Penny Beck is a girl who says yes when she means no. She keeps to herself, follows the rules, and does what she's told. After a disastrous experience with her boyfriend, she's determined to change from the spineless person she's always been into the strong woman she wants to become. All she needs is a little practice. On a cross-country trip to check on her grandpa, she strives to become bolder and more outspoken with the strangers she meets. Penny's plan is to practice saying and doing what she wants without worrying about what anyone else thinks. Then she meets Archer, an introspective loner to whom she finds herself drawn. She realizes she does care what he thinks, very much. Will Penny be able to stick to her plan, or will she revert back to her people-pleasing ways?