Grace can't decide between Josh and Ben. Will returns home to find himself jealous over the bond Grace and Jack built while he was gone.
After Grace has a breakin attempt, she stays with Will, who is going mad at having both her and Jack living with him.
Will and Jack go to visit old friends that they soon discover aren't the party animals they used to be.
Grace gets a design intern who is quickly turned astray by Karen.
Grace is determined to end things with Ben. Jack finally finds success in his shows, but at Will's expense.
Grace gets offered to join in a three-way with an ex-boyfriend and his wife. When Will and Karen mock the mere thought of her doing such a thing, Grace tries to prove them wrong.
Will gets a free certificate to visit a psychic. Grace hires a waiter that she was responsible for getting fired, but it turns out he already has some work on the side.
Flashback to Thanksgiving 1985, when Grace is wanting to take her college boyfriend to meet her parents, but Will is realizing he may be gay and attempts to get help with that from Jack.
Flashback to Thanksgiving 1985, when Grace is wanting to take her college boyfriend to meet her parents, but Will is realizing he may be gay and attempts to get help with that from Jack.
Will and Jack are looking to date the same guy. Grace can't handle the man she's dating has six toes on one foot.
Karen deals with a coffee-addicted Jack. Will and Grace find themselves arguing when participating in a union ceremony of two friends.
Will and Grace wind up on Sandra Bernhard's bad side when she tries to sell her apartment.
Will attempts to impress a man who's a sportscaster, and Grace has to help him be more athletic.
Will struggles with his new relationship with Matt, who is still "in the closet" and refers to Will as his brother.
Grace feels guilty about selling her deceased uncle's car, and tries to get it back after Will sells it to a nun.
While Will's father is found to be cheating on his wife, Karen suspects Stan is cheating when she misunderstands something Grace says.
While Will's father is found to be cheating on his wife, Karen suspects Stan is cheating when she misunderstands something Grace says.
Will finds it difficult to break up with a guy he's bored with because he loves the man's dog so much.
Grace fights to stay in the poker games with Will and his friends when they tire of her behavior in the games.
Grace buys a piano thinking it will strengthen her bond with Will when she begins to think they are drifting apart. Upset at being dumped by his latest interest, Will starts writing trashy stories which capture Karen's attention.
Grace deals with a tacky new neighbor Nathan.
Grace goes to the funeral of a past school mate that she used to make fun of.
Grace desperately tries to keep her romance with Nathan a secret out of embarrassment.
Jack attempts to finally meet his father. Nathan moves in with Grace out of necessity and Grace has to deal with the resentment between him and Will.
Jack attempts to finally meet his father. Nathan moves in with Grace out of necessity and Grace has to deal with the resentment between him and Will.
