Kristin's business is booming, with brand new Uncommon James offices, a wildly growing staff, and massive plans for expansion; Brittainy's work life's going great, but her relationship with Stone is on the rocks.
Kristin heads to Chicago to meet up with her friend Biegs and check out spaces for a potential second UJ store; finding out if she's going to get her dream space or not, however, has her on edge.
Kristin still mourns her failed friendship with Kelly; Brittainy is newly single, but is shocked when she is late getting her period and fears that she might be pregnant with Stone's baby.
Kristin heads back home to Chicago to visit her mom and check on the progress of her new retail store; time is ticking and Kristin wants to launch the store, but the contractors are unsure if they can meet her demands.
As her company grows, Kristin struggles to find a work-life balance and feels pressure to take a step back, while Jay has his sights set on bringing some mini donkeys to the farm; Justin begins to fear the leap from L.A. to Nashville.
Kristin takes off to Mexico for her first ever Uncommon James National TV commercial shoot with Brittainy, Pip and Jack; Heidi and Audrina fly to Nashville to reminisce about their time on "The Hills," and try to figure out who they can trust.
Kristin embarks on another trip to Los Angeles for the Emmys, bringing Jay along as her LaLa Land sidekick; Stone resurfaces in Brittainy's life, causing her to question everything about her new relationship with PJ.
Kristin and Jay take their friends on a camping trip; Jay is at home in the wilderness, while everyone else feels like a fish out of water; Brittainy makes a serious error at the office, which quickly spirals into a major issue for Uncommon James.
Kristin travels to Tuscany to get in touch with her Italian roots and meet long-lost relatives for the first time; Jay tags along as well, making plenty of time for romance; in Nashville, Brittainy attempts to move on from Stone once and for all.
Kristin and Jay's friends show up in Italy and bring the party with them; the crew embarks on a wine-fueled romp through the Italian countryside; conflict erupts when a drunken Justin starts flirting with another man.
The stakes are high as Kristin launches her second retail store in Chicago; it's a huge moment for Uncommon James, and Kristin needs every detail to be absolutely perfect; after an emotional year, Brittainy struggles to find direction in her life.