June moves to Manhattan for a dream job and the perfect company apartment, only to have them disappear in a puff of reality. It seems that her luck has turned when she gets hired at a coffee shop and finds Chloe, a charming, vivacious roommate - but with the morals of a pirate.

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.

June is devastated when she receives a wedding invitation addressed to her and her ex-fiance, so in an attempt make her feel better, Chloe gives June a crash course in confidence and fierceness -- but does too good a job.

June struggles to make ends meet and comes up with a creative way to make some extra cash for this month's rent. She decides to mass produce and sell her homemade jam, but when Chloe gets in on the action, she takes it to a whole new level. Meanwhile, James launches his own line of super skinny jeans called none other than 'Beek Jeans,' of course.

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 likeability on "Dancing with the Stars".

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.

It is crunch time and James goes into serious training to be in top form for "Dancing with the Stars." Luther is tasked with the duty of keeping James on a strict regimen, but leave it to a jealous Chloe to try and sabotage it. Still, that's the least of their worries when embarrassing photos of James leak all over the internet.

June has been so stressed and consumed with work that she has no time for anything else, including Chloe. Chloe's remedy for this is to slip June an herbal relaxant, but the next thing June knows, it's Tuesday and Monday is a complete blackout. As she tries to piece together what happened, June discovers some surprising things about herself. Meanwhile, James grapples with the idea that he may have impregnated June's friend, Crissy, on her wedding day.

June is startled when a man she has never seen before jumps out of a door in the apartment that she has never seen before. It is Teddy, Chloe’s childhood friend from Camp C.U.T.S. (Callous Unemotional Trait Survivors) who visits her every year when he goes off his medications. His visit coincides with the Carter Marsh Annual Warehouse Sale, where Chloe uses psycho and manic Teddy to her advantage against all the vicious out of town women at the sale. Meanwhile, James is devastated when he finds out that his Beek Jeans have been relegated to the “cooling rack” at the sale where no one is buying them.

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. Meanwhile, James is struggling to land an audition for a new Woody Allen film “Monte Carlo, Monte Carla.”

James invites Chloe and June out to dinner to meet the girl he has been dating, Emily. At the dinner, Chloe after barely talking to Emily says “Veto”, forcing James to break up with her. Meanwhile, Chloe has begun working at a cell phone store, where she can fight with customers all day, and James has become fat, soft, and complacent.

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.

Chloe tells June that Benjamin is going to be in town to shoot a commercial with James. She is excited and has even moved him up to #1 in her guy rotation. June tells Chloe that she has to tell him about her rotation if she really likes him.

Chloe hires a private investigator to track down the original bitch in Apt. 23, Trish, whom Chloe has been seeking revenge on for years.