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.
After breaking up with Leo, Grace tries to cope with her grief by taking all of Leo's stuff out of his apartment. After Leo shows up at Will's apartment to excuse and win Grace back, she seems to finally end their relationship. Karen writes a song, which she shows to Jack. She asks him to show it to Jennifer Lopez of whom Jack thinks she is his new best friend.
Jack prepares himself for his performance as a back-up dancer for Janet Jackson. During rehearsal Janet decides that she doesn't want 6 but only 5 dancers. This leads to a dance-off between Jack and another dancer, Artemis. It turns out that Artemis is Karen's former lover. Since she still has feelings for Artemis, Karen asks Jack to let Artemis win the dance-off. Grace still has to deal with the break-up with Leo and it takes all of Will's support to make her feel better. Will is so entangled by Grace that he almost forgets about his boyfriend Vince and that he got ...
When Grace accidentally walks into an Anonymous Alcoholics meeting she meets Val again. Grace is forced to participate in the meeting. As time goes by, Grace starts to like the meetings and thinks that they are just like therapy, but just cheaper. Karen fears she is losing Grace as friend to non-alcoholics beliefs. During a test screening for a gay network, Jack has many ideas. This annoys Will, who actually has got to say a lot about gay TV-shows, too and feels out-staged by Jack.
Jack feels misplaced in the TV staff of the gay network as he feels everyone is smarter and more educated than him. He feels as if he has to adapt to his co-workers, but this change would force him to change some things about his personality and to hate things he actually likes. When Will talks to someone living in the apartment house, Grace tells him not to do so since the person could be dangerous. When Grace meets the stranger in the elevator she invites him over to have some cocktails. As it turns out, the stranger is not dangerous, but a bit weird and boring.
It's Will's birthday and Vince wants to give him the key to his apartment as a gift. Grace thinks it is not a good and a rather cheap idea and convinces him to give Will a wallet instead. When Grace then tells Will at his party what Vince original present was, he is surprisingly excited and considers it to be very romantic. Will is of course very disappointed when Vince's present is not a key but a wallet. Grace is not brave enough to tell Will that she was the one who talked Vince out of the idea with the key. Karen is very upset since Will's birthday would also have...
Grace takes on her first job after the end of her marriage. What seems problematic about the job is that the clients are Newlyweds who just got back from their honeymoon. Grace is annoyed by all their flirting and their love for each other. When Grace leaves, Karen takes over Grace's job in the clients' apartment. Will takes Jack to a gay bookstore, which is about to be closed. Will finds out that the bookstore will become a gym after it is closed down.
Will and Grace meet Vince's close friend Nadine, who is "Vince's Grace". Vince and Nadine seem to be far nicer with each other than Grace and Will, which upsets Will. He wishes Grace was as supportive for him than Nadine is for Vince. When being forced to tell what she doesn't like about Vince, Nadine reveals that she hates Will. After quitting the job as Grace's assistant, Karen works as an assistant for Jack. But, rather than working, Karen and Jack only make nonsense, which forces Jack to fire Karen.
Grace decides to start dating again after her divorce. On her first date, she meets with a guy, who Will recommended to her. Although Will is worried that Grace ruins the date, it actually goes quite well and when Grace gets home there is a message on the answering machine from her date that he liked it and that he wants her to call back. The moment Grace wants to call back she hears another message on the machine, but this time it's from Leo. He reminds her of the fact that their anniversary is coming up. From that moment on, Grace is no longer interested in her date...
After taking Grace out of town to forget about Leo and their anniversary, Will and Grace stay at a hotel and Will hopes that Grace will finally find some peace. But, Will finds out that Grace has brought the answering machine with Leo's message on it with her and forces her to get rid of it so she stops thinking about going to the roof of Peninsula Hotel to meet Leo or not. Jack has to make up an idea for a promo for Out TV and meets the perfect actor for it in a hotel where he is working as a Bell Boy. Also, other people at the network think the actor is perfect, but...
It's Thanksgiving time and Will is about to meet Vince's family for the first time. Vince's mother apparently doesn't like any of Vince's boyfriends even if she hasn't met them yet. So, Will decides to take her out on a shopping trip. During the trip Vince's mother breaks her toe because Will told her to put on high heels and "work it". So, Will takes over the cooking job for Vince's family and his friends and everyone gathers for a nice dinner. Grace has crazy sex dreams which leads her to the conclusion that she needs sex in real life and sees a chance to get what ...
When Jack tell Will that Ro wants to come out of the closet and tell her family that she is a lesbian, he is about to freak out and tries to convince Ro not to come out tonight. Vince is still struggling with his suppressed anger for his dad, although he seems to do nothing that could upset his son. Grace and Karen both make out with Vince's cousin Sal and from then on compete for his affection. Annette keeps teasing Will, because of her injury, which he caused. Under all these circumstances, dinner seems to get a little messed up.
Karen's step-daughter Olivia visits her for Christmas, but Karen wants to get rid of her as quickly as possible so she makes Jack take care of her. Other than expected, Jack has a lot of fun with Olivia and Karen suddenly wants to hang out with them. Grace starts to get along with Will's mother pretty well until she ruins her favorite figuring. But since Marilyn doesn't know about it neither Will nor Grace tell her about it. The guilt over not telling Marilyn drives Grace nuts.