Grace comes home from a great date and listens to a staticy message she's received from Leo. Grace hides the message from Will, but when Will learns about it, he decides to take Grace to the Berkshires to get her mind off of Leo. Meanwhile, Karen and Jack try to set each other up.
|Karl T. Wright||Guest Star|
|Christian S. Anderson||Guest Star|
|Harry Connick Jr.||Guest Star|
|Patrick Fabian||Guest Star|
|John P. Connolly||Guest Star|