The Fresh Prince Of Bel-Air: Working it Out
Series 1, episode 25 from 1991.
Hilary gets a job as the personal assistant to a movie star (played by Queen Latifa).
She takes an instant liking to Will and tells Hilary that unless she sets up a date, she’s fired.
Will agrees, providing Hilary goes out with Jazz.
What could go wrong?
Movie pages here.