Conscious Coupling -Will’s and Grace’s boyfriends, McCoy and Noah, ask them to move in, and Will and Grace use each other as their excuse to get out of it. Meanwhile, a snowstorm keeps Karen at the office, where she meets Nikki, a woman who works upstairs. The storm also traps Jack in an elevator, causing him to reunite with an old flame, Drew, that tests Jack’s commitment to a monogamous lifestyle.
Bad Blood -Grace’s dad, Martin, is rushed to the hospital with a bleeding ulcer, and Grace is shocked when he refuses to take Will’s blood for a transfusion. When Will’s mom, Marilyn, finds out, she uncharacteristically takes Martin to task. Karen’s demands for Jack’s wedding, along with upstaging him during his one man show, cause Jack to uninvite Karen from his wedding.
Supreme Courtship – Jack’s insistence that Will be nicer to his fiancé, Estefan, backfires when Estefan thinks Will is in love with him. In a hurry to buy her boyfriend Noah a Valentine’s Day gift, Grace unknowingly knocks over a prominent figure while going after a taxi. And when Karen discovers that Noah not only writes her favorite romance novels but also plans to kill off the main character, she forces him to rewrite the story.
The Real McCoy – 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.
The Pursuit of Happiness – Grace is enlisted by Malcolm to help him win back Karen’s affections. Will’s flirtation with his co-worker, Paul, takes a turn when details about Paul’s home life put Will in an ethical dilemma. And Jack’s run-in with Zusanna, the sister of his former acting teacher, reignites Jack’s passion for performing.
The Scales of Justice -Will discovers Karen’s estranged stepdaughter Olivia is a student in his law class, and 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.
Dead Man Texting -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.
Family, Trip -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.
So Long, Division – Will convinces Grace that her 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.
Anchor Away – Jack convinces Will to act silly and stupid in order to attract a handsome, gay TV news anchor with a pension for dim, frothy men. 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.
Kid ‘n Play – Will discovers that Noah has a child he hasn’t told Grace about, but is now sworn to secrecy. Karen and Jack’s relationship is tested when she fires him from the play she’s producing and replaces him with Jon Cryer.