After receiving the perfect gift from Cassie on their anniversary morning, Sam feels the pressure to reciprocate with a meaningful token of his love. Martha enters a bidding war with her nemesis Dotty for the new mayor’s mansion, which once belonged to a Davenport. Stephanie and her business partner butt heads about their food truck. Abigail and Donovan receive "misfortunes" in their fortune cookies that lead to both an unexpected discovery and more information about their families' curse. Meanwhile, Cassie hosts a guest at Grey House who hides her mysterious intentions for visiting Middleton.

When Sam finds himself without a crucial ingredient for his chili as the competition nears, he starts a chain of bartering that includes Martha, Stephanie and Abigail. Martha receives unexpected competition in her once-uncontested run for re-election and may have to put her stubbornness aside to compromise with her potential political adversary. Stephanie looks to lessons from her past to help a friend's daughter with her friendship woes. Abigail inadvertently reveals a secret about her father when she meets his new girlfriend, and his deception makes her worry about her own relationship with Donovan. Meanwhile, Cassie unearths a time capsule that reveals information about her current Grey House guest’s family -- and her own .