Will and Jack wake up in the same bed on the boat... and panic. Grace is already panicking because Leo forgot a bag on the boat and she found Dr. Morty's love letter addressed to him. But before Grace can head to Guatemala to stop Dr. Morty, she discovers that Leo's passport is in the bag too and Leo has to return to get it. But what should Grace do with the letter?
Grace and Leo are having a dinner party. Grace invites Will, Jack, and Karen, and when Leo bumps into his ex Diane, he invites her. Grace assures Will, Jack, and Karen that there will be no drama whatsoever. Absolutely not. Unless it turns out that Diane is a secret from someone's past.
Karen has invited Grace to the country club to play tennis. Will is going to Connecticut to see his mother and is taking Jack along for company. When Grace brings Leo along, Karen says she intended to play one-on-one with Grace. Karen has to accept a surprise partner for a doubles play. Tensions rise and Karen ends up revealing her true opinion about Leo.
Jack walks into Will and Grace's apartment, all full of himself and announces he has a part on a off-Broadway play opposite James Earl Jones. There's just one detail Jack forgets to mention to Will & Grace... Will's mother living under his roof is starting to get on his nerves. Grace wants to tone up because Leo's sex drive has increased.
When Leo's depressed about leaving Doctors Without Borders, Will tries to cheer him up. But it only makes him miss it more. And Jack decides to get ready for a Gay Spelling Bee and is being prepped by Karen.
Grace is abroad with Leo. Will has to take care of his injured mother and while in the park, they meet a man called Tom who also has to take care of his mother. Tom and Will hit it off, but the thing is, Tom really likes taking care of his mother, so Will has to fake that he too likes taking care of his mother in order not to drive him away. Karen is on the trail of Lorraine Finster and has tracked her to a hotel, but finds that the L. Finster who has checked in is actually her father Lyle.
Karen has to go have herself examined at a doctor and is scared to death. Will and Jack accompany her. Karen's fears are not diminished by the fact that the doctor is... slightly eccentric. Jack sees a good-looking male nurse and instantly decides to change from studying acting to studying nursing. And to do that he needs money from Will and Karen.
When Grace (Debra Messing) returns back to New York for her mother's birthday, Will (Eric McCormack) tries to coerce her into staying in town a bit longer so the two can spend some quality time together.
Will, Grace, Karen & Jack go to a restaurant to celebrate Jack's new start in studying nursing. Unfortunately, there seems to be a problem with their table reservation and things are only going to get worse.
It's Christmastime. Will is the first one in line for Barry Manilow concert, to the disappointment of the girl who arrives second. Turns out that they know each other through a Barry Manilow chat site. Grace happens to walk by and takes Will's place in the line while he goes to relieve himself. Then Grace spots her mother across the street, having dinner with Jack, even though she had said to Grace she wasn't coming to town. So, to find out what's going on, Grace calls Karen to take her place in line. Meanwhile, Will finds out that waiting in line for bathroom may ...
Lorraine's father, Lyle returns and tries to woo Karen but she rebuffs him. But changes her tune when Lorraine tells her to keep away from him. And Grace's sister who's a loafer comes to town to try out her new scheme. And when Grace tells her she's a loser and she turns things around and gets a job at a corporation which has Grace in awe.
Will succeeds where Jack fails: he becomes a boy-toy for a wealthy elder man. Grace drops a plate of hot noodles at a restaurant and declares war on them when they refuse to give her a replacement on the house.
Leo has a cabin in Vermont and his neighbor has called Grace to tell that the pipes have frozen and they need to be taken care of. Will is meeting a new, gay, client and can't go. Jack is going to see "The Boy from Oz", dying to see "Hugh Jackman ...and his huge ackman". So Grace has no choice but to take Karen with her. While they are on their way, Will meets the new client, who is a huge Lord of the Rings fan. After Jack has interrupted the meeting, the client declares, "I want him to be the lord of my ring"... In Vermont, Grace & Karen find something unexpected.
Jack is taking part in a cooking class because now that he has a boyfriend, he wants to offer him home-made food. Will goes too - and finds out that Jack brought Stuart with him. Not only is Will left cooking alone, he finds out that he is the only one who's single. Karen's mother has moved into town and is in need of a decorator - a lucky job opportunity for Grace.
Will and Grace who are now flippers (buying houses cheap and then fixing them up and selling them at a huge profit) are trying to get a house. But they learn that they have just encroached into the area of a couple of flippers known as Deirdre and Monet who are lesbians. They approach Will and Grace and tell them to stay out of their territory. Will decides to fight back by driving a wedge between them. However things don't go as planned. And Karen feeling as if she's cheating on Stan with her relationship with Lyle decides to contact him through psychic John Edward. ...
Karen enlists Will to teach her how to drive. And of course she gets pulled over by a police for speeding. Meanwhile, Grace and Jack are at movies. They see Stuart in the theater with another man and Jack starts suspecting Stuart is cheating on him.
Karen and Jack are facing a problem: not only has Sex and the City ended, but Frasier and Friends are ending too - what are they going to start following? Will dates a cop and makes the mistake of listening to Grace's dating advice.
Will and Vince's relationship is put to *the* test - will Grace approve of Vince? Meanwhile, while giving Karen dance lessons, Jack realizes that their relationship is most likely to change drastically when Karen gets married.
Elliott announces that he's going to apply into the school cheerleaders, which makes Jack very proud of him. Tina confides in Will that she suspects Will's dad is seeing another woman since he is now always too tired to have sex with her. Will has to go to see his father to find out what's the truth but he isn't prepared for the truth.
Jack is graduating from nursing school and because he was voted The Most Popular, he gets to make a speech - but then he realizes the graduation day is sooner than he thought and he needs to write his speech very very quickly. Enter Will to do it for him - a potential disaster.
At Lyle and Karen's wedding reception, Will confronts Leo, who is experiencing strong guilt about his actions. Lyle's brother also suddenly remembers he had something to tell to Lyle. And Karen has a surprise in store for everyone.