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.
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 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 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.
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.
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.
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.
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.
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.
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.
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.
