Hoping to cheer up Grace, a well-dressed Will takes his best friend with him on a dinner date. When the date stands him up, Will catches the eye of a female patron while Grace bumps into a guy with whom she once shared an ordinary, forgettable romantic encounter. Meanwhile, Karen takes student nurse Jack out to celebrate his school "success" but the evening turns sour when Karen runs into her ultimate nemesis, Candice Bergen. The meeting sparks yet another round in the Bergen/Walker Prank War of 2003.