Kimmie taps into her alter ego, "Lil' Big Kim," to convince famous rap artist Miss T - who hates all lawyers - to sign with the firm. Meanwhile, Miss T's bodyguard, Antwan, takes a shine to Kimmie when she ends up taking the whole gang to an exclusive club in an attempt to seal the deal.
Kimmie invites James to her place for a dinner party. What could go wrong? Lots, especially when neighbors Dan, Benji and Ruby volunteer their catering services, and sister Jazmine and her new hubby Jason show up very drunk.
After her breakup with Richard, Kendall takes her anger out on Kimmie - so much so that Brian Headfoot, the firm's frazzled head of Human Resources, is called in to broker a truce between them. Meanwhile, Marika and Helen-Alice agree to let Jazmine's vapid friends Heidi and Hayley give them a makeover at their new salon.
After Kimmie loses her virginity to James and the pair begin having sleepover dates, Marika and Helen-Alice feel miffed that their friend suddenly has no time for them. Meanwhile, Kendall, feeling a little lonely since her breakup with Richard, stoops to a new low - hanging out with Marika and Helen-Alice.
When Richard's hard-partying ex, Lucinda, turns up in New York City, they hook up and he falls off the wagon. Kimmie and Kendall team up to show Richard that Lucinda is a bad influence. Meanwhile, Ruby asks Marika out and she assumes it's a date. She's shocked when he tells her he just wanted a wing woman and he's always assumed that she is gay.
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. Meanwhile, 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.
Kimmie's boyfriend, James, breaks up with her when she admits that Richard kissed her. She's torn between trying to get James back or telling Richard how she really feels about him. Meanwhile, a visit from Richard's autocratic dad, Rupert Royce, throws the firm into chaos over who will be getting the next big promotion, and Marika struggles to find a way to tell her friends she's gay.