A dashing doctor (Harry Connick Jr.) on horseback rescues Grace; Karen debates cheating on her imprisoned husband with hot-blooded suitor Lionel (Rip Torn).
Stalking Kevin Bacon (guest starring as himself) pays off for Jack when he is hired as the actor's personal assistant; Will and Grace pursue parenthood. Harry Connick Jr. and Rip Torn also guest star.
Smitten with the handsome doctor (Harry Connick Jr.), Grace stalls for time to reconsider having a baby with Will.
Grace schemes to hook up the mistress (Lesley Ann Warren) of Will's father with another man in order to break up the relationship.
After rediscovering a handsome high-school friend who's doing time, Grace dreams of their life together outside the Big House.
Grace reveals her ex-boyfriend's faults to his bride at the wedding rehearsal; Elliot's mother (Rosie O'Donnell) demands that Jack never see him again.
Will and Grace try to find more expansive digs despite the efforts of Sandra Bernhard; Jack stumbles across Karen's lowlife mother (guest star Suzanne Pleshette).
Moving into their new dream apartment makes Will and Grace homesick; Jack tries to reconcile Karen with her grifter mom (guest star Suzanne Pleshette).
Will presents his newly reconciled parents (Sydney Pollack, Blythe Danner) with a cruise for their anniversary, but their individual secrets ruin his hopes.
Will salvages a cherished garden gnome in the aftermath of his parent's divorce; Jack's afraid of being typecast as a straight man.
When Jack works instead of taking his son to a basketball tournament, he learns from Will that he missed his son's first kiss with a girl.
When the bride-to-be gets sick, Will persuades Grace to help plan the wedding for his visiting friends.
A detective (Michael Douglas) helps Will search for his stolen computer; a crazy neighbor (Molly Shannon) opens a business and prospers by stealing Grace's ideas.
Will takes Grace to have her picture taken after he wins a sitting with an eccentric celebrity photographer.
Will wants Grace to be the mother of his baby; Jack and Karen are inspired to pursue their own goals.
Will and Grace vacillate on artificial or natural means of conceiving a baby; Jack receives career advice from his show-business idol, Cher.