Greg stirs up an old family feud when he finds money he accused Matt of stealing from him when they were younger. Also, Joan takes offense when Heather writes off her forgetfulness as "old age"; Colleen confronts a mechanic she believes is sexist; and Tim makes the kids go through an impromptu earthquake drill to see if they could figure out how to get home without money or cell service.

When Heather finds a map to a time capsule she buried with her brothers as kids, they all set out to find it and dig it up. Also, Jen learns she has a low car service rating so she books rides across the city to charm drivers and increase her score; Joan joins her neighbor's poker game in an effort to win an unusual prize; and John finally gets hearing aids but they aren't having the effect he was hoping for.

When Tim and Heather go to an expensive dinner to celebrate their anniversary, they are determined to finish every bite of their pricey 20-course meal. Also, Jen and Greg try to quickly potty-train Lark before her first day of preschool; Tyler gets jealous of the attention Clementine is getting at work; and Matt and Samantha team up for a “Middle Child Day” and go to a trapeze school.

When Heather tells Sophia she has to get rid of her stuffed animals, Sophia stages a musical with them to see if she can change her mother's mind. Also, Colleen babysits Lark, and Jen comes home to find her dolled up in Colleen's old pageant dress; Joan's bike is stolen from the driveway so she enlists Matt, Greg and Tim to join her in tracking it down; and Tyler and Clementine get John's help to sell their homemade beef jerky at the farmer's market.

When the Short family arrives at their vacation resort in the Yucatan, their accommodations aren’t quite what they expected. Heather is ridiculously overprotective of Sophia during the family activities. Jen and Greg discover that Matt and Colleen have been duping everyone. John and Joan get separated from their tour group in the jungle.