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Movies like Rule No. 1 (2003)

Caroline is forced to leave her unfaithful boyfriend, and the only place she can crash is with her sister Sarah, with whom she does not get along. Sarah graciously offers Caroline a tiny room in her apartment and decides to help her find Mr. Right. Caroline isn't sure she's cut out for the dating game, but Sarah assures her there's nothing to it. Caroline is sent on a series of grueling and comic dates with everything from nimble pickup artists, to adventure sports freaks and a karaokesinging stockbroker. But in the end what the two sisters really find is themselves.