Karen attempts to get Jennifer Lopez to listen to a song she wrote. Grace decides to get even with her cheating husband by stealing things from him.
Will feels part of a tug-of-war between his boyfriend and Grace. Jack competes with another dancer to win a spot with Janet Jackson and the dancer happens to be an ex of Karen.
Grace starts attending AA meetings because she likes the free food and therapy. Will and Jack attend a television focus group for OUT TV that lands Jack a new career.
Jack feels out of the loop when his coworkers make fun of him. Will and Grace decide they have a different approach to dealing with strangers.
Will decides to give his birthday a chance as he's finally in a good relationship. Grace learns that Vince is giving Will the key to his apartment. Karen learns of her lingering ties to Stan.
Grace has a hard time handling the case of a happy couple. Will enlists Jack's help for a troubled gay bookstore.
Will and Grace are surprised by the commonalities shared between them and Vince and Nadine. Jack brings Karen in as his assistant at Out TV.
After a great date with someone else, Grace comes home to a garbled message from Leo; Karen and Jack try to set each other up, but things go awry.
Grace's first date out post-Leo is ruined when she comes home to a message from him. Karen and Jack have a hard time with the dates they set each other up with.
Will, Grace, Jack and Karen go on a road trip for Grace s getaway weekend, but Jack and Karen hate the car ride and bail on the plan.
Will, Jack and Karen try to take Grace on a road trip to keep her mind off Leo, but Jack and Karen are quick to take off. Jack tries to decide on a face for Out TV.
Vince s mother cannot make her traditional holiday feast, so Will volunteers to make a special meal, but Vince s mother refuses to give him any credit; Jack gives Vince s sister (Jamie-Lynn DiScala) pointers on keeping secrets.
Will has a hard time getting thanks on Thanksgiving from Vince's mother when he steps in to prepare a meal in the wake of her injury. Jack offers Vince's sister advice while Grace and Karen make time with his brother who turns out to be sixteen.
Grace tries to shift the blame elsewhere when she breaks one of Will's mother's figurines.
A person from Karen's past tries to upset her status quo by taking over Walker Inc. Jack and Grace catch Vince with someone else while the two are enjoying a skip day.
Will frets about whether or not to bring Vince with him to a dinner party at the home of his boss, Margot, at which time she will select a new partner for the firm from a number of candidates. Grace also arrives at the dinner party, believing Margot has a blind date in store for her. Meanwhile, Karen thinks Rosario is faking a serious illness in order to get a raise.
Scott Woolley agrees to hire Grace as his restaurant designer if she'll fire Karen. Will is ticked when Jack abandons him on their boys night out.
Grace's protest of Valentine's Day ends when she falls for a greeting card writer. Scott Woolley tries to win Karen over with gifts, but she's distracted by an internet fling. Will and Jack end up in each other's arms for a dance after they're told that the club has a strict anti-gay policy.
Grace takes Will as back-up on her date with Nick. Jack falls for a hot gay nerd bird watcher.
When Karen gets Will to agree to fire her pastry chef, Will finds that task harder than he imagined because the pastry chef is hot. It gets tougher for all of them when the chef agrees to have sex with each of them. Jack doesn't help Nick break into television writing as Grace had hoped.
Jack and Will are lured to a new gay community where Jack buys a hoiuse for him and Will, but Jack's misread plops them in a house two hours away from their intended gay hot spot. The small, unsophisticated town kills them with kindness trying to get the two to stay as they feel that having gay people in their community will improve the town. Karen takes one of Grace's friends out drinking to cope with her marriage diff…more
Will is jealous of the friendship that Grace shares with his therapist after he recommends that she start seeing her. They then start to vie for a place in the doctor's upcoming book. Karen's new glasses greatly affect her view of the world and specifically Jack.
Will goes out on an literal blind date, but then learns that Jack has Pink'D him. Will eventually turns the trick around on Jack. Grace brings Karen to her father's birthday celebration and Karen falls for one of Grace's father's friends.
After Grace nearly dies in a clothing store incident, she decides to compose a will. This serious turn for Grace causes Will to make some choices of his own. Jack learns that someone took over his acting class after he abandoned it.
Grace receives a visitor in the form of her old college flame, but instead of being after her romantically, he seeks to hire her on to design the hotel that he and his wife just purchased. Jack is set to produce a talk show for the network with a tempermental former child star. Will decides that he wants to be a writer and meets a stranger in the park, Malcolm, who becomes interested in his work. Karen hosts a benefit.
Grace feels odd after her married ex tries to kiss her and decides that she can't decorate his hotel. Will's new "benefactor" works to get Will to go back to being a lawyer. Will eventually learns that Stanley is alive and behind the deception. Jack prepares to host his new talk show, but then it's suggested that Karen co-host.
Will's writing career fizzles, so Malcolm (Alec Baldwin) makes him another job offer, but Will gets suspicious when he finds himself in an empty office; Grace's college flame (Eric Stoltz) gives her a job decorating his new hotel.
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