Julia Starr (JENNIFER MUDGE) is an Advertising Associate in present day New York City, who longs for the romance of a by-gone era as depicted in the movies and music of the 1920’s and 1930’s. Most nights, she stays up to watch the late, late movies on TV and the next day compares notes with her sassy older neighbor Ruth (RITA MORENO) who saw these films during their original theatre run. It’s fun but it doesn’t relieve Julia’s loneliness as she dreams of finding a man with whom she can share all her passions.

Julia’s work-life has become a struggle too. The new advertising campaign she is designing for a premiere client is not going well and her friend and co-worker Maryann’s (MICHELLE HURD) idea of romance is closer to a reality show than an Astaire/Rodgers musical comedy. At the end of their workday, Maryann is off clubbing with her many boyfriends while Julia wistfully rents ‘It Happened One Night’ at the video store. On the way home, Julia gets caught in a rainstorm and rushes under a doorway for cover. A moment later a tall and handsome man, Joe (CHRIS HENRY COFFEY), rushes into the same doorway – as their eyes meet Julia has that “movie moment” she’s been longing for.

Joe persuades Julia to stop by his apartment for an umbrella. When Julia enters she finds an antique Victrola with a box full of 1930’s music records and old movie collectibles on the walls – Julia thinks Joe is the man of her dreams. But the dream ends abruptly on Joe & Julia’s first date when she learns that all the music and movie memorabilia actually belong to Joe’s brother Robert (JOSH STAMBERG). Julia, despite her attraction to Joe, decides to follow her fantasies and pursue Robert, but which brother will be her destiny?

Through Julia’s struggles with work and love, and with a lot of advice from Ruth and Maryann, Julia learns to appreciate what’s right in front of her and stop daydreaming about things that might not be.