When Jen and Greg hire Clementine as a part-time nanny for Lark and invite her to join them for dinner, the waitress mistakes Jen for Lark's grandmother. Also, Tyler's new girlfriend turns out to be Sophia's fourth grade teacher, John hires a questionable company to set up an escape room in his house, and Matt grows frustrated with Colleen when she blames a valet for stealing her lottery ticket.

When Jen is offered a custom painting as payment from a hot new artist, she is thrilled until she sees the final product. Also, Sophia convinces Matt and Colleen to use her idea for a children's book but it isn't a new concept; Tyler and Clementine advertise their tiny house as a rental property; and John and Joan fall prey to a sleazy IRS scam.