Everybody Wants to Be Italian(2008)

Jake, a lovelorn fishmonger who has spent nearly a decade trying to win back his ex-girlfriend gets involved in a romantic case of mistaken ethnicity. It's been eight years since Jake's girlfriend left him, and despite the fact that she's now married with three children, he refuses to move on. Fed up with their depressive pal's unwillingness to let go of the past, Jake's friends set him up on a blind date with a beautiful Italian woman from Boston's North End. Though Jake is convinced that such a woman would never consider dating a non-Italian, a quick crash course in how to fake it may prove just the trick to helping him learn to love once again.