June receives her 1 year roommate evaluation from Chloe, in which she is shocked to find that she has been given a D. She eventually realizes that the only aspect in her life that she could possibly be slacking off in is her love life. Luther sets her up with James' agent's assistant, Will. The two really hit it off and bond over having to deal with a crazy person in each of their lives. For June, it's Chloe and for Will, it's one of his clients, Chris Spalding, a demanding novelist. It is soon revealed that Chloe is Chris Spalding. After attempting to share this information with Will, June's plan backfires and Chloe has Will fired. June turns to James, who desperately needs Will's help on his own projects, to help get his job back. During this time, James is struggling to land an audition for a new Woody Allen film "Monte Carlo, Monte Carla."