Samantha (Courteney Cox) is a travel journalist who is still recovering from the break-up with her last boyfriend, when her psychiatrist (Carol Kane) suffers a nervous breakdown. While Samantha is canceling her appointments, her new neighbor (David James Elliott) comes for a session. Having never met the real Dr. Rosenberg, she poses as her shrink in an attempt to steer him away from his girlfriend and towards her. Because of her new situation, Samantha ends up seeing a few of Dr. Rosenberg's other patients, including eccentric magazine salesman Henry (David Arquette). Thus leading her to question her life, including whether her 'perfect man' is actually what she truly desires after all.