Jack and Jennifer Lopez return from her summer tour to relax, but a pushy Karen recruits Jack to help her get J-Lo's attention for her newly written song, 'FYI: I Hurt, Too.' Meanwhile, Grace takes out her frustrations over her cheating husband Leo on a beat-up Will.
After Jack is fired as a backup dancer by Jennifer Lopez, she gets him an audition with Janet Jackson for her performance tour. Meanwhile, Will and Grace try to get back to business as usual and mend Grace's broken heart, only to have her come between Will & Vince.
Grace has a surprise reunion with Val as she attempts to steal doughnuts at an AA meeting. She gets hooked on AA meetings for free therapy and food and Val and Karen have a confrontation which leads to Grace's exposure as a fraud. Meanwhile, Will and Jack attend a gay television focus group, only to have Will kicked out and Jack hired as Junior VP of New Programming.
When Will and Grace meet a stranger named Ned in the elevator, Grace accuses Will of being too nice to people he doesn't know. While Grace befriends Ned and invites him to dinner, Will makes some nasty remarks about him, but they soon discover that Ned's not the best company to keep. Meanwhile, Jack is having trouble at his new company, Out TV, because he feels he can't relate to his co-workers after they mock him about his Cher doll. Karen and Rosario lend some much-needed support.
It's Will's birthday and everyone is in the mood for a happy birthday celebration, although Will is a bit hesitant because he has never had a happy birthday. Now that he is in a good relationship with his new boyfriend Vince, Will decides to give his birthday a chance. Grace runs into Vince shopping and notices that he has bought Will a key chain -- in the hopes of giving Will the key to his heart or apartment, and she tells him that Will would hate the gesture. Meanwhile, Karen is depressed because Will's birthday coincides with her late husband Stan's birthday.
Will convinces Jack to aid a local gay-bookstore owner to save his store from closing. Meanwhile, Grace's first design job after her divorce is for a young, obnoxiously-in-love newlywed couple. After a few conversations with the couple Grace decides she cannot do the job because she cannot bear being around them. Karen decides to help Grace out and completes the job for her with an uncharacteristic flourish. Grace can't bring herself to give Karen any credit for the job that Grace couldn't bear doing herself, resulting in Karen quitting her job as Grace's assistant.
When Will and Grace invite Vince and his straight female friend, Nadine, over for a meet-and-greet dinner, they find to their horror that their guests are actually polar opposites of themselves. Meanwhile, Karen is still angry with Grace and decided to leave the firm when Jack comes to her rescue and hires her to be his new assistant at 'Out TV'.
Grace comes home from a great date and listens to a staticy message she's received from Leo. She thinks Leo is telling her happy anniversary and that he wants to meet on the top of the Peninsula Hotel as they had always planned. Grace hides the message from Will, but when Will learns about it, he decides to take Grace to the Berkshires to get her mind off of Leo. Meanwhile, Karen and Jack try to set each other up. However, after Karen gets paired with her gardener and Jack is set up with a straight, married guy, Jack and Karen decide they are the best people for each other.
Will, Grace, Jack and Karen go on a road trip for Grace's get away weekend -- a weekend devoted to not mentioning the name 'Leo.' Jack and Karen hate the car ride and quickly decide to bail on the plan. Elsewhere, when Jack spots Peter, a 'sinfully delicious' man who Jack remembers from a cocoa commercial when he was a kid, he recruits him to be the new face of 'Out TV,' much to the surprise of Rip Taylor who also wants the gig.
When Vince's mother injures her leg and is unable to make her traditional Italian Thanksgiving, Will comes to the rescue by offering to make his own special dinner -- but Vince's slap-happy mother refuses to give Will any credit. Meanwhile, Jack gives Vince's sister Ro a few pointers on a big secret she is keeping from her family and fianc?. Elsewhere, Grace and Karen get very cozy with Vince's much younger cousin.
When Vince's mother injures her leg and is unable to make her traditional Italian Thanksgiving, Will comes to the rescue by offering to make his own special dinner, but Vince's mother refuses to give Will any credit. Meanwhile, Jack gives Vince's sister Ro a few pointers on a big secret she is keeping from her family and fiancé. Meanwhile, Grace and Karen get very cozy with Vince's much younger cousin.
Grace attends a holiday party at Will's mother Marilyn's home and accidentally breaks a treasured Lladro figurine. Will convinces Grace not to tell his mother and to blame the accident on one of the other guests at the party. Elsewhere, Karen's stepdaughter, Olivia, comes to stay for the Christmas holiday and Karen pawns her off on Jack, who fits right in with the teenage girl and her friends.
