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 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.