Synopsis: Always Say Goodbye is a romantic dramedy in which struggling photographer and bachelor Nick Evans (Joshua Beckett) eventually meets his match in Anne Kidwell (Marcia Cross), a sexy, good-humored clothing designer who challenges his sense of personal and creative responsibility. While Nick imagines that he has to be a surrogate husband to his sister, who is having a baby on her own, and a caretaker to his recently divorced mother, Anne convinces him that he is his own worst enemy.