Editor-in-Chief, Joanna Coles, makes an announcement that shocks the staff of Cosmopolitan Magazine as they are preparing to shoot Ruby Rose for the cover of the magazine. The staff is asked to help hire a new fitness contributor for the magazine, but things get complicated when Brandon Coordinator, Diandra Barnwell, finds herself attracted to one of the candidates, Evan Betts.

The staff has to deal with the fallout of Joanna Coles's shocking announcement. Senior Fashion Editor, Tiffany Reid, rubs some of the other staff the wrong way during New York Fashion Week. Executive Beauty Director, Leah Wyar, worries about her place at the magazine.

Cosmopolitan's new Editor-in-Chief, Michele Promaulayko, gets acquainted with the staff. Bookings Director, Steven Brown, clashes with Brand Coordinator, Diandra Barnwell, over the guest list to a party thrown by fashion designer Phillip Plein. Joanna Coles gets emotional over leaving the magazine.

Diandra continues to clash with Steven while helping to plan Cosmopolitan's annual Fun Fearless Conference. Tiffany attends a controversial fashion show by Phillip Plein while in Milan for Fashion Week. Steven and James take a girls trip to the Poconos and get closer than ever before.

A trip to the Hamptons leads to some surprising situations for the staff. Tiffany's growing closeness with Evan shocks her coworkers. Diandra confronts her feelings for Evan.

In the midst of preparing for a large scale beauty and fitness shoot in the Bahamas, the staff gets word of an approaching hurricane that threatens to ruin all their plans. Meanwhile, Diandra and Evan's relationship heats up when they are are sent to Miami to scout alternate locations, and Steven gets an unexpected suggestion about who should model in the magazine's fitness shoot.

Diandra and Evan's secret romance reaches new heights, but with Cosmo gossip at an all time high, will Diandra damage her professional reputation? Adam pushes himself to the brink of a nervous breakdown trying to impress Michele, and Tiffany's dating life takes an unexpected turn.

Joanna's plans for more changes at the magazine puts everyone on edge. Leah gets unexpected news. Diandra and Evan's relationship hits the breaking point. Tiffany stains a borrowed skirt.