When Grace feels that Will is abusing his power as president of the tenant's association, she runs against him. Karen tries to buy back Jack's forgiveness when she lets his beloved bird, Guapo, fly out the window.

A sports-challenged Will tries to impress his new friend Matt – a sportscaster – with his athletic skills by checking into a batting cage but it takes Grace to show him how to improve his swing. Meanwhile, Grace is given a mission: impossible when Jack and Karen ask her to exotically re-decorate Jack's apartment.

When Grace frets that she and Will might drift apart like their similar friends, she impulsively buys an expensive piano which she hopes will cement their mutual bond and love for music – or at least give her an excuse to perform a lot of show tunes. Meanwhile, when Jack is dumped by his latest romantic interest, he vents his grief by writing trashy novels which instantly draw Karen's passionate attention.

Grace gives romantic advice to her slovenly new neighbor, Nathan, in hope of reuniting him with his girlfriend so he will move away. Meanwhile, Will and Jack are out on the town with an unwelcome chaperone: Karen's oblivious mother-in-law.

Will and Grace elect to disagree when it comes to choosing sides during a mayoral election; she supports the female Jewish candidate and he's voting for the gay nominee. To settle matters, the roomies host fund-raisers attended simultaneously by both aspirants.

Will attempts to sneak Leo back from Africa to surprise Grace for her birthday. But things don't quite go as planed. All starting with when Grace runs into Leo who arrived a little too soon. But, to spare Will's feelings, they agree to act like they never saw each other. Grace asks Karen and Jack to keep Leo busy until her ""birthday surprise."" Unfortunately, the duo takes their mission too seriously.