Lieberman in Love

Lieberman in Love is a 1995 American short film directed by Christine Lahti. It won an Academy Award in 1996 for Best Short Subject.

At a resort, Joe Lieberman is attracted to a guest named Shaleen, who turns out to be a prostitute. They begin a professional relationship, which continues even after Joe develops a romantic interest in a woman who sells him a condo, Kate, who is married.

Source: Wikipedia