"Assisted Living" chronicles a day in the life of Todd, a janitor who spends his days smoking pot and interacting with the residents for his own entertainment. Todd's detachment from his surroundings is compromised only by his unlikely friendship with Mrs. Pearlman, a resident who begins to confuse him with her son. On this particular day, Todd must choose whether or not to play the part. "Assisted Living" is shot and staged in a real nursing home and gains much of its unique effect and style from the participation of actual residents and staff members. During much of the film, it is impossible to distinguish between what is real and what is fiction.

Carter (O'Bryan) wonders if he's ever going to find a woman who wants to be more than "just friends." His conniving best friend Pat and beautiful step-sister Erin (Vanessa Marcil) both know what's causing the problem: He's too nice! Having never taken them seriously in the past, Carter reconsiders when he meets Maggie (Sybil Temchen), a woman he feels just might be the one. Could it be time for this nice guy to finally start playing games? Set among the gorgeous backdrop of Kentucky horse country, "Nice Guys Sleep Alone" is a hilarious, touching and thoughtful romantic comedy.