Celebrity actor James Van Der Beek's bitchy friend Chloe rents a room in her New York building to naive, ambitious country girl June Colburn. As usual, Chloe expects to cheat and pester the tenant to leave without her deposit. To James's amusement and winning Chloe's respect, June puts up a surprisingly good fight. Reward and revenge come rolled into one, in all senses naked proof that June's fiancé Steven is a serial cheater.
Studly biker Scott is too attractive for June to turn down the blind date Chloe pushes her to, which even leads to great sex. Her reluctance to go on when she finds out Scott is Chloe's estranged father graduates to indignant shock when her mother arrives, in a wheelchair, desperate to patch up her broken marriage. Nosy neighbor Eli analyzes the psychological minefield.
James Van Der Beek accepted a part without reading the script just so he could work with child star Kiernan Shipka, but it's a body swap and learning to be a pre-teen girl in his studly body proves extremely hard. he does however learn to appreciate fan adoration again. Chloe makes most of her yearly income during the annual half week UN general assembly opening. Yet she finds that too exhausting and wants an assistant like James's. To avoiding paying one, she takes a foster daughter, Molly, and tricks unsuspecting June to sign up as Lesbian co-guardian. Naively ...
Even Chloe is impressed by model pupil June's progress after lessons in New York-assertive attitude, even feels somewhat threatened when she gets into the limelight with James. However the cocky act shrivels when June is invited to her former fiancé Steven's wedding. James agrees to play along after Chloe gets them in at the arm of Hercules-star, whom she made believe it's a benefit for his mother's disease, MS.
James cheerfully profits from his popularity by launching his own, butt-flattering jeans line, even though it's hell on his literally crushed manhood. His manager Luther refuses further credit as long as Chloe hasn't read his script, and rent is due. Just when June despairs, praise for her home made jam inspires selling a batch of it. Chloe helps her, but actually sells Eli secret camera footage for a fetish website, without factoring in that only pays off after 50 days and his day job is food inspector. June finds out, but Chloe sees no reason to apologetic, on the ...
James is initially shocked when he learns a sex tape of him and Chloe is being released on video. After consulting media experts, he only worries about the unflattering amateur production and plans to discretely remake it professionally, but Chloe develops a most atypical 'conscientious' objection. An assertiveness push from Chloe gets June to seek distraction from her ex's wedding in a one night stand. Charles, the heavenly hot coffee-shop customer she fancies, turns out to share enough interests to agree, but even less resilient emotionally when it's time to break ...
James stresses over the prestigious largest dressing room when casted alongside Dean Cain, so his assistant Luther's job may be on the line. June is barred from Chloe's nightlife circle because she can't drink on doctor's orders. Brooding at home, she discovers Chloe cares enormously for a cartoon based on her and hopes this provides on angle to get back in the loop.
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.