S1, E7: Kendall sets Kimmie up with one of Richard's dorky old school friends, James (guest star Nate Torrence – She's Out of My League, Mr. Sunshine). But as Kimmie slowly warms to James on a double date, Richard has a surprising reaction. Meanwhile, Dan (recurring guest star John Gemberling), Benji (recurring guest star Paul Rust) and Ruby (recurring guest star Dan Ahdoot) temporarily move in with Kimmie and the gang, and slowly begin to drive the ladies crazy.