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.

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.

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.

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.