month of August off work, and won't be able to speak with her until September, she attempts to find another analyst and discovers that the month long sabbatical has become the industry standard. Incensed at the thought of being left in the city without any guidance whatsoever, Lindsay and her pal Monica log on to "Craig's List" and organize a series of group therapy sessions with others who feel likewise abandoned by their therapists. It's during the course of those sessions that Lindsay meets AJ, whose best friend Max just happens to be pals with Monica's boyfriend Max. But while the chemistry between Lindsay and AJ is undeniable, the pair agrees to stave off sex for a month in order to get better acquainted. And their relationship is blossoming nicely until Lindsay's dream guy shows up looking for a second shot at love. Now Lindsay has a choice, and deciding which guy to spend the rest of her life with will be no simple task.