Mirabelle Buttersfield (CLAIRE DANES) is an attractive but shy woman who works the glove counter at Saks in Los Angeles. She hasn't had much luck meeting Mr. Right, unlike her more adventurous coworker Lisa Cramer (BRIDGETTE WILSON-SAMPRAS), and thinks that's still the case when Jeremy (JASON SCHWARTZMAN), a socially maladroit artist introduces himself to her at the laundromat and would like a date. Initially reluctant, she decides to go out with him and the two end up sleeping together.
But then she meets Ray Porter (STEVE MARTIN), an older, suave and decidedly sophisticated businessman who purchases some gloves from her and then delivers another pair to her along with a dinner invite. The two end up becoming an item, although he lays down the ground rules that he doesn't want to get into a serious relationship, a point that doesn't overjoy her, but she's so wrapped up in being swept off her feet that she doesn't care.
As Jeremy ends up traveling around the country on a rock and roll tour bus, Mirabelle finds herself falling even deeper for Ray. When he proves he wasn't kidding about the casual part, she must then decide what to do about her life, their relationship and Jeremy who's returned as a changed man.