Jack’s Big Gay Wedding – Jack and Estefan’s romantic wedding in Spain takes a detour when their flight is cancelled, forcing them to get married at the airport by their friend Miss Coco. McCoy’s big job offer in London has Will worried about engaging in a long-distance relationship. While dealing with doubts about her current relationship, Grace meets a charming guy at the airport who inspires her to make an impulsive decision. Advice from Smitty makes Karen reconsider her commitment to Nikki and her own orientation.
The Things We Do For Love – The morning after his bachelor party, Jack realizes he’s lost one of the thirteen gold coins he is to present to Estefan at their wedding so that their relationship will not be forever cursed. Although Grace denies it, Will becomes concerned that she is the only one compromising in her relationship with Noah. Karen makes it official when she shows up at Grace and Noah’s dinner party with her new date, Nikki.
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.