When Henry asks his secretary, Mildred, to marry him, he's rather taken aback by her immediate refusal. In his mind, he's taken her on several dates, and at nearly forty years old himself, it is the natural course of their relationship to get married. Whereas for twenty-nine-year-old Mildred, she's been looking for romance, to feel wanted, loved, and be swept off her feet - something she's never had from stuffy Henry! With his ego bruised, can Mildred challenge him to 'up his game' across every aspect of his life?