After a newly independent Grace moves into an apartment across the hall, she decides to throw a dinner party all by herself. Will isn't invited, but he has a date. Meanwhile, to solve problems with the INS, Jack moves in with his new bride Rosario in the maid's quarters at Karen's.
Grace gives Will a run for his money when she enters his unopposed race to be named tenant-board president after she finds out about the position's perks. Meanwhile, Jack hits the jackpot when Karen tries to buy his forgiveness after she loses his pet parrot Guapo.
A deceiving, but flattering, newspaper photo gains Grace the attention of an old crush who was never one to keep abreast of her before. Meanwhile, Jack is destroyed to learn that Will had a thing with his former fling.
Grace hits the roof when her matchmaking mom visits with yet another man in tow: one of Grace's childhood friends. At first Grace is infuriated by her mom's matchmaking, but her anger soon turns to disappointment when he turns out to be a perfect match...for Will. Meanwhile, Jack and Rosario meet with an INS agent who's well acquainted with Jack's past.
With 90 percent of his practice now devoted to the wealthy Harlin Polk, Will dismisses all of his smaller clients, who believed in him before he became a success. But when Harlin's deal falls through, Will finds himself out of work. Meanwhile, Karen's husband Stan puts his foot down and tells her to quit her wild spending, and Grace steps in to help her friend master the art of living within a budget by taking her outlet shopping.
After Will closes his office, Jack challenges him to become a cater-waiter on his staff; Meanwhile, Grace finds out a dirty secret about Karen when she catches Karen at work....in an adult film.
When Will and Grace meet Jack's mother and learn that not only is she unaware that her son is gay, but she also believes that he has had a romantic relationship with Grace, they invite her to Thanksgiving dinner with Jack hoping to force the issue into the open. But nobody is prepared for the holiday surprise that she has for them.
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.
Friends Rob and Ellen are feeling neglected when Will and Grace begin hanging around with a hipper, younger couple: rock 'n' roll photographer Kai and art-gallery manager Naomi. Meanwhile, Jack and Karen help each other through a parent-teacher conference for her step-kids.
When Ben tells Will that he has until Friday to find a new client or lose his job, Will kisses up to Karen to appease his new boss. Jack and Grace try to get on their favorite TV show and then get into hot water over an antique teapot.
When Will's best friend from high school asks Will to be the father of her baby, a jealous Grace tries to thwart her baby-making plans.
Will's sexy dreams about Grace land him in therapy and send her on a couch trip with his hunky shrink. Meanwhile, Jack and Karen clash over her treatment of Rosario.
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 yanking a gay kiss from a sitcom episode. Meanwhile, Grace seeks Karen's advice on dumping a weirdo beau.
When Will is set up on a blind date by his boss, he has internal debates on whether or not to go. Of course, Jack gives Will advice on how to be a good blind date. Meanwhile, Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice.
Will's former boyfriend, Michael, is back in town and may want to rekindle their relationship. Meanwhile, Karen tries taking her 'career' more seriously and asks Grace for greater responsibilities.
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?
After winning a call-in radio contest for prized concert tickets, Grace vows to reciprocate and volunteers her time to charity, but when she recruits Will to join her at a community center, she quickly begs off her commitment when it conflicts with her busy social calender. Meanwhile, Karen and Jack don't escape either from Grace's newfound charity which forces Karen to rifle through her closet -- and allows Jack to accidentally donate a pair of Karen's most-prized shoes.
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.
Grace suspects Val may have stolen her music box and tries to convince Will that their neighbor is a kleptomaniac. Meanwhile, a gay man trying to go straight tries to convert Jack into a non-practicing homosexual.
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 homecooked meal for his birthday, and she looks to Jack and Ben to come to her rescue.
Grace is thrilled when, thanks to Karen's social connections, she gets the chance to land a prestigious client for her interior-decorating firm. The only problem? She must compete with international design goddess Helena Barnes. To help boost Grace's confidence, Karen assumes the alias of 'Anastasia Beaverhausen' to dig up dirt on the socialite. Meanwhile, Jack tries marketing an odd invention: a tush pad for riding the New York City subway.
Will promises not to interfere when he learns that Grace has gotten romantically involved with his boss, Ben. Meanwhile, Jack finds Rosario having an affair with Gardener, and she requests a divorce from Jack, who fears losing Karen's financial support.
Forced by his boss to betray both of his friends, Will quits - only to discover that everything isn't as it seems. Frustrated, he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up.