Shopgirl (2005)

In Shopgirl, adapted for the screen by Steve Martin from his year-2000 novella, a 60-year-old man becomes deeply involved with a woman half his age. May-December romances tend to set off alarms, especially when written by 60-year-old men with the intent to star. So if you're going to write yourself this story, you had better excuse yourself by writing it well. Thankfully, Martin pulls it off. Claire Danes plays Mirabelle, a glove saleswoman for Saks Fifth Avenue in Beverly Hills. Bored and lonely, she's stuck in a sinkhole of depression, afraid to move for fear of sinking any deeper, but slowly, inevitably going under. Everything changes when she gets picked up by Jason Schwartzman's Jeremy, a blithely peculiar young man who takes her on one of the great film dates (great as in disasterous). Unsure whether to be flushed or crushed at her oddball catch, Mirabelle finds herself receptive to a new set of advances from Martin's wealthy, restless Ray Porter. To Martin's credit, Shopgirl makes a surprising amount of emotional sense, even within the rarified confines of its unavoidably flimsy romantic-fable plotting. Director Anand Tucker's elegant moodiness and three terrific performances make Shopgirl more than the sum of its mismatched parts.