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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.

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 La La 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.

Barney meets Bob Barker and gets to play in the Showcase Showdown on "The Price Is Right.".

When Marshall and Lily's wedding is not as they had envisioned it, Barney tries to salvage the special day.

At Marshall and Lily's wedding, Barney discovers that Ted and Robin have a secret that they have been hiding for weeks.

When he sees Robin with an Argentine lover (Enrique Iglesias) by her side, Ted decides he is ready to hit the town with Barney.

Barney and Ted decide to pose as out-of-towners in hope of getting the same female attention Robin's Argentine friend (Enrique Iglesias) receives.

Two beautiful women show Ted that they are very attracted to him; the gang helps Ted realize that bad luck does not always come in threes.

When Robin begins to date a single father, she bonds with his young son.

Ted's new girl is jealous because the story of how Ted met his friends is better than the story of how he met her.

Marshall gives up his dream of saving the Earth in favor of money after being courted by a lawyer (John Cho) from a corporate firm.

Marshall learns Lily's dirty little financial secret when he and she decide to buy an apartment.

When Ted thinks he has met a wonderful woman, the gang points out a deal-breaking flaw.

Lily and Marshall celebrate their first Thanksgiving as a married couple; Barney awaits the consequences of a slap bet.

Barney gets an invitation to the Victoria's Secret Fashion Show after-party, where he can mingle with all the models.

Ted's friends try to convince him that he should not date his doctor by sharing some of their own toxic experiences.

Ted emulates Barney and lives like there is no tomorrow, forcing Marshall to deliver a post-St. Patrick's Day reality check.

When Ted romantically pursues his beautiful dermatologist, Stella, he ends up attracting the attention of her assistant (Britney Spears).

A mystery woman sabotages Barney's love life, and to try to figure out who she is, Barney creates his own set of tournament brackets to decide which of 64 women has the most cause to hate him.

Marshall questions his decision to take a job in a corporate law firm after his boss emasculates him verbally.

Barney, in his own inimitable style, picks up the pieces when Robin picks up where she left off with an old flame, only to have him break her heart again.

When Barney breaks the "bro code," he struggles with the consequences of his actions.

Prompted by her popular best friend to spill details of her boring weekend, Olive, a clean-cut teen, decides to spice things up by telling a little lie about losing her virginity; when the high-school busybody overhears the conversation and spreads it all over campus, Olive is suddenly notorious but for the wrong reasons.

Eliza is smart and independent, but after years of bad boyfriends, Eliza finds herself newly single, jobless, and questioning all her decisions. Throwing caution to the wind, Eliza follows her best friend, Sofia, to the Hamptons and decides to change her approach to romance. They're going to follow the rules of dating from a 50-year-old self-help book.