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- Gay lawyer Will and straight interior designer Grace share a New York City apartment. Their best friends are gleeful and proud gay Jack and charismatic, filthy-rich, amoral socialite Karen.
- When Grace admits she's not sure who's the father of her baby, Karen orchestrates a "Mamma Mia" situation with the potential baby daddies; Will worries what will happen if he has a straight son and enlists Jack to help him prepare.
- Will discovers a way to finally get back at Jack for years of mocking his hairline; Grace is determined to prove to Mrs. Timmer she's strong enough to handle being a single mother; Karen squares off against Stan's brother in a poker game.
- Will and Grace fight over whose process of having a baby is more difficult; Jack helps Karen prove that she'll be a competent owner of her new baseball team, but Karen realizes that an old acquaintance may be the help she really needs.
- In the aftermath of Will and McCoy breaking up, Grace and Jack hire the Grief Panda to help Will process his pain; with Karen completely occupied with her baseball team, Grace believes that she has to fire Karen in order to set her free.
- Committed to becoming a father on his own, Will meets a potential surrogate (Demi Lovato); to gain entry into AnnieCon, Grace pretends to be a formerly-famous Annie.
- Grace and her neighbor give their romance another shot, but an embarrassing incident puts Grace's relationship and dignity in jeopardy; Will cuts Jack off financially to get him to grow up.
- When Larry warns Will and Grace about the entry process into the elite school they want their kids to go to, they set out to prove that their child would be the better candidate; Jack creates problems between Karen and her booty buddy.
- Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man; Jack gets permission from his husband to sleep with his hall pass; Karen struggles to adapt when her assistant books them on an economy flight.
- Grace and her neighbor, James, give their relationship one more shot, but when James invites Grace to his job at the aquarium, she endangers his job and a species; Jack takes Will to an unexpected place to blow off steam -- church.
- Marilyn goes behind Grace's back to fix her up with a beagle-breeding couple interested in adopting Grace's baby; Will helps Karen deal with a PR nightmare; Jack and Estefan go to extreme lengths to get rid of a mouse.
- Karen introduces Will and Grace to the new love of her life. When Miss Coco Peru tells Jack that he's closing down his bar for good, Estefan encourages Jack to become its new owner.
- Will and Grace race to save Karen when they think she is in danger after her new boyfriend takes her to a cabin in the woods; Jack makes up a story to a reporter in order to keep his new bar relevant after its previous owner steps down.
- Jack helps Karen sneak into the manse to retrieve her ring, but they're shocked to find it on the hand of Stan's new girlfriend; while hosting Will's surrogate, Will and Grace become the old folks they swore they'd never become.
- Will ropes Dr. DiLorenzo into going on a fake date so he can spy on his surrogate; Grace struggles with popping her gender reveal balloon; Karen is torn between celebrating her team's championship and helping Jack with a Broadway audition.
- Will claims living with Grace is like Ricky living with Lucy; when Karen and Jack hear this, they each claim that they are the Lucy of the group; Grace, Karen and Jack each imagine themselves as Lucy, with Will as the Ricky to all of them.
- Karen celebrates her baseball team's championship; Will and Grace go to an open house, which leads to a conversation about their future living arrangement; Jack has to decide if he wants to stay in the city to pursue his dreams.
- Will is determined to not reminisce about his life in the city or his ex; Grace has false alarms of going into labor; Karen tries to get closure with her ex-husband; Jack's dream of taking a bow on a Broadway stage becomes a possibility.
- Eleven years after last being seen, Will and Grace's political beliefs are put to the test.
- Grace is shocked to find that the emergency contact called by her doctor's office is ex-husband Leo, not Will. Jack takes on a new job he never expected to love. Karen befriends a 12-year-old girl in the Bronx, despite her best efforts.
- Will starts dating a 23 year-old. Jack is worried about getting old and decides to try something new. Grace and Karen solve their differences about work in an automatic shower.
- 1998–202021mTV-PG8.1 (579)TV EpisodeGrace tries for her biggest job yet; Will is surprised to making Senior Partner; Beverley discloses his secret to Karen; Jack owns half of a winning lottery ticket.
- Karen has trouble dealing with a personal tragedy; Will, Grace, and Jack try to intervene; Will and Grace's new business relationship begins to show signs of stress.
- Will and Grace attempt to convince themselves it's okay to sleep with the same man; Jack and Karen get an annoying commercial jingle stuck in their heads.
- Will, Grace, Karen, and Jack wish they could have experienced Christmas in old New York City, but realize the past was not quite as romantic as they pictured it.