黑帮大佬和我的第365Nate, a 19 year old film student, and Margaret, a 52 year old spinster, are best friends in an odd, quirky, totally working kind of way... until Nate's audacious classmate Darla sets him up on a date with James. Nate's new life shakes apart his friendship with Margaret, who goes off on her own to start a career as a stand-up comedian.