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.

The episode was rated 7.69 from 205 votes.

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

The episode was rated 7.69 from 168 votes.

During an intimate moment, Nathan pops the question of marriage to Grace but she recoils simply because the situation didn't fit her childhood fantasy of a proposal. When she realizes her mistake, she returns the favor, but doesn't get the response she hoped she'd get.

The episode was rated 7.69 from 180 votes.

Will and Grace elect to disagree when it comes to choosing sides during a mayoral election; she supports the female Jewish candidate and he's voting for the gay nominee. To settle matters, the roomies host fund-raisers attended simultaneously by both aspirants.

The episode was rated 7.71 from 180 votes.

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.

The episode was rated 7.71 from 102 votes.

At the gym, Will spies another guy who looks maddeningly familiar, while Jack gets a workout as he keeps repeating one of his nonsensical catch-phrases in hopes of seeing it become popular among the sweat set. Meanwhile, Grace gets some bad advice from Karen when she seeks a loan to expand her company, so she stoops to asking her wealthy employee for the money—even if she has to resort to drastic measures to get the point across.

The episode was rated 7.72 from 174 votes.

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, when 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.

The episode was rated 7.73 from 141 votes.

After Will wins a portrait session at a charity auction, he takes Grace to pose for a notoriously eccentric celebrity photographer but the unfocused shooter's bizarre methods ultimately produce a funky image that flatters Grace and frightens Will. Meanwhile, Jack's back with another performance act, and this time he employs magic tricks but regrets using Karen as his assistant.

The episode was rated 7.74 from 159 votes.

Rosie O'Donnell plays Bonnie, a no-nonsense single mom who clashes with Jack over the raising of their son, Elliot, fathered from Jack's sperm-bank donation. Bonnie's enraged because Jack had 12-year-old Elliot's hair bleached blond, so she lays down the law. "From now on," she tells him, "stay out of my kid's life. I don't want you to see him again." A parallel storyline unfolds at a wedding gala, where Will poses as a tennis pro (because nobody likes lawyers); and Grace caustically toasts the bridegroom, her ex-fiancée. "I've always thought about having a child," she says. "But not as a husband."

The episode was rated 7.74 from 175 votes.

Will & Grace try to lure Tina, Will's dad's mistress, away from Will's father by setting her up with another man. Unfortunately the only man available is Will's gay friend, Larry. Also, Karen buys a horse for breeding, but the stud is more interested in stallions.

The episode was rated 7.78 from 168 votes.

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.

The episode was rated 7.80 from 155 votes.

After Will and Grace move into their expansive new dream apartment, they discover the awful pangs of separation anxiety as they pine for their smaller old digs now happily occupied by their friends who sub-let the place. Elsewhere, Jack tries to reconcile Karen with her estranged grifter of a mom, who wants to recruit her daughter for her next caper.

The episode was rated 7.81 from 151 votes.

Matt Damon makes a guest appearance as a clever charmer named Owen, who's competing against Jack for a spot in New York's Gay Men's Chorus. Truth be told, however, Owen is totally straight and is really after the group's big perk: a summer trip to Europe, all-expenses paid. Jack suspects Owen's ruse but needs proof. How about the hug test? Now a flustered Jack reluctantly turns to Grace to "in" Owen. Meanwhile, a scheming Karen tries to pass off an unwitting Will as her lover and not her lawyer when she discovers that she's the object of pity for being single at her own Valentine's Day party

The episode was rated 7.84 from 164 votes.

While a baleful Grace wallows in bed as she grieves over losing her boyfriend Nathan, an enterprising Will tries all his old tricks to spring her from her mattress and back into the real world's whirl. But when Jack and Karen arrive, Will fears that their bizarre efforts to help might actually drive Grace futher into her shell, not to mention therapy.

The episode was rated 7.92 from 182 votes.

This episode is also known as "Thanksgiving." Will and Grace join Jack and Karen in a motor tour of their respective families. (Double-length Episode)

The episode was rated 7.95 from 129 votes.