Despite her moving out (to across the hall), Will still feels that Grace clings to him, so she asserts her independence by having a dinner party without him. Meanwhile, to keep the INS at bay, Jack is forced to move in with Rosario.
When Grace feels that Will is abusing his power as president of the tenant's association, she runs against him. Karen tries to buy back Jack's forgiveness when she lets his beloved bird, Guapo, fly out the window.
A deceiving, but flattering, newspaper photo makes Grace look more "endowed" than she really is and gains her the attention of a former high school heartthrob who was never one to keep abreast of her before. Jack is destroyed to learn that Will had a fling with Walter, Jack's ex-boyfriend.
An unemployed Will agrees to serve as one of Jack's cater-waiters, until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video.
Will and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is.
Grace looks to Will for representation when a hotshot lawyer doesn't pay her for a consulting assignment, but he ends up making Will a job offer. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience.
Tired of Rob and Ellen's low-rent taste in dining, Will and Grace start hanging with a pair of hip downtowner's they meet at a sushi joint. But as the new pals paint the town, Rob and Ellen see red when they catch their best friends lying to avoid plans to dine at their favorite eatery: a coupon-crazy Italian chain in Secaucus. Meanwhile, Jack's inner child gets a little pick-me-up when he joins Karen at a PTA meeting at her stepchild's school.
When they appear on their favorite TV show, Antiques on the Road, Grace can't wait to dress down the guests who are ever hopeful that their tchotchkes are worth a fortune, while Jack just wants to undress the show's attractive appraiser, Porcelain Paul. But then it's all business when they realize that their junky, thrift-store teapot is actually valued at $30,000. Meanwhile, Will's new boss makes the reluctant lawyer kiss up to Karen in hopes of landing her hubby as a client.
Grace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm. Now Grace has to confront Will about Will being her "backup."
Will's ideal relationship with his loving father sours when his dad prepares to accept an award at his company's dinner banquet but tries to dissuade his son from attending because he's told everyone that Will is married to Grace. Meanwhile, Karen's private detective finds Jack's biological father.
Will and Jack appear on Today to protest NBC for cutting a gay kiss out of an eagerly-waited sitcom episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Elsewhere, Grace confides in Karen about dumping her boyfriend.
Will reluctantly agrees to go on a blind date set up by his boss and, to his surprise, has a good time, but he's hurt by the other guy's post-date silence, so he lets Jack coach him on how be a good date. Meanwhile, Grace's frustration with her too-laid-back boyfriend mounts, and she takes dubious relationship advice from Karen.
While on a blind date, Will finds out that Karen's husband Stan has had a heart attack and rushes to the hospital to be with the gang. Will, Jack, Grace, and Rosario all speculate on who Karen will turn to for her inevitable emotional breakdown. After all, who will pay the bills if Stan dies?
Will and Grace try to win Joni Mitchell concert tickets on a radio contest. Grace prays that they win and promises to help the less fortunate, And they won. But Jack reminds them of their vow. So they go to the community center and volunteer. They feel as if they've done their part and can go to the concert but they are told they need to be there on the night of the concert. And Grace wants to ditch it but Will feels obligated to be there. Jack helps Karen get rid of her old clothes and shoes and give them to the needy. But Karen leaves him alone and he unwittingly ...
When Rob and Ellen ask Will and Grace to be the best man and maid of honor at their wedding, Grace's sexy past with the groom is exposed when Ellen learns at her bachelorette party that Grace once slept with Rob. Meanwhile, Jack is confused by his reaction to the entertainment at Rob's bachelor party.
Despite their history, Grace spends a fun evening with Val only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home-an organization for gays who have converted to going straight, so he acts straight to woo the man.
It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a "Grace" of his own. Meanwhile, Karen must confront her most mortal enemy, the kitchen, when Stan requests a home-cooked meal for his birthday, and she looks to Jack and Ben to come to her rescue.
Grace is competing with a well known designer for a job. But she doesn't think she's good enough. So Karen shows Grace just how "perfect" the designer is. Jack has an idea for something he calls the subway tush which is a cushion that someone can bring when they have to be on the subway for a long time. So he wants Will to help him come up with the financing. Will refuses at first. But he later sets a meeting with some people, and Jack goes off and does something outrageous which Will thinks is embarrassing. Only the people they meet want Jack and not Will.
To help make peace between Grace and Ben, Will has them both over to dinner, only to have their relationship go beyond friendship. But then Will finds out that Ben is dating someone else. Meanwhile Jack catches Rosario in a clinch with a lover and learns that she wants a divorce.