Grace comes home from a great date and listens to a staticy message she's received from Leo. She thinks Leo is telling her happy anniversary and that he wants to meet on the top of the Peninsula Hotel as they had always planned. 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. However, after Karen gets paired with her gardener and Jack is set up with a straight, married guy, Jack and Karen decide they are the best people for each other.