Watch Very Cavallari

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 perfect. After an emotional year, Brittainy struggles to find direction in her personal life and her career with Uncommon James. Meanwhile, marriage is on Justin's mind.

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 country-side, having a fabulous time along the way. But conflict erupts when a drunken Justin starts flirting with another man, causing Scoot to question their entire relationship. Meanwhile, back in Nashville, Brittainy has an unexpected breakdown when going to get her tattoo of Stone's band removed. Maybe she's not as over her ex as she thought.

Kristin travels to Tuscany to get in touch with her Italian roots and meet long-lost relatives for the first time. She brings Jay along as well, making plenty of time for epically romantic adventures. Meanwhile, back in Nashville, Brittainy attempts to move on from Stone once and for all.

Kristin and Jay take their friends on a wildly hilarious camping trip. Jay is right at home in the wilderness, while everyone else feels like a fish out of water. Meanwhile, Brittainy makes a serious error at the office, which quickly spirals into a major issue for Uncommon James.

Kristin embarks on another glamorous trip to Los Angeles for the Emmys, bringing Jay along as her LaLa Land sidekick. Meanwhile, Stone resurfaces in Brittainy's life, causing her to question everything about her new relationship with PJ.

Kristin takes off to Mexico for her first ever huge Uncommon James National TV Commercial Shoot with Brittainy, Pip and Jack in tow. Heidi and Audrina fly to Nashville to reminisce about their time on The Hills, reconnect and bond over the downfalls of trying to figure out who they can trust being in the public eye. Justin and Scoot move into their new house and struggle with the next steps in their relationship. Rubber meets the road when Scoot's mom and brother come to town.

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.

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 ASAP, but the contractors are unsure if they can meet her sky-high demands. Back in Nashville, Justin and Scoot go house hunting and sparks fly between Brittainy and a new flame.

While trying to balance work and family, Kristin mourns her failed friendship with Kelly and seeks advice from an astrologer that specializes in relationships.

Kristin heads to Chicago to meet up with her friend Biegs and check out spaces for a potential second UJ store, but is on edge about finding out if she's going to get her dream space or not. Justin's boyfriend Scoot arrives, and Brittainy deals with the aftermath of dumping Stone. Jay tries to show Justin and Scoot the ropes of Nashville life, and Justin sits down with Kelly to try and help navigate the conflict between her and Kristin.

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's also struggling.

It's Christmas-time in Nashville and Kristin and Jay find themselves with conflicting opinions on how to decorate their house for the holidays. This year, Kristin wants to throw the biggest holiday party that Uncommon James has seen, complete with a surprise musical guest, and recruits Brittainy and Colby to execute it to perfection. Meanwhile, Jay has something up his sleeve as a holiday surprise to Kristin.