TV producer Jun Hyeok (Ahn Jae Wook) has harbored a secret crush on Chae Young (Kim Hye Soo), the sister of his middle school friend Yoon Cheol, since they were teenagers. He's determined to confess his feelings someday, but to Chae Young, Jun Hyeok is merely her brother's friend. Chae Young dreams of a destined love and is now past thirty, still unmarried. As her last remaining friend gets married, she grows anxious and begins going on blind dates. One day, after meeting up with her married friends, a dejected Chae Young drinks herself into a stupor. Seeing her state, Jun Hyeok, impatient, seizes the opportunity to confess his love under the influence of alcohol, only to be met with a cold rejection. Jun Hyeok loses all hope and falls into despair. At this point, a senior colleague, a makeup artist, proposes a brilliant plan: disguise himself as a woman to approach Chae Young. Thus begins Ahn Jae Wook's grand cross-dressing operation...