| Season | Episode | Airdate | Episode Title | Story Line |
| 03.01 | 46 | 10/12/2000 | New Will City | Will returns from the Caribbean to discover Grace has a new best friend: Jack.
to Rosario being arrested for smuggling. |
| 03.02 | 47 | 10/19/2000 | Fear and Clothing | Will's apartment becomes a haven for Grace after a break-in attempt; Meanwhile, Jack and Karen aren't speaking. |
| 03.03 | 48 | 10/19/2000 | Husbands and Trophy Wives | Will and Jack are stunned when their favorite party-boy couple become dads; Karen fears losing her cushy position as Stan's trophy wife. |
| 03.04 | 49 | 10/26/2000 | Girl Trouble | Grace is appalled when her new intern suddenly emulates Karen and takes on her brass persona. Meanwhile, Will and Jack muck up a gay-sensitivity seminar for local cops. |
| 03.05 | 50 | 11/02/2000 | Grace 0, Jack 2000 | Grace finds it hard to call it quits with Ben. Meanwhile, Jack livens up his failing cabaret act at Will's expense. |
| 03.06 | 51 | 11/09/2000 | Love Plus One | A "Cyrano de Bergerac"-style plot has Jack borrowing Will's words to impress a crush, while an ex asks an amazed Grace to join him in a threesome with his new lover. |
| 03.07 | 52 | 11/16/2000 | Gypsies, Tramps and Weed | Will is terrified by a fortune teller's predictions. Meanwhile, pop icon Cher encounters her biggest fan, Jack. |
| 03.08 | 53 | 11/23/2000 | Lows in the Mid-Eighties | A crucial confession highlights Thanksgiving 1985, when college student Grace takes boyfriend Will home to meet her family. Meanwhile, a rare glimpse into Karen's past includes a string of lovers and Martina Navratilova. |
| 03.09 | 54 | 12/14/2000 | Three's a Crowd, Six Is a Freak Show | Will and Jack do battle over the same lover, while Grace has trouble accepting her new beau when she learns he has six toes on one of his feet. |
| 03.10 | 55 | 01/04/2001 | Coffee & Commitment | At Joe and Larry's commitment ceremony, Will chides Grace for mooching, while Jack and Karen have to give up their vices. |
| 03.11 | 56 | 01/11/2001 | Swimming Pools... Movie Stars | Will and Grace befriend Sandra Bernhard by posing as prospective buyers for her condo. Karen attends her stepsons swim meet. |
| 03.12 | 57 | 02/01/2001 | Crazy in Love | Will enlists Grace to help him improve his batting skills in hopes of impressing new friend Matt. Grace decorates Jack's apartment. |
| 03.13 | 58 | 02/08/2001 | Brothers, a Love Story | Will's romance becomes strained because Matt is still in the closet. Karen reads Stan's will. |
| 03.14 | 59 | 02/15/2001 | My Uncle the Car | Grace regrets selling her late uncle's old car to a nun and attempts to get it back. Karen catches Rosario moonlighting at Beverley Leslie's. |
| 03.15 | 60 | 02/22/2001 | Cheaters | Grace catches Will's father with a glamorous stranger. Karen thinks Stan is cheating on her. |
| 03.16 | 61 | 03/15/2001 | Mad Dogs and Average Men | Variations on the dating game find Will cold to a fawning beau and Grace hot for Karen's handsome nephew. |
| 03.17 | 62 | 03/29/2001 | Poker? I Don't Even Like Her | Grace ruins Will's weekly poker game; Jack and Karen target a plastic surgery guinea pig. |
| 03.18 | 63 | 04/19/2001 | An Old-Fashioned Piano Party | Grace buys a new piano to solidify her relationship with Will. Jack's juicy novel-in-progress turns Karen on. |
| 03.19 | 64 | 04/26/2001 | The Young and the Tactless | Grace attempts to get rid of her slovenly new neighbor. Karen dumps her mother-in-law on Will and Jack. |
| 03.20 | 65 | 05/03/2001 | Alice Doesn't Lisp Here Anymore | False assumptions vex Grace, who's attending the funeral of classmate she once tormented; and Jack, who's getting all dolled up for a gay cabaret awards event. |
| 03.21 | 66 | 05/10/2001 | Last of the Really Odd Lovers | Anxieties plague the romance between Grace and the annoying Nathan, and between Will and a much younger guy. |
| 03.22 | 67 | 05/17/2001 | Sons and Lovers | Grace tries to keep the peace between her slovenly boyfriend and a resentful Will; Jack plans to meet his father for the first time. |