When one of Eddies single idols comes for a visit, Eddie is in awe, while Joy is unimpressed by Webbys (guest star Ted McGinley) lifestyle of wild adventures and exotic travels. To Joy, Webby is running away from the one thing that can make him truly happy: a committed relationship. Ignoring Eddies warnings, Joy sets Webby up with Denise (guest star Tricia Fisher), who tames Webbys ways. When Webby is ready to settle down, Denise lets Joy know that shes not interested. Meanwhile, Jeff is miserable at the sight of his crying wife in an incredibly ugly shirt. Later, summer vacation has begun and Allison (guest-star Krysten Ritter) surprises her parents when she brings Doug (guest-star Tim Sharp) home. When Allison and Doug spend their days enjoying the summer, Steph convinces Eddie to join them. Meanwhile, Jeff and Joy feel left out and annoyed by their partners happiness but finally get convinced to join in.

To avoid doing housework with Joy, Eddie signs up to be a volunteer for a "Big Brother" program but things go awry when he's accidentally given an adult instead of a kid to mentor.