Justin has two goals for sophomore year: to date Chuck, the hottest boy in school, and to become the king of Cool U, the table in the cafeteria where the "in" crowd sits. Unfortunately, he has the wrong look (short, plump, Brillo-pad curls), he has the wrong interests (Broadway, chorus violin), and he has the wrong friends (Spencer, into Eastern religions, and Mary Ann, who doesn't shave her armpits). And Chuck? Well, he's not gay; he's dating Becky, a girl in chorus with whom Justin is friendly.
In a world where plastic surgery is as popular as a pair of sexy Manolo Blahniks, suburban single mom Jessica Taylor is trying to make it past 40 with nothing more than moisturizer and a swipe of mascara. Her glamorous best friend, TV producer Lucy Baldor, has a different idea of aging gracefully. "My body is a temple," Lucy explains. "I just don't want it to crumble like St. John the Divine."
Julia, a hip, downtown salesgirl at Pelham's jewelry store, finds her social life turned on its head when she is asked to deliver a necklace to the store's young heiress, Lell Pelham, on Lell's wedding day. Beguiled by Julia's earnest cluelessness and her vintage-chic vibe, Lell and her gang adopt Julia, and "Eliza Doolittle" her into passing as the heiress to a family fortune, just for a laugh.