The Midlifers (2014)

Wade, a socially awkward nerd with a gambling problem, and Chuck, a narcissistic sociopath and self-diagnosed sex addict, are lifelong best friends, each in the midst of a midlife crisis. Their friendship is put to the test when Chuck gets dumped and invites himself to move into Wade's one bedroom apartment on the same night that Wade finally attempts to break the ice with his attractive, but emotionally unavailable neighbor, Cassandra.