Young, innocent, and quirky June (Felicia Day), a violinist, spends her days working in an oddball Venice coffee shop, her nights rehearsing for a professional music career, and all-hours daydreaming about the beautiful man that's destined just for her. When she actually meets him in her own apartment building, she finds out Jack (Chris Henry Coffey) is engaged to the quintessential gorgeous bitch, Quinn (Cindy Dolenc). The conflict ensues and the romance is tested. Whether it's indulging her loony Grandma (Ellen Geer) through rehearsals of her own funeral, or dealing with the overzealous video-store manager (Ted Michaels) and his crush, June stumbles through her potential love life, her best friend Mary at her side.

Antonio is a seductive, charismatic Sicilian living illegally in New York. He wanders from job to job, lives as a squatter and enjoys a carefree romantic tryst with a wealthy art dealer. When he falls in love with Ellen, a strong-willed radio talk-show host who is set to move to Paris within a few days, he decides he must find a way to keep her from leaving.