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.

James goes against Chloe's advice, succumbing to June's urging and attempting the unimaginable - dare we dream? -- a Dawson's Creek reunion! Along the way, he makes some shocking discoveries, veers slightly off course and encounters some stars of television past.

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 obsessed with PEOPLE magazine's annual Sexiest Man Alive issue, though Chloe tells her she shouldn't be such a sheep by letting others tell her what's hot and sexy. To prove her point, and in true Chloe fashion, she swoops into the PEOPLE magazine offices in an attempt to put James on the cover this year. James is thrilled by the prospect, and now June suddenly finds him irresistibly attractive.

Chloe and June have different feelings about Thanksgiving - Chloe hates it, June loves it. Sadly, June can't afford to fly home this year, so Chloe persuades June to come with her to her parents' house for the holiday -- but under the most strange and awkward conditions. Meanwhile, James volunteers at an exclusive celebrity soup kitchen in order to get a photo opp, and is unpleasantly surprised when he and Luther get roped into actually working.

Chloe teaches June to "network," i.e., to go drinking in the financial district, but when Chloe lands herself a hot young broker whose father is a Wall Street mogul, she also lands June a dream job offer! But there are strings attached, and June must make a tough decision. Meanwhile, James' worst nightmare is realized when he's paired with the worst pro-dancer.

The premiere day of "Dancing with the Stars" has finally arrived and James is in LA in prime dancing form, while Chloe is back home taking some liberties with James' empty penthouse with one of her infamous scams. June tries to step in and teach Chloe the importance of honesty... that is, until her own belief system is shaken. And when James finally step into the spotlight, mouths will drop.

Everyone is in a bit of a funk -- June is obsessively awaiting news on a potential job and James is down on his luck -- so Chloe drags everyone along on a weekend getaway to the Hamptons. It's Chloe's mission to have the ultimate rager, crash the party of the year and hook up with the illusive host. However the road to debauchery keeps taking the wrong turn down paths of reflection.

June is nervous and excited about starting at Harken Financial. Things go surprisingly well, and she even meets an incredibly nice co-worker, Fox Paris. Chloe warns June, though, that she shouldn't be so trusting and that Fox is probably just keeping her enemies close. Meanwhile, Mark looks to James for help in expressing his newfound feelings for June.

June and Chloe attend their first tenants' meeting after a new family moves in the building, but they make a scandalous scene and June quickly realizes that she needs to clean up Chloe's act so that they're not branded the floozies of the building. However things backfire when Chloe decides to set her sights on Mark, which is then further complicated by James' attempt to sabotage June's virtuous efforts.

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 and Mark are obsessed with a reality dating show, and Chloe convinces June to go out there and actually get in the game herself. But when Chloe and June end up asking the same guy out, they get sucked into their very own pseudo dating show, with James orchestrating various dating challenges as they compete to win this guy's affection.

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.