On the same day Will finally has a date with Jackie, he has the opportunity to go to the Playboy mansion because Hilary, much to the dislike of Uncle Phil, has been asked to pose for Playboy.
Did You Know?
Hilary's mic is visible on the back of her red dress when she, Will, and Carlton first enter the Playboy party. It is gone in subsequent scenes. See more
[Philip and Vivian do not agree on how to raise Hilary
A girl should always listen to her father.
In that case I never would've married you!