 Hilary lands a new job as an assistant to an actress, Marissa Redman. Ms. Redman turns out to be completely bossy. Will surprises Hilary with Jazz in the office and Marissa takes a liking to Will, wanting to bring him to a restaurant opening, she puts Hilary s job on the line if she can t set the date up. Will will only do it if Hilary goes on a date with Jazz.