Ep 5. Grace 0, Jack 2000

In Will & Grace season 3 episode 5 titled "Grace 0, Jack 2000," we see Grace struggling with the realization that she has never had a satisfying romantic relationship. Jack, on the other hand, is celebrating his 2000th date and is convinced that he is a bona fide expert on relationships.

Grace feels like a failure in the romance department and seeks advice from Karen. Karen, however, advises her to embrace her independence and not let her love life define her. Meanwhile, Jack offers to set up Grace with one of his many ex-lovers who he believes is perfect for her.

The date doesn't quite go as planned and Grace ends up having a heart-to-heart with Jack about her fear of ending up alone. Jack surprisingly understands where Grace is coming from and reveals that he has never been in a fulfilling relationship either.

In the end, Grace decides to take Karen's advice and focus on herself while Jack realizes that he needs to stop searching for love in all the wrong places. The episode ends with a hilarious scene where Jack imagines himself as a contestant on The Bachelor and is disappointed to find out that he is the only contestant.

"Grace 0, Jack 2000" is a heartfelt and funny episode that explores the complexities of modern relationships and the importance of self-love. The chemistry between the cast is as magical as ever and the writing is sharp and witty.

Overall, Will & Grace season 3 episode 5 is a must-watch for fans of the show and anyone who enjoys a good laugh and an even better message about the power of self-acceptance.