Will & Grace (1998)

Season 3: Episode 25

An exasperated Grace tries to mediate between a resentful Will and her sloppy, free-spirited boyfriend Nathan when Nathan moves in while Jack is in a royal dither as he plans to finally meet his unseen father face-to-face. However, Grace grows nervous when the two polar-opposite men find some common ground and she ponders how a devoted boyfriend might affect her equally important relationship with her longtime buddy Will. After settling his father issues, Jack later gets the surprise of his life in a most unexpected fashion.