Rushing to her own artificial insemination, Grace runs into a lamp post and is knocked out. She then meets a man, Leo, who rides a white horse. And asks her out. And is a doctor. And also Jewish. Meanwhile, Karen goes to return the room key to the man who mistook her for a high class prostitute, but ends up entering his room... Will discovers that having a baby means a change in priorities.
Jack is stalking Kevin Bacon. For real. Fortunately, Kevin Bacon is interviewing assistant applicants and Jack beats the others with his vast knowledge of Kevin Bacon. Jack's first assignment: to find Kevin's stalker! Grace takes her first pregnancy test. Karen is trying to break up with Lionel. Dr. Leo comes to see Grace at her workshop - but only to ask her to redesign his practice space.
Karen has to shower at Will & Grace's place because Stan froze all her assets, forcing Karen to live in her limo. Will's retired boss's business partner, Mr. Stein, arrives from the law firm's London office to "turn the company around". And he's quite upset because of the deficiencies of the firm's N.Y. office. And a little bit... eccentric.
When Grace accompanies Leo to dinner with some "friends," she doesn't realize that he's tricked her and instead introduced her to his real parents--and she soon regrets her earlier salty dialogue and suggestive attitude. Elsewhere, Jack is again confronted by Zandra, his gruff acting teacher, when he tries to showcase his meager talent in a class while a willing Will joins Karen in subjecting to a Botox facial injection.
Grace and Leo impetuously take their vows at a Central Park wedding that is a ratings stunt hosted by Today's Katie Couric. Grace's pals, especially Will, are hurt that they weren't invited, but all seems forgiven when everyone-including Grace's outspoken mom and the subdued Mrs. Marcus-gather days later for a swank reception. It should be a festive bash, but the emergence of unsettling details about Leo-and about the park nuptials-give Grace reason to wonder whether she has made a mistake.
After a displaced Karen is booted from her Palace Hotel digs, a sympathetic Will agrees to let her move in with him-at least until she turns his apartment into a federal disaster zone with her exorbitant lifestyle, forcing Will to try and unload her onto Grace's shoulders. Meanwhile, Jack loses style points when he poses incognito out of fear that the "Gay Mafia" has it out for him.
"On Christmas Eve, Grace is torn when she has only two tickets to "The Nutcracker" musical and can't take both her best friend Will and new husband Leo (Grammy-winning guest star Harry Connick, Jr.)- but her back-and-forth indecision leaves Will spinning like a Hanukkah dreidel between a dithering Grace and his previous holiday plans with Jack and Karen."
"When Jack convinces tangle-footed Will to join him on a gay soccer team, Will's inept playing leaves him warming the bench - which allows him to bond with the teenaged Elliot, who also is the last man called upon with his own youth soccer team. Meanwhile, Grace is delighted that Karen is giddy in anticipation of her date with a handsome restaurant owner (guest star Andy Garcia)."
Will and Jack are trying to teach gayness to Barry, because Karen is giving them $20,000 for it. Leo has an announcement: he has to leave for Africa because he belongs to Doctors without Borders. Later, in order to make Barry feel more at ease in a gay bar, Will recounts his first time in a gay bar, in the 1980s.
Barry goes on a date with Jack. Will is jealous and intrudes on their date. At Karen's hotel, her maid quits, and Karen puts on her apron just to show that she can manage without her. Then Karen just happens to bump into a handsome maintenance man who mistakes her for a maid. Smitten, Karen switches roles with her maid in order to get to know the man. When Grace doesn't hear from her for three days, she goes to see what's going on and ends up advising Karen with her dilemma.
Will, Karen and Will's boss Mr. Stein (Gene Wilder) form an anti-romance club thanks to Will and his recent break-up with Barry. The three hold two meetings claiming that "love stinks" until Karen and Mr. Stein form a budding relationship. The two carry on having sex and dating behind Will's back not wanting to hurt him. Will breaks up the club after he finds out claiming that "If you're going to form a club for people who are alone and bitter, you have to at least stay bitter."Meanwhile, Grace decides to make a sexy video for Leo who is away in Africa. Jack wakes up ...
Grace's birthday is coming up and as the best surprise ever for Grace, who loves surprises, Will has flown Leo from Africa... and forgotten to factor in the time differential into the travel time. So Leo arrives one day early and Will has to hide him while Karen and Jack are tasked to keep Grace away from the apartment. Can they do that? Well, they are Karen and Jack.
Stan dies. Everyone goes to the funeral. Karen runs into Stan's mistress, Lorraine. Karen asks Will what did Stan leave her, he tells that Stan made some new changes in his will before his death. Karen fears that Stan is leaving his estate to Lorraine. When there's a heated exchange between the women, Karen tells Will to send for the will. And when it arrives, Will reads it and it's very long.
Grace has promised to go to Guatemala with Leo, but when Karen invites Will & Jack for a long cruise, she breaks down and Leo releases her from her promise. Grace then decides to join the others on their cruise. But then Leo's partner, Dr. Morty stops by. And it just happens to be that Dr. Morty is actually a stunning, busty blonde. And she's going to be working at the same place as Leo... Can Grace make herself trust Leo?