Kendall sets Kimmie up with one of Richard's dorky old school friends, James. But as Kimmie slowly warms to James on a double date, Richard has a surprising reaction. Meanwhile, Dan, Benji and Ruby temporarily move in with Kimmie and the gang, and slowly begin to drive the ladies crazy.

After they fail to get any interest from an Internet dating website, Kimmie takes it upon herself to embellish her profile and those of her friends.

Kimmie and the gang decide to attend a seminar by Jane Spencer, “The Love Lioness,” a relationship guru who likens finding men to hunting prey in the wild. They try her theories out at a hotel bar. It works a little too well when Kimmie picks up Parker and isn’t sure what to do when he invites her up to his room.

Richard reluctantly drives Kimmie, Marika and Helen-Alice to a remote cut-your-own Xmas tree lot upstate, but the trip over the river and through the woods goes terribly wrong when Marika gets them lost and they run out of gas… on Christmas Eve. They think they’re saved when they find a beautiful cabin miraculously stocked with a holiday feast... until the cranky old man who lives there shows up. Meanwhile, Kendall goes it alone with her frosty parents.

Kimmie gets a promotion that threatens a longs-standing tradition with her two best friends and roommates.

Kimmie, a junior attorney gets a big promotion at work. There she meets Richard, the son of the firm's senior partner, and is convinced that he is attracted to her. Kimmie starts to believe that life is starting to go her way, causing her friends Helen-Alice and Marika to worry that she may leave them behind.

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Kimmie plans to make a move on Richard at the office Halloween party. Kendall gets there first.

Kimmie gets new insight into her "frenemy" Kendall when the two end up together on an alcohol-fueled girls’ night out. Meanwhile, Marika and Helen-Alice go to the Murna Princess Warrior Convention and are shocked to find that their idol, Murna Princess Warrior (or rather Alison, the actress who portrays her), isn’t who they expected.

An alcohol-fueled night out leads to Kimmie gaining new insight about Kendall; Helen-Alice and Marika meet their idol.

Kimmie tries to convince a lawyer-hating rapper, Miss T, to sign with the firm; Miss T"s bodyguard takes an interest in Kimmie.

After breaking up with Richard, Kendall takes all of her anger out on Kimmie; Helen-Alice and Marika agree to makeovers.

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.

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.

After law firm big wig Porter Warner advises Kimmie to act more professional, she starts calling herself "Kimberly" and looks to Kendall for advice. But friends Helen-Alice and Marika fear that the new and improved Kimmie may be too cool for their 10th annual Cookie Prom, a celebration of their disastrous high school prom.

Kimmie celebrates her first Valentine's Day with a boyfriend but work intervenes, and later, Richard sends her mixed messages about their relationship. Marika gets a different message of her own when new friend, Frankie, hits on her and Kendall hosts a sex toy party in honor of the holiday.

When James breaks up with Kimmie after learning that Richard kissed her, Kimmie must decide which man she really wants; the firm is in chaos as everyone tries to find out who is getting a big promotion; Marika struggles with coming out.