Kristin and Jay have moved into their new home and have expanded their farm life family with chickens and goats. As a surprise for Jay, Kristin agrees to babysit her friend Caroline Bryan's llama. Meanwhile, Uncommon James is busier than ever.

Kristin balances business and pleasure as she heads to Palm Springs, Calif., for a campaign shoot; in Nashville, Brittainy struggles to take control over a massive shipping issue; Jay has a hard time with Kristin always being out of town.

As problems continue to arise at UJ, Kristin sends in Jay to observe the workflow at the office; Kristin considers bringing back a former employee, but emotions run wild when her decision doesn't sit well with the staff.

Kristin and Brittainy head to Los Angeles to open up an Uncommon James Pop Shop, while the staff back in Nashville are put to the test on Cyber Monday. Jay lends some dating advice to Kelly, and Kristin heads back to Laguna Beach to meet up with an old friend.

Kristin takes an emotional trip down memory lane as she wraps up her visit in Laguna; the mean girl culture at Uncommon James comes to a head; Chuy brings everyone together for his annual block party and sets Kelly up on a blind date.

Kristin takes off her boss hat when her friends come to Nashville, but everyone is left confused when Jay loses his cool; Brittainy tries to bury the hatchet with Matt; Kelly commiserates about dating in her 30s and considers freezing her eggs.

In the aftermath of the awkward friend dinner, Kristin and Jay realize they need to make more time for each other as a couple. Brittainy's new, close friendship with Kristin creates a rift between her and the other UJ employees, culminating in a confrontation with Reagan at the UJ holiday party. Meanwhile, Kelly branches out on a blind date and reconnects with an old flame.

Kristin and Jay make their way to Cabo San Lucas for some fun in the sun and to work on their relationship. Before they go, Kristin convinces Jay to host a Little James photoshoot at their house. Tensions between Reagan and Brittainy build up and cause a confrontational meeting.

Things heat up when Kristin's friends join Kristin and Jay on their sizzling Cabo vacation. Back in Nashville, Reagan struggles to find direction at Uncommon James after her explosive confrontation with Brittainy. Stone and Brittany clash over their conflicting relationship goals.

Kristin is thrown into the middle of Brittainy and Reagan's feud; Jay takes the next step toward a new venture with a business of his own; Stone pushes for commitment from Brittainy, but she spirals at the thought of marriage.

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.