In 1949, Charlotte's dream of a career in advertising is shattered when her father demands she help out with the family business. Meanwhile, Charlotte is swept into the glamorous world of the Miss Subways beauty contest, which promises opportunities with its Park Avenue luster and local fame status. But when her new friend-the gorgeous fellow-participant Rose-does something unforgivable, Charlotte must make a decision that will change the lives of those around her forever. Nearly 70 years later, advertising executive Olivia is pitching the NYC subways account in a last ditch effort to save her job at an advertising agency. When the boss she's secretly in love with pits her against her misogynistic nemesis, Olivia's urgent search for the winning strategy leads her to the historic Miss Subways campaign. As the pitch date closes in on her, Olivia finds herself dealing with a broken heart, an unlikely new love interest, and an unexpected personal connection to Miss Subways that could save her job-and her future.