Larry after watching Jeopardy decides to try and get his high school equivalency. So he asks Dick to help him. When he fails the test, Dick goes to the teacher and convinces him to give Larry another try and to test him as if he was on Jeopardy. And Joanna upon seeing the Inn's rating in the Vermont guide go down, sets out to restore it. So she drives George and Stephanie crazy.
Stef and Michael plan to go to Morocco when Stef and Joanna become best friends. Stef wants her and Dick to go too. Dick was there in the Army and got sick from the food and doesn't want to go, but Joanna talks him into going.
Dick was a member of a band in college and he plans a reunion with his other band members at the Inn. Everyone is now older, taking pills for all sorts of ailments due to getting older, but they try to perform anyway.
Everyone gets the measles and Stef ends up taking care of them while Michael can only talk to her through the front door of the Inn or by phone. George runs such a high fever that Stef calls the doctor to come in an emergency.
When the previous owners of the Stratford Inn become jealous of the inns new success, they try to scare everyone into thinking the Inn is haunted in hopes of getting the Loudens to sell the Inn back to them.
Michael balks when Mr. Vanderkellen demands he sign a prenuptial agreement, feeling it indicates a lack of trust on Stephanie's part. Meanwhile, Dick breaks an irreplaceable music box given to the Vanderkellens by Winston Churchill.