1987 film, directed by David Mamet. Intriguing story of how an intelligent, observant woman gets caught up in a confidence game.
Lindsay Crouse is Margaret Ford, a psychiatrist enjoying the fruits of a successful self-help book on obsession. One of her patients, a young man named Billy, threatens suicide over a debt owed to local gambler named Mike (Joe Mantegna).
Ford visits the man in an attempt to alleviate the problem, eventually threatening him with legal recourse if he attempts to harm her patient. During this initial visit, Mike askes her to pretend to be his girlfriend so he can beat a man in a poker game. The game was actually a ruse to extort money from Margaret. Fortunately, she catches on to the scam in time to stop it.
Despite their attempts to con her, she befriends Mike and his cronies. She returns to their hangout the next night, hoping to find Mike and learn more about the confidence games with which he's involved.
Mike remains somewhat aloof, speaking in cryptic terms, showing Margaret only a small offering of the scams he directs. She appears to become more and more attracted to him, and they eventually wind up in a hotel room (which he appears to con them into).
As they leave the hotel, he suddenly remembers that he's supposed to take part in a con on a visiting businessman. He tries to get rid of her as they approach the pre-arranged meeting place, be she convinces him to let her stay so she can see the con unfold. She eventually gets trapped in the scam and witnesses an unexpected violent conclusion to the event, for which she's indirectly responsible. Mike and his partner attempt to flee, using Margaret to aid their escape. In their haste, they manage to lose a large sum of money borrowed from mobsters and used as part of the scam. Desperate to help them, Margaret offers to give Mike the money before he's forced to skip town.
Margaret attempts to confront and justify her actions, and eventually returns to her office to hide, hoping that her part in the night's horrible outcome will fade. At this point, the story takes an unexpected turn, revealing to the frightened woman what really took place. The movie concludes with Dr. Ford's attempts to conclude the scam and extract a rather ironic resolution of her own.
The screenplay is typical of Mamet. The characters reveal only a small part of themselves to each other and the viewer. The dialog is intentionally stiff, almost rehearsed, with incomplete statements and character's lines stepping over one another. What you learn is how a cool, calculating woman manages to confront and deal with her own obsessions, some of which she never knew she had.