Grace is dismayed to learn that her sisters have bailed out on their father's birthday party, and it's going to be just her and her parents. Meanwhile, Jack is excited about the project he's working on for Out TV and Will gets set up on a blind date.

Grace's true feelings are revealed when Will catches her holding onto a book in which she's pressed a flower that Leo gave her on their second date. Meanwhile, Jack is excited about appearing as Janet Jackson's sixth back-up dancer.

Grace is frustrated that she's lost another therapist. All that she wants from a shrink, she tells Will and Jack, is for him to fall in love with her so that she can reject him and restore her confidence.

Jack begins to crack under his bubbly exterior when his boss at Out TV shows him a clip of a show to get his opinion, and while Jack adores it, his boss thumbs his nose at the show. Jack develops an inferiority complex over lacking the college education and job experience of his coworkers.

With Grace having a particularly hard time forgetting about Leo, the whole gang decides to take a trip up to the Berkshires under strict instructions not to mention his name. However, even with an assignment from Out TV to keep him occupied, Jack still drags Karen into his irritating antics, and Will and Grace decide to take extreme measures to make the best of their trip.

Will doesn't have time for breakfast plans with his usual gang, because he's meeting Vince's mother for the first time, in preparation for Thanksgiving. Vince tells Will that she is already set on hating him, but will thinks he can win her over with a shopping trip.

The whole gang goes over to Vince's for Thanksgiving dinner, where Will is doing all the cooking because Vince's mom broke her toe. Vince's attractive cousin Sal ends up on the menu for both Grace and Karen, who fight over his attention the whole evening.

Grace finally overcomes the final stages of grief over her divorce when she checks out an attractive stranger's butt. Officially ready to get back in the game, Grace lets will set her up with someone from his office.

Vince seems down, especially when Will introduces him to people as his "cop boyfriend," but Will is too distracted to notice what's bothering him. Meanwhile, Karen is interviewed for Parade magazine, and the journalist sent to speak with her turns out to be an old classmate whose memories of Karen are less than positive.