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.

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.

Grace is horrified to realize that she's dated three men from the same family. Will and Karen get on each other's nerves at the office until they bond over watching -- and producing -- their own little telenovela.

Grace's father and Will's mother end up making a surprising and upsetting connection. Jack rebounds from his breakup with a new love. Karen must decide between her husband and her lover.

Will and Jack try to date younger guys but find it challenging. Grace and Karen experience a crisis that reveals Grace's true feelings about Karen.

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.

Grace's accidental run-in with Noah, a curmudgeonly man she follows on Twitter, hints at a possible new love interest. Jack wants to look younger before meeting Estefan's family on Skype but makes a terrible first impression after overdoing the numbing cream before his facial procedure. Meanwhile, Will helps Karen protect the intellectual property rights of her most prized possession.

Will and Grace try to convince themselves they are okay with dating the same man; Jack and Karen get an annoying commercial jingle stuck in their heads and must seek medical attention.

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

When both of their boyfriends ask to move in, Will and Grace use each other as an excuse to get out of it. A snowstorm traps Karen at the office and Jack in an elevator, where he reunites with old flame Drew and tests his commitment to monogamy.

Grace tries for her biggest job yet: decorating a string of boutique hotels for an obnoxious mogul. Will is surprised at his reaction to making Senior Partner. Beverly Leslie discloses his secret to Karen. Jack owns half of a winning lottery ticket.

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.

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 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.

Will is determined to not reminisce about his life in the city or his ex. Grace has false alarms of going into labor. Karen attempts to get closure with her ex-husband. Jack's dream of taking a bow on a Broadway stage becomes a very real possibility.

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 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.

Grace and her neighbor, James give their romance another shot – even after she slept with his son and his father. But an embarrassing incident puts Grace’s relationship, and her dignity, in jeopardy. Will decides it’s time for Jack to grow up, and cuts him off financially. But unlikely wisdom from Jack’s husband, Estefan, makes Will reconsider.

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.

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.

Despite her history of transgressions, Grace and her neighbor, James, decide to give their relationship one more shot. But when James invites Grace to his job at the aquarium, she endangers his job and a species. In order to help Will deal with his anxiety about becoming a father, Jack takes him to an unexpected place to blow off steam – church. Karen finds herself in a confessional booth, and a visit from Smitty makes her reconsider their entire relationship.

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.

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.

Will and Grace get competitive over whose process of having a baby is more difficult. Jack helps Karen prove to Danley Walker that she'll be a competent owner of her new baseball team. But Karen realizes that an old acquaintance, Amy, may be the help she really needs.

Jack helps Karen sneak into the manse to retrieve her coveted ring, but they're shocked to find it on the hand of Stan's new girlfriend, Val. While hosting Will's surrogate, Jenny, for the weekend, Will and Grace become the old folks they swore they'd never become.

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.

When Will's surrogate, Jenny, tells Will their relationship needs boundaries, Will ropes newly-out Dr. DiLorenzo into going on a fake date so he can spy on Jenny. Unsure if having a boy or girl is more difficult, Grace struggles with popping her gender reveal balloon. During her baseball team's championship game, Karen is torn between celebrating with Friday, and helping Jack build his confidence for a Broadway audition.

Will convinces Grace that her boyfriend, Noah, isn't in the wrong by refusing to let her meet his daughter, Katie. When Grace goes to apologize to Noah, she unintentionally meets Katie. Meanwhile, Will's mom, Marilyn, visits after the death of her beloved dog, and becomes upset when she doesn't get the emotional support she expects from her son. And Jack gets into an argument with his rec center boss, Theo.

When Will discovers Karen's estranged stepdaughter Olivia is a student in his law class, he attempts to solve their issues with a mock trial. Grace and Jack go on a diet together, but giving up their eating habits proves harder than anticipated.

Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man. Jack gets permission from his husband, Estefan, to sleep with his celebrity hall pass, Ryan Phillippe. Karen struggles to adapt when her assistant, Friday, books them on an economy flight.

Will and Grace's plan to win over Will's new Columbia department head goes awry when he drops dead in their apartment - and they use his phone to text his full recommendation of Will. Karen and Estefan's dislike for each other puts Jack in full damage control mode when he must keep them separate at his birthday dinner.

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.