Selina is a couples therapist and unofficial dating coach who knows exactly how to help people find love, but her expertise is put to the test when she goes on a date with young billionaire CEO Hugo Norton while impersonating her best friend, who was matched with him through a prestigious matchmaking company. The disastrous date should have been the end of it, but Hugo’s grandmother Ruth, a close friend and long-time sponsor of Selina’s, has other plans. Determined to help her emotionally distant grandson find love, Ruth forces Selina into a thirty-day arrangement as Hugo’s live-in dating coach. As Selina attempts to teach the stubborn and impossible-to-match Hugo how to have a successful relationship, their constant clashes gradually give way to an undeