Will & Grace - Season 5 (2002)

Karen and Jack hatch a plot which gets Will and Grace into the same place at the same time, in the hope that they will get back together.

Karen struggles with the decision whether to tell Stan about her affair, only to find out that he is also hiding something.

Will's budding interest in a fellow lawyer in his office is nipped upon the arrival of his firm's aggressive new boss, who whips the troops into shape and orders Will to fire his friend.

When Grace accompanies Leo to dinner with some "friends," she doesn't realize that he's tricked her and instead introduced her to his real parents--and she soon regrets her earlier salty dialogue and suggestive attitude. Elsewhere, Jack is again confronted by Zandra, his gruff acting teacher, when he tries to showcase his meager talent in a class while a willing Will joins Karen in subjecting to a Botox facial injection.

After Grace impulsively accepts a marriage proposal from Leo there seem to be a million roadblocks between her and an actual wedding, not the least of which is her best friend Will's unease about the whole idea.

Grace and Leo deal with unsettling details; and Will is reluctant to give away Grace.

After a displaced Karen is booted from her Palace Hotel digs, a sympathetic Will agrees to let her move in with him-at least until she turns his apartment into a federal disaster zone with her exorbitant lifestyle, forcing Will to try and unload her onto Grace's shoulders. Meanwhile, Jack loses style points when he poses incognito out of fear that the "Gay Mafia" has it out for him.

"On Christmas Eve, Grace is torn when she has only two tickets to "The Nutcracker" musical and can't take both her best friend Will and new husband Leo (Grammy-winning guest star Harry Connick, Jr.)- but her back-and-forth indecision leaves Will spinning like a Hanukkah dreidel between a dithering Grace and his previous holiday plans with Jack and Karen."

"When Jack convinces tangle-footed Will to join him on a gay soccer team, Will's inept playing leaves him warming the bench - which allows him to bond with the teenaged Elliot, who also is the last man called upon with his own youth soccer team. Meanwhile, Grace is delighted that Karen is giddy in anticipation of her date with a handsome restaurant owner (guest star Andy Garcia)."

Grace meets her new neighbor, Julie, who surprises her in more ways than one... Will goes to a blind date with Karen's cousin Barry, who, although gay, also has some surprises of his own.

Will and Jack continue their campaign to adapt Karen's awkward cousin to his new way of life but their flamboyant efforts to help him only remind Will of his own clumsy experiences when he came out.

Lorraine tries to lure Jack away from Karen; and Will and Grace struggle connecting after spending so much time apart.

Grace is having a girls' night. Jack hires his old babysitter - "a crazy lady with a rockin' body", as Will puts it - as his... babysitter.

Barry returns from fat camp and goes through a makeover. Then Grace claims that she sees all the signs in Will - he likes Barry! Will denies it, but could Grace be right?

A jealous Will keeps a wary eye on the re-modeled Barry when he spies him disappearing with Jack while Karen switches roles with Rosario and pretends to be a maid in order to court a handsome maintenance worker.

Still nursing a grudge over his last failed relationship, Will forms a gin-soaked anti-romance club with other lovelorn losers, Mr. Stein, and Karen - but the threesome shrinks dramatically when Stein takes a shine to the ever-ready Karen.

Will's attempt to orchestrate a surprise for Grace's birthday by sneaking Leo back from Africa fails when he arrives earlier than expected. After Grace bumps into Leo, they agree to an elaborate charade to keep Will's 'surprise' intact.

Will sprains his foot and Grace and Jack try to help Will through his pain and Karen gets a new roommate.

Stan dies while having sex with his mistress. The divorce is not yet final - will Karen inherit it all or is there a change in Stan's last will?

Karen learns that 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.

Karen confronts her ex-husband's mistress before she invites Will, Grace and Jack on her extravagant yacht for a somber ceremony.