As Ed and Bonnie grow more comfortable in their relationship, Carol grows more uncomfortable so Ed suggests that they all go out for dinner. Not wanting to be a third wheel, Carol brings an escort along. But dinner is a disaster for everyone when a misundering with her escort forces Carol to betray Molly's confindence and Bonnie drops a bombshell on Ed: she's accepted a job in Washington, DC; Big Rudy, the former owner of Stuckeybowl decides he wants the bowling alley back and resorts to dirty tricks to get what he wants-even enlisting Phil's help.

In court Ed represents a singer/songwriter suing her band for the rights to her songs after she was kicked out.

A brush with death inspires a local man to change his life and do things he's never done before such as scale a wall, bowl naked, and go out with Molly. Meanwhile, Ed tries to recapture his youth by doing things he did when he was 18, and Warren becomes inspired by Thoreau's call to ""simplify"".

To ensure that Stuckeybowl outlasts him, Ed seeks to have it declared an historical landmark. Meanwhile in court, he reprresents a man overcharged for a placebo pill; Jeff causes friction between Molly and Carol.