When they are asked to read at the civil union of two friends, Will and Grace verbally spar over her self-serving, get-and-take attitude where Will is responsible for everything -- but what's really bugging him is the overwhelming feeling that Grace is behaving more like a wife than an old friend. Meanwhile, Karen tries to help a caffeine-addicted Jack get over a failed crush but he's so jacked-up on Java that only a tough-love approach will work.
Will and Grace get carried away in an escrow undertow when they pose as a wealthy couple shopping for homes of the rich-and-famous and visit Sandra Bernhard's posh townhouse where they become fast friends and make an fake offer -- but their ploy fizzles when she accepts their offer. Elsewhere, Karen is forced to attend her young stepson's swim meet and is uncharacteristically chastised by another mother for arriving late while Jack begins attending Co-dependents Anonymous meetings.
Will wanting to impress his new boyfriend who's a sport enthusiast asks Grace to teach him about sports starting with hitting a ball which he does terribly. Jack and Karen asks Grace to decorate Jack's apartment and initially they're difficult when she makes her proposal. But when they see a phony letter Grace made to get out of jury duty which states that she's mentally unbalanced, they give in to her demands not to upset her.
Will gets upset when his new boyfriend refuses to recognize him as his boyfriend when they're in public and introduces him as his brother. Grace tells him he should dump him but Will finds it difficult to do that. And Karen discovers that Stan is giving a portion of his estate to charity in his will.
Jack receives a letter that indicates he is black. Grace inherits an old a car from a deceased uncle. She sells the the car that she believes to be a lemon to a nun. Meanwhile, Karen discovers that Rosario is moonlighting for Beverly Leslie. Grace realizes that she should have kept the car and tries to buy it back.
Will is dating a guy who is not exactly attractive because he is fond of his dog. Will takes care of the dog while he's away and when Jack loses him, Will doesn't know what to do. Grace meets Karen's nephew and she keeps Grace from dating him by telling lies. Grace thinks Karen doesn't think she's good enough for him.
Will and Grace play poker with Larry, Rob, and Joe but because of certain annoying habits, the guys want Grace out and tell Will he has to tell her. Will tells her and she tries to change, when she does, she tells Will what she's doing. Karen wants to have plastic surgery but she wants to see it done on someone else first. So she gets an acquaintance to have the procedure first.
Graces fears Will is pulling away, so she buys a piano for them to bond over. Meanwhile Jack is depressed over a recent breakup and channels his energy into writing roman novels, which Karen quickly becomes addicted to.
When Will, Grace, Jack, and Karen want to spend Thanksgiving together. But they each have to visit someone or go to another Thanksgiving dinner. So Will comes up with the plan to visit each place for one hour at a time. But each visit leaves them reeling and leaves them unable to enjoy their own celebration.