Type-A June is operating at her highest potential when she lands a demanding internship, juggles two jobs and adds on more responsibilities. But she meets her match when she's tasked with cleaning up one of Chloe's incredibly irresponsible, half-baked ideas. Meanwhile, James is psyched to have landed a classic body-swap movie, co-starring the talented Kiernan Shipka, and dives head first into the research.

Halloween is June's favorite holiday, and even more so this year now that she is single! However when she discovers that Chloe plays elaborate Halloween "tricks" every year, June becomes consumed with stopping her before Chloe really hurts someone she might actually care about. Meanwhile due to a deep-rooted childhood fear of Halloween, James throws his annual Halloween "Positivity" Party.

June is making a real effort with Chloe to become BFFs, but Chloe is very wary because girls can be catty and manipulative, so instead June befriends a group of girls at her Pilates class who are the epitome of what Chloe detests. Meanwhile, James decides it's time to beef up his public image again and signs up to mentor an at-risk kid, but when they meet, neither of them knows what to do with the other.

June discovers that Chloe has been attending Alcoholics Anonymous Meetings, to share her crazy partying stories as well as take free booze from the alcoholics. Pepper sets Mark up on a date with one of her friends, and June struggles to hide her jealousy. Meanwhile, James learns that he is on the short list for Woody Allen’s film “Monte Carlo, Monte Carla” but he may not get the role because Woody does not think he is deep enough.