Lisa tells Will is OK if he wants to go out with his friends one night and she will go out with her friends. They each lie about what they are going to do, and happen to both go to the same party. Worse, they find Ashley at the same party.
Will finds out what it is like to have a woman in his life that controls things. Also, Will lands a part in a soap opera and begins to see himself as a major star, spending money to fit his new status.
A family friend visits Philip. He asks WIll to do something illegal and Will tries to find a way to avoid the issue. Carlton and Hilary try to find a match in online dating and end up being matched with each other.
Will and Carlton compete for a job at Hilary's talk show. Will wins the job and has to take out a comedian's sister as part of his duties. Will is looking forward to it until he sees what the sister looks like.
Carlton is worried about the interview at Princeton and is afraid of another disappointment. Will does his best to check him up, but nothing seems to work. Carlton does not want to go to the interview, so Will goes for him.
Hilary tells Will that, as talent coordinator, he has to get better guests for her talk show. Will lines up a juror that has been dismissed from Philip's trial. When he goes on the show to explain why, Will and Hilary are in trouble.
It's Carlton's birthday. His father gives a trip to Vegas for Carlton and Will as a gift. Carlton becomes addicted to gambling and loses all the money as well as the return home tickets. They enter a talent contest to try to win the prize.
It's Thanksgiving time. Hilary's television show is filming at a homeless shelter; Hilary and Carlton go to the shelter to volunteer. Philip hurts his back; Will suggests they go to a massage parlor to help his pain.
Philip and Will get arrested at the massage parlor because the girls try to give more than a massage. Hilary and Carlton continue to volunteer at the homeless shelter and realize how fortunate they are.