Meet Savi, a successful career woman working toward the next phase in her life—both professional and personal—simultaneously bucking for partner at her law firm while she and her husband, Harry, try to start a family of their own. Savi's free-spirited and capricious baby sister, Josselyn, couldn't be more different—living single, serial dating and partying, and regularly leaning on her big sister along the way. Their common best friend, April, a recent widow and mother of two, is rebuilding her life after tragedy and learning to move forward, with the support and guidance of her closest girlfriends. And friend Karen, a successful therapist with her own practice, reconnects with the girls after her involvement in a complicated relationship with a patient goes far too deep.

A young guy short on luck, enrolls in a class to build confidence to help win over the girl of his dreams, which becomes complicated when his teacher has the same agenda.