When Karen's 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.

Jack is stunned to learn that his estranged son, Elliot has a son of his own, Skip. Moreover, Skip needs the kind of help only Will and Jack can provide. Grace and Karen behave badly with the hot new guy at work.

Will, Grace, Jack and Karen attend the wedding of Will's ex-boyfriend, Vince. While Grace tries to keep Will from making a scene, Jack learns that his wedding hookup has many strings attached.

A baby shower makes Grace and Will question their life choices. Karen and Jack find a way to combine child labor with musical theater. Jennifer Lopez will pull double duty guest-starring as both herself and her "Shades of Blue" character, Det. Harlee Santos.

Will rekindles a relationship with his first love against Jack's advice. Grace reluctantly fights for Karen's civil rights when a bakery refuses to make a cake she wants.

In order to land a handsome, gay TV news anchor with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid. Karen learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster, so she enlists Grace to go with her to the strip club where Lorraine works. Olympian Adam Rippon has a cameo as a barista with an attitude.

Will, Karen and Jack unknowingly take a hallucinogenic drug, which causes Will and Jack to wonder if they're each other's soul mate and has Karen giving her last "performance" as Mrs. Stanley Walker. Meanwhile, Grace is shocked when her high-powered client takes up with her sister Janet.

After her dad, Martin, is rushed to the hospital, Grace is shocked when he refuses a transfusion of Will's blood. Will's mom, Marilyn, uncharacteristically takes Martin to task. Karen's demands cause Jack to uninvite her to his wedding.

Jack and Estefan's wedding takes a detour when they're forced to get married at the airport by their friend Miss Coco. Will's worried his relationship may turn long-distance. Grace meets a charming guy. Karen reconsiders her commitment to Nikki.

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, Grace and Jack are upset when they discover they’ve been too preoccupied with the changes in their own lives: Will teaching law at Columbia, Grace running for president of the New York Interior Designers Society and Jack’s new relationship with Estefan to even notice Karen has not been seen in days – ever since her husband found out about her affair with Malcolm.

Will and Jack visit Jack’s grandson, Skip, in Texas to watch him perform at his church’s talent show. But when Jack learns Skip plans on singing “Diamonds Are a Girl’s Best Friend,” he becomes afraid for his grandson’s safety. Karen tags along to check out the portion of the border wall she sponsored, only to discover that Beverley Leslie has claimed it as his own. Grace and Noah try to figure out if something is wrong in their relationship because their attempts to have sex have failed.

Now a certified psychic, Jack channels Rosario to help Karen open her heart to love again; Grace learns love means having to say you're sorry... to Will.

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.

Committed to becoming a father on his own, Will meets a potential surrogate with stellar reviews, but her lifestyle choices give him doubts. In order to gain entry to AnnieCon, Grace pretends to be a formerly famous Annie.

Jack's first day as a Lyft driver goes south when he rear-ends a wacky neighbor. An old friend decides he's in love with Will. Tim Bagley and Molly Shannon guest star.

Jack's intimacy issues are challenged by a closeted boyfriend. Will and Grace sell their new line of bedding on TV.

Grace reveals a secret from her past to her father, changing their relationship forever; legendary drag queen Miss Coco Peru emcees a lip-sync monologue throwdown to determine who will be Jack's best man, Will or Karen.

Will gives local newscaster McCoy Whitman a second chance and, with the help of Jack, finally gets to know the man behind the newsman. Grace's campaign for Design Guild President hits a snag when the deciding vote comes down to her old nemesis, Val. Karen acts as Grace's campaign manager, and attempts to secure Val's vote by any means necessary.

Grace returns from her European travels a new woman, but her elation is short-lived when she receives life-changing news. Karen teaches Will how to be better at phone sex. Jack has a yard sale to discreetly get rid of Estefan's annoying cuckoo clock.

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 new baseball team, Grace believes that she has to fire Karen in order to set her free.

When Larry warns Will and Grace about the difficult entry process into the elite school they both want their kids to go to, they set out to prove that their child would be the better candidate. While helping Jenny with her ASMR livestream, Jack unwittingly creates problems between Karen and her “booty buddy,” Luke.

Worried about Grace being a single mother, Marilyn goes behind Grace’s back to fix her up with a beagle-breeding couple interested in adopting Grace’s baby. Will gets enlisted by Karen to deal with a P.R. nightmare created by a homophobic player on her baseball team. Jack and his husband, Estefan, go to extreme lengths to get rid of a mouse.

Karen introduces Will and Grace to the new love of her life, Phil. But Will and Grace become increasingly suspicious that Phil has sinister intentions for their friend. 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 become convinced Karen is in danger when her new boyfriend, Phil, takes her to a cabin in the woods. With the help of Karen's assistant, Friday, Will and Grace race to save her. Jack makes up a story to a snobby reporter in order to keep his new bar relevant after its previous owner, Miss Coco Peru, steps down.