High Quality Content by WIKIPEDIA articles! When Harry Met Sally... is a 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal as Harry and Meg Ryan as Sally. The story follows the title characters from the time they meet just before sharing a cross-country drive, through twelve years or so of chance encounters in New York City. The film raises the question "Can men and women ever just be friends?" and advances many ideas about love that became household concepts, such as those of the "high-maintenance" girlfriend and the "transitional person".