Scott Woolley, an old high school classmate seeks revenge on Karen for ruining his senior year by trying to become president of Walker, Inc. After Scott prepares a presentation that wows the board of Walker, Inc., he takes over control of the company, much to Karen's dismay. Meanwhile, Jack and Grace take the day off of work to go to the movies. While at the supermarket getting snacks, they run into Vince and his co-worker and assume that Vince is cheating on Will.
Will is up for partner at his law firm. His boss, Margot, invites the candidates for partner to a dinner at her house, where she will ultimately make the final decision. Will, who is worried that Vince will ruin his chances of getting the promotion, is reluctant to bring him as his date. Grace also attends Margot's dinner party under the pretense that Margot has set her up on a blind date. Once there, Grace realizes the blind date is with Margot's husband. Elsewhere, Rosario becomes sick and Karen refuses to believe she is really ill.
Scott Woolley, under the alias Mr. Osment, hires Grace to design his new restaurant under the condition Grace fires Karen from her design firm. Grace later tells Karen about the incident and they realize the man that hired Grace is really Scott Woolley. Meanwhile, Jack takes Will out for a boys' night to get his mind off of Vince, but ends up ditching Will.
Valentine's Day is full of surprises. Grace tries to ignore the greeting card holiday but romantic urges eventually send her into the arms of the enemy -- none other than Nick, a hunky greeting card writer. In a dramatic change of events, Karen's former nemesis Scott Woolley tries to win her heart by showering her with gifts but Karen's eyes are on larger things -- her new overweight Internet date. Elsewhere, after dancing with a lesbian couple Will and Jack find comfort in each other's arms for the Valentine's Day spotlight dance.
Grace drags Will along to keep her in check during her first date with Nick only to leave a heated Will at his table for one. Meanwhile, Karen hatches a wild plan to get Jack a date with Aaron, the neighborhood bird enthusiast, only to ruffle some feathers when things don't quite go as planned.
Will agrees to fire Karen's pastry chef until the baker cooks up a delectable love triangle for the three of them. Meanwhile, Grace enlists Jack's help in launching boyfriend Nick's career as a television writer, but Jack shatters Nick's script-writing dreams.
Jack convinces Will that they need a change of scenery and should buy a vacation home in Middleborough, an up-and-coming gay community. After purchasing a new pad, the duo find out that it is not quite the gay getaway they had imagined. Instead, Jack landed the two in a blue collar town just two hours away from the newest gay hotspot. Meanwhile, Ellen asks Grace to babysit her three children, but changes her mind when she finds out Will is out of town.
When Will convinces Grace to see his therapist, Dr. Georgia Keller, he becomes increasingly jealous when the two women form an instant friendship. Grace and Will begin to compete fiercely for Georgia's attention -- and a place in her upcoming book. Meanwhile, glasses bring Karen to a whole new level of clarity.
When Grace convinces Karen to accompany her to her father Martin's birthday bash, the situation turns awkward when it is just the three of them. Struggling to gain the attention of her seemingly aloof father, Grace tags along with him to the golf range in hopes of scoring some quality bonding time. Meanwhile, Karen keeps herself entertained with Martin's buddy, Burt Wolfe. Excited about the date that Jack has arranged for him, Will discovers the true meaning of the phrase 'blind date.'
After a near-death experience in a jean boutique, Grace decides to write her will and enlists Will's legal expertise. To make sure she's fair when bequeathing her money, Grace visits Will's mother to find out how much Will plans to leave her and is shocked by what she finds. Thanks to Grace, Will also takes a look at his life and decides it's time to make a life altering career move. Meanwhile, Jack and Karen find an imposter teaching Jack's McFarland Method of acting.
Having quit his job at the law firm, Will turns to a career in writing where he catches the eye of Malcolm, who claims to have high-profile connections -- but when his writing career fails, Malcolm has another job offer for Will. Meanwhile, Tom, an old flame from college, returns to ask Grace to design a hotel that he and his wife just bought -- only to discover that there are still romantic feelings between the two of them. Jack struggles to produce his latest show for Out TV, but spoiled child star Randall fails to embody Jack's vision. Under threat of a lawsuit, Karen is forced to publicly apologize to Beverley Leslie for an embarrassing rumor.
After his first day, Will becomes suspicious of his new job - especially when he finds himself in an empty office with no co-workers, a German shepherd and a Russian-speaking thug.