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.

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.

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 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.

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.

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.

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.