On the eve of his graduation from nursing school, a nervous Jack turns to Will for help writing his commencement address. Reconnecting with his past dreams of being an accomplished playwright, Will over-analyzes the speech, searching for the life experience that sent Jack to nursing school as a source of inspiration.

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 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.

Grace and Karen are hired to decorate an apartment of a newlywed couple and they want their place to be all about love. Will Grace and Karen, two newly divorced women, be able to do the task? Meanwhile, a doomed bookstore gets help from Will... sort of.

The day before Will’s charity auction and carnival, Jack meets and begins dating Baby Glenn, who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties.

After winning concert tickets from a radio contest, Grace vows to get more involved and she volunteers herself and Will to help out at the community center. Unfortunately, her charitable work conficts with the concert. Meanwhile, while collecting clothes to give to the mission, Jack donates a pair of Karen's most-prized shoes.

Will expects two friends to arrive in New York to plan a wedding, but when the bride-to-be falls ill, he asks a willing Grace to work with the clueless groom to work out the details – but she gets a little too involved in the dreamy details and fancies herself a bride instead. Meanwhile, Will and Karen get chummy over a steamy potboiler book that they're both reading which leaves a jealous Jack fuming as the odd man out in the book-of-the-month club.

When Grace returns back to New York for her mother's birthday, Will tries to coerce her into staying in town a bit longer so the two can spend some quality time together. Meanwhile, Jack struggles with his new nursing teacher, Nurse Carver so Karen threatens her into letting Jack skip class and still make the grade. But, to everyone's surprise Jack discovers that he really misses nursing school and learning.

Dynamic enterprisers Will and Grace begin a new business venture as they buy old apartments to refurbish and re-sell for a tidy profit. When budding ""student nurse"" Jack bumps into his former acting mentor Zandra, the pair of entrepreneurs finds their first project apartment. Meanwhile, Karen renews her romance with Lyle Finster, but the couple's bliss is interrupted by an unfortunate houseguest when Lorraine moves in.

Enjoying the success of their new business venture, entrepreneurs Will and Grace help their apartment buyers Jack and Stuart settle into their new life under one roof. However, when Grace receives a higher offer on the apartment, the ""friendly flippers"" attempt to break up the happy couple by encouraging Jack's cold feet as they see a chance to make a quick buck. Meanwhile, Karen demands that Lyle finally discipline his unruly daughter Lorraine, nearly shattering the couple's budding romance.

Responding to the pleas of his father's mistress-turned-girlfriend Tina, Will attempts to discover whether there is a new woman in his dad's life. However, when his father's new mistress turns out to be his mother, Will must find a way to break the shocking truth to Tina. Meanwhile, Elliot's decision to try out for his high school cheerleading squad has Jack all smiles as he is determined to help his son make the team.

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."" Realizing he needs new material to get back into teaching, Jack changes his method to win back his students.

Karen is finally forced to come to terms with her feelings for her presumed-dead husband when Jack surprisingly tells her he thinks she belongs with Stanley, not Malcolm.

Will hires a cleaning lady to "rescue" his designing roommate Grace from the creative chaos that litters their apartment, and while preparing for an annual decorators' contest, Grace develops a dependency on her maid and can't create without her. Meanwhile, Jack poses as an attorney in Will's office to impress an attractive guy he hopes to date.

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.""

Grace is apoplectic when she catches Will's philandering father on the arm of a glamorous stranger, but she gets even more worked up when she tells Will -- and he's happy living with denial. Speaking of cheaters, Karen misunderstands Grace and suddenly suspects that her husband Stan is having an affair, so she sets out to even the score.

When Grace and Leo join Karen for a friendly game of tennis at her exclusive club, her fierce playing style sends Grace fleeing the court. However, when the reason for her angry play is her hatred for Leo, Grace is determined to find a way for them to get along. Elsewhere, a nervous Will suckers Jack into visiting his depressed mother in Connecticut hoping they can cheer her up.

When Grace's rebellious, free-loading older sister Janet comes to town to launch her new jewelry enterprise/folding table subway stand, Grace decides to put her foot down casting her sibling away. However, when her tough love prompts Janet to go corporate by taking a 9-5 job and studio apartment, Grace can't seem to handle her new image. Meanwhile, Karen continues to spurn Lyle's proposals of marriage, only to have a change of heart after Lorraine stops by for an impromptu visit, to declare her disapproval over Karen's ""relationship"" with her father.

Love is in the air as Will's slightly eccentric new client falls for Jack after he interrupts their meeting, but when Jack refuses to accept the romantic offer, Will sinks to bribing him in the hopes of furthering his career. Elsewhere, Grace and Karen take a trip to Leo's cabin in Vermont in order to fix the plumbing – and uncover a secret pile of cash in the master bed.

Opting to forgo a picturesque fall wedding to elope in Las Vegas, Karen hops a plane to ""Sin City"" with fiance Lyle and faithful friends Will and Jack but when she bumps into vacationing superstar Jennifer Lopez, she asks J-Lo to sing at the ceremony. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a freak design accident.

Jack and Jennifer Lopez return from her summer tour to relax, but a pushy Karen recruits Jack to help her get Lopez'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.

The group 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 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

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. While lunching at the mall they start making fun of people, but Karen's remarks are especially mean and Olivia and her friends take offense.

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 and she becomes overly critical of Jack.

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.

When Jack learns that Will never learned how to swim, Jack insists that he teach Will how. Meanwhile, Karen sets Grace up on a blind date with one of Malcolm’s friends.