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

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 LA to Nashville and knows that Scoot’s desire to get married might be too much, too soon. Britt takes things further with PJ, but takes two steps back when she finds out her ex-boyfriend, Jon is seeing someone new.

Kristin Cavallari balances work, family, and friends and opens a new UJ store in Chicago. Relationships are challenged in unexpected ways, as Kristin and Jay Cutler redefine their inner-circle of friends, their marriage and the roots of happiness.

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 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'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.

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.