Joanna Coles prepares to make a huge announcement to her staff. The search for a new fitness contributor is complicated by Diandra's romantic feelings for one of the candidates. The staff prepares to shoot Ruby Rose for an upcoming cover.
Tiffany clashes with coworkers during New York Fashion Week. Diandra and new fitness contributor, Evan, flirt. Leah struggles with changes at the magazine.
The staff gets to know new Editor-in-Chief, Michele. Steven and Diandra clash over the invite list to Philip Plein's party. Evan learns the hard way that Diandra doesn't want to mix her personal and professional life.
Diandra puts her issues with Steven aside to focus on the "Fun Fearless Money" conference. Tiffany and James attend a controversial fashion show at Milan Fashion Week. Steven and James get closer than ever before on a trip to the Poconos.
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.
The staff's plans for shoots in the Bahamas grow complicated when hurricane threatens to hit. Diandra and Evan get stuck in Miami on a scout. Steven gets a surprising suggestion when asked to find a model to join Evan on his shoot.
Adam struggles to impress Leah and Michele during the "Tips and Sips" shoot. Diandra worries she's becoming the object of office gossip. Tiffany's love life gets complicated.
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.