June can't afford to fly home for Thanksgiving, so Chloe persuades her to come to her parents' house, but June begins to feel uncomfortable and awkward due to her past encounter with Chloe's dad and when Chloe gets June to pretend to be wheelchair bound. Meanwhile, James volunteers at a celebrity soup kitchen in order to get publicity and is unpleasantly surprised when he and Luther actually work.
Chloe teaches June to "network", but when Chloe lands herself a hot young broker whose father is a Wall Street mogul, she also lands June a dream job offer. However, when Chloe's beer goggles affect her perception of his appearance, June tries to keep Chloe drunk to keep her job. Meanwhile, James turns to June's mom for advice as his worst nightmare comes true when he is paired with the worst pro-dancer for Dancing with the Stars.
Chloe takes a dejected James and an anxious June on a trip to the Hamptons, along with Robin and Luther, and tries crash the party of the year and hook up with the elusive host. However all does not go to plan.
June is nervous and excited about starting her new job. 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 to get his wing-woman back.
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.
Chloe hires a private investigator to track down the original bitch in Apt 23, Trish, who Chloe has been seeking revenge on since she stole her dream of becoming a dancer on a popular dance show years ago.