Will and Jack awake in a precarious position while at sea; Grace discovers love letters in Leo's bag from a female colleague.
Grace is vexed when she learns that Leo's ex-girlfriend (Mira Sorvino) is intimately acquainted with Will.
Karen invites Grace and Leo to play tennis at her exclusive club, but her fierce playing style drives Grace away.
Jack lands a speaking role opposite James Earl Jones in an off-Broadway play and gives the veteran actor some pointers.
Will takes Leo on shopping sprees and for high tea to help him rekindle his love of the city; Karen coaches Jack for the annual gay spelling bee.
Will takes his mother for an afternoon stroll and bumps into an attractive bachelor (Dylan McDermott); Karen continues her lifelong quest to hunt down hubby-stealing Lorraine.
An unorthodox doctor (Jack Black) gives Karen her annual physical; Jack begs Will to support his decision to become a student nurse.
Will urges Grace to stay in New York so they can spend some time together; Karen strong-arms Jack's nursing teacher into letting him skip class but still make the grade
Will catches the eye of a female diner after being stood up; Grace bumps into a man (Tom Everett Scott) with whom she once shared a forgettable encounter; Karen runs into her nemesis, Candice Bergen.
A weak bladder forces Will to entrust Grace with his place in line for Barry Manilow concert tickets; Grace's mother (guest star Debbie Reynolds) cancels their annual mother-daughter shopping trip to have dinner with Jack and Karen.
Grace's free-loading sister (guest star Geena Davis) comes to town to launch her latest business enterprise; Karen spurns Lyle's (guest star John Cleese) marriage proposals but has a change of heart when Lorraine.
A rich plastic surgeon (guest star Hal Linden) tries to buy Will's affection; Grace boycotts a new restaurant.
Will's new client (Dave Foley) falls for Jack; Grace and Karen discover hidden money while trying to fix the plumbing in Leo's cabin.
Will is the only single man in a cooking class full of couples, including Jack and his new boyfriend (Dave Foley); Karen's mother (Suzanne Pleshette) asks Grace to decorate her apartment.
Will and Grace begin a business venture selling apartments; Jack runs into his former acting mentor, Zandra; Karen and Lyle (John Cleese) try to renew romance.
Will and Grace try to break up Jack and Stuart (Dave Foley) so they can sell the apartment for a higher price; Karen demands that Lyle (John Cleese) discipline his daughter (Minnie Driver).
Real-estate entrepreneurs Will and Grace face formidable competition on the East Side from a lesbian couple (Edie Falco, Chloe Sevigny); John Edward gives Karen some psychic guidance.
Jack and Grace stumble upon Stuart (Dave Foley) watching a movie matinee in the company of another man; Will tries to teach Karen how to drive.
Grace advises Will to play hard to get with his new boyfriend (Bobby Cannavale); Jack and Karen despair after learning their favorite TV series will be going off the air.
Will introduces his new boyfriend (Bobby Cannavale) to overly critical Grace; Karen tells Jack that their friendship will change after her wedding.
At Tina's (Lesley Ann Warren) urging, Will tries to find out if there is a new woman in his father's life; Jack's son decides to try out for the high-school cheerleading squad.
On the eve of his graduation from nursing school, Jack turns to Will for help writing his commencement address.
Karen moves her wedding to Las Vegas, where Jennifer Lopez agrees to sing at the ceremony.
Karen moves her wedding to Las Vegas, where Jennifer Lopez agrees to sing at the ceremony
