Confidants, best friends and roomies, Will and Grace make the perfect couple. Too bad he's gay and she's straight. What's a single New Yorker to do? Season 5 of the Emmy-winning sitcom finds Grace (Debra Messing) getting hot and heavy with a handsome doctor (Harry Connick Jr.). This development, unfortunately, leaves Will (Eric McCormack) feeling out in the cold. Guest stars include Gene Wilder, Macaulay Culkin, Minnie Driver and Demi Moore.

14. Homojo - Jack suffers Karen's wrath when he is seduced into friendship with her manipulative British romantic rival, who has set up house with Karen's ex-husband. Meanwhile, Will and Grace try to re-connect their lagging friendship with a competitive night of board games with their friends. 3.5 stars.

15. Women & Children First - Jack rehires his childhood babysitter, much to Will's chagrin. Meanwhile, at a girls' night in, Grace faces an identity crisis as a wife, and everyone's advice, except for Karen's. 3.5 stars.

16. Fagmalion Part Three: Bye, Bye, Beardy - As Karen battles Beverley Leslie at a silent auction at the Human Rights Campaign gala, Jack and Will unveil the new and improved Barry. But, as the transformation comes to an end, Will discovers that his feelings for Barry may run deeper than he thought. 4 stars.

17. Fagmalion Part Four: The Guy Who Loved Me - While Jack and Barry have their first date, Will interrupts to confess that he has feelings for Barry. Then Jack and Will give Barry an ultimatum: he must choose which one he would like to date. The decision is made - Will. At her hotel, Karen mocks Rosario by putting on a maid's apron. She is then mistaken for an actual maid by a very handsome maintenance man who has a disliking for the rich. In order to be near him, she and Rosario switch roles. After a week of perfect dates, Will tells Barry that he wants their relationship to be exclusive. However, Barry claims that he needs to play the field more and see what's out there before he settles down. 4 stars.

18. Sex, Losers, & Videotape - Will, Karen and Will's boss Mr. Stein (Gene Wilder) form an anti-romance club thanks to Will and his recent break-up with Barry. The three hold two meetings claiming that "love stinks" until Karen and Mr. Stein form a budding relationship. The two carry on having sex and dating behind Wills back not wanting to hurt him. Will breaks up the club after he finds out claiming that "If you're going to form a club for people who are alone and bitter, you have to at least stay bitter." Meanwhile, Grace decides to make a sexy video for Leo who is away in Africa. Jack wakes up to the sound of her singing and tells her that that's not sexy at all. He invites her to his acting class where the students are supposed to be very open to each other. Grace attends one class, but finds that it isn't helping one bit. Jack films her taking a shower without her knowing it. When she sees the tape, she agrees that it is very sexy only to find out that Jack has been sharing it with his class. 4 stars.

Disc 3: 3.8 stars
Season 5 (Disc 1-3): 3.87 stars
Collection (Season 1-4): 3.61 stars