The Cosmopolitan staff learn there is no environment more competitive than the magazine industry in NYC; the team prepares for a high-profile cover shoot with Ruby Rose; Diandra Barnwell runs into romantic complications.

After Joanna Coles announces shocking news, the Cosmopolitan staff fear for their future; executive beauty director Leah questions her place at the magazine; senior fashion editor Tiffany clashes with her coworkers.

Joanna Coles finally hands over control of the magazine to Michele Promaulayko; the fate of the core staff is in jeopardy; an epic clash over a guest list for an exclusive party causes a divide.

At a star-studded Milan Fashion Week, Tiffany comes face to face with an international controversy. Back in New York, Diandra struggles to pull off Cosmopolitan's biggest live event of the year while James and Steven escape the city for a secluded getaway that turns romantic.

The Cosmo staff get an offer they can't refuse when the new Editor in Chief, Michele Promaulayko, gives them a lavish house in the Hamptons for a weekend getaway. As the coworkers get to know each other more intimately, Tiffany's budding relationship with Evan attracts attention, forcing Diandra to admit her true feelings and confront the situation head on.

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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.