Grace's visiting mom, Bobbi Adler, a would-be star whose propensity for breaking out into show tunes and impressions dismays her daughter – and delights Will, Jack and Karen – wreaks havoc by suggesting Will and Grace wed, despite their sexual differences. When Will winces at the fantasy of committing to anyone who needs to be the star of a relationship, Grace realizes she's more of a chip off the old block than she imagined.

When Rob and Ellen admit that they don't have fun playing games with Will and Grace because of Grace's competitive nature, Grace works to change her image. However, as Grace loses her competitive edge, Will's emerges and he convinces his partner to care only about winning. Meanwhile, after learning how to administer CPR from Jack, Karen saves a workman's life.

Grace is jealous when her mother stops match making for her, and instead sets Will up. Jack must convince an INS agent (who he dated once) that he and Rosario are happily married.

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.

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's delight in having a bright intern whom she can mentor turns into horror when the young woman re-makes herself into the spitting image of sassy, brassy Karen -- and that's at least one too many Karens to handle. Meanwhile, Will and Jack volunteer to act out scenes for a gay sensitivity seminar for the local police but the peaceful intent is lost when they tussle with two lesbian cast members who strongly object to their non-inclusive, sexist language.

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.

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.

After Stan is arrested for tax evasion, Grace and Karen timidly visit him in prison. Grace is so moved to help her worried friend that she moves right into Karen's deluxe apartment-in-the-sky, where she becomes a demanding guest who's soon hooked on servants, bubble baths and an extravagant lifestyle. Meanwhile, as Stan's attorney, Will struggles with stage-fright when he babbles on during a TV news interview, so Jack convinces him to polish his communication skills by attending an acting class ruled by an imperious teacher.

Will and Grace feel they need more elbow room, so they search for larger digs and find an exquisite place—despite the efforts of Sandra Bernhard—but to finance the move, they illegally sub-let their old apartment. Meanwhile, a well-intentioned Jack begins filming a documentary of Karen's colorful life to celebrate her birthday but accidentally stumbles upon her estranged, lowlife mom.

Will presents his newly reconciled parents with a cruise for their anniversary, but their individual secrets ruin his hopes.

After Will and Grace decide to have a baby together, obstacles pile up before them, including a missing specimen sample and bungled insemination efforts that have them teetering between artificial and natural means—all leading to mis-conceptions. Meanwhile, Jack considers giving up his show-business aspirations, until he gets some career advice from a ""divine"" entity: his idol Cher. Likewise, married Karen is sorely tempted by the romantic tickling of a rich and natty gentleman.

After stalking actor Kevin Bacon, Jack lands his dream job when the unsuspecting celebrity hires him as his personal assistant and immediately assigns him to find out who's been harassing him. Elsewhere, while Will and Grace wait for the right color to appear on their home pregnancy test, Grace is visited by a handsome doctor who makes her a tempting offer. In addition, Karen looks for a way out of her on-again, off-again relationship with the courtly and irresistible suitor Lionel.

Will finds a guy that he's interested in.

In the middle of her divorce proceedings, Karen learns that ex-husband Stan has suddenly passed away, and the funeral becomes a contest of wills between Karen and her British rival, and a free-for-all when the will is read for everyone who ever felt deserving, such as Will. Meanwhile, Grace is shocked when recently returned husband Leo is called back into service by Doctors Without Borders and asks her to make the trip with him to Guatemala.

When Leo invites his hip and trendy ex-girlfriend to a friendly dinner party, Grace turns to Will, Jack and Karen to round out the guest list and keep the night running smoothly. However, when Leo's ex turns out to be the only girl Will ever slept with, Grace's jealousy gets the better of her. Meanwhile, Karen discovers Lorraine's dog Chompers hiding in Stan's closet and searches for a new owner for the puppy.

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.

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.

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.