June moves to Manhattan to follow her dream job and the most perfect apartment, but they both disappear in seconds after her arrival, thanks to a CEO from the Bernie Madoff school of embezzlement. Without anywhere to live or work, June seems to turn her luck, when she gets hired at acoffeeshop and meets Chloe, a charming, vivacious roommate but without any morals.
Dating is awkward enough, but when you add Chloe into the mix, it grows tenfold, which June learns the hard way when she begrudgingly allows Chloe to set her up. Meanwhile, James decides to teach an acting class but can't seem to escape his Dawson persona.
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.
Chloe takes it upon herself to teach June to be sexually empowered and to dabble in some casual encounters. However Chloe's own sex life catches up to her, and to James, when their old sex tape leaks out to the public and James freaks out on how this will affect his likability.
Finally feeling like one of the popular kids, June is desperate to keep pace with Chloe and her partying ways. It's not an easy task, especially when Chloe's 'it girl' lifestyle is so legendary that there's even a whole Japanese comic book series based on it! Meanwhile, James loses it when he discovers that Dean Cain's "Dancing with the Stars" dressing room is bigger than his.