Kevin and his friends are venturing into adolescence as they find themselves staring at "Marsha Millany" in a bikini at the town pool. Winnie and Kevin survive a summer of "cross-town romance", Wayne has a car, and no one likes his new girlfriend Angela (Meredith Scott Lynn). To bring the family closer, Norma suggests going to Jack's company picnic on Labor Day, but the outing isn't as fun as they remember. Kevin finds out that the "office clown", Harry "Dead Wood" Detweiler (Rick Hurst) beat his father out of a promotion and is now NORCOM vice president while boating with his daughter Mimi (Soleil Moon Frye). In the softball game, Jack gets knocked out when Kevin accidentally hits a ball at him, but he is the one apologizing for not telling his son about the promotion. Wayne quickly gets dumped by Angela and wonders why. However, the family comes together in the end when they see Karen off to college.