Hannah and Libby need a miracle. The PR agency they inherited from their grandmother is losing clients left and right, and the sisters are devastated at the thought of closing. The situation seems hopeless--until in walks Lou, an eccentric self-help guru who is looking for a new PR agency. Her business could solve all their problems--but there's a catch. Whoever works with Lou must complete a twelve-week challenge as part of her "Crush Your Comfort Zone" program.

Hannah, whose worst nightmare is making small talk with strangers, is challenged to go on twelve first dates. Libby, who once claimed to have period cramps for four weeks straight to get out of gym class, is challenged to compete in an obstacle course race. The challenges begin with Hannah helping Libby train and Libby managing the dating app on her sister's behalf. They're both making good progress--until Hannah's first love rolls into town, and Libby accidentally falls for a guy she's supposed to be setting up with her sister.

Things get even more complicated when secrets come to light, making the sisters question the one relationship they've always counted on: each other. With their company's future on the line, they can't afford to fail. But in trying to make a comeback to honor their grandmother, are they pushing themselves down the wrong path?