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Kimmie is torn between Richard and James (Nate Torrence); a visit from Richard’s dad (Charles Shaughnessy) throws the firm into chaos; Marika struggles to find a way to tell her friends she’s gay.
Kimmie tries to celebrate her first Valentine's Day with James, but work gets in the way and Richard sends her mixed messages; a new friend hits on Marika; Kendall has a sex toy party.
A law firm executive convinces Kimmie she needs to act more professional, but Helen-Alice and Marika are fearful of her new attitude.
When a visiting ex causes Richard to fall off the wagon, Kimmie and Kendall work together to help him; Ruby and Marika have a misunderstanding.
Helen-Alice and Marika are jealous when Kimmie starts spending a lot of time with her new boyfriend; Kendall feels lonely after her breakup with Richard.
After her break-up with Richard, Kendall takes her anger out on Kimmie, and the firm’s head of HR (guest star Fred Armisen) is called in to broker a truce; Helen-Alice and Marika agree to makeovers.
When Kimmie invites James to a dinner party, her neighbors Dan, Benji and Ruby volunteer to cater, and Jazmine and her husband show up drunk.
Kimmie tries to convince a lawyer-hating rapper, Miss T, to sign with the firm; Miss T's bodyguard takes an interest in Kimmie.
Richard reluctantly agrees to drive Kimmie and her friends to a cut-your-own Christmas tree lot upstate, but their trip doesn't go as planned; Kendall spends the holiday with her frosty parents.
Kimmie thinks back to how her big promotion at the firm changed her life and gave her the confidence to convince best friends Helen-Alice and Marika to forgo their standing “Super Fun Night” tradition.
Kendall sets Kimmie up on a date with one of Richard's nerdy friends, which elicits a surprising reaction from Richard; Kimmie and her roommates go crazy when Dan, Benji and Ruby move in temporarily.
Kimmie and her friends attend a seminar by a relationship guru (Molly Shannon); Kimmie uses some of the guru's tips and picks up a guy (Will Sasso) at a hotel bar.
An alcohol-fueled night out leads to Kimmie gaining new insight about Kendall; Helen-Alice and Marika meet their idol, Murna Princess Warrior (Brooke Shields).
When Kimmie's mom Pamela (Jacki Weaver) takes over planning Jazmine's engagement party, she gives it a luau theme and a bathing suit dress code.
Kimmie decides to take advantage of the office Halloween party to don a sexy costume and tell Richard how she feels; the guys from Kimmie's building invite the girls to a party.
When Kimmie embellishes the girls' online dating profiles, they end up on a group date trying to maintain their lies.
Kimmie's eagerness to try new things flags when she learns the next destination is a piano bar; Kendall decides to do something about Kimmie and Richard's friendship.