As Cassie and Sam prepare to celebrate their first wedding anniversary, Cassie welcomes Grey House guest Joy, who seems to be spying on the Merriwicks.
Cassie helps Joy mark her mother's birthday by planting a tree and discovers a time capsule that Grace buried years ago; Sam competes against Middleton favorites in a chili cook-off.
Cassie, Abigail and Joy browse an estate sale, where Joy hopes to find a clock for Martha's renovation; Stephanie's ex-husband, Wes, comes to town to pack up their shared cabin.
Martha fills in as the local Dear Debbie advice columnist, getting an anonymous letter that adds intrigue to a progressive dinner attended by all the Middleton couples.
Cassie pursues a temporary art history professorship while Sam diagnoses Adam; Abigail and Donovan realize that the missing diamond from the Middleton treasure may help break the curse.
Sam successfully operates on Adam but not without complications; Joy, against Cassie's advice, dreams that Abigail and Donovan break up, and she tries to stop it from happening.
Cassie and Martha smudge the mayor's mansion in preparation for her housewarming gala; Abigail and Donovan decide to reunite and put up a final fight against Merriwick-Davenport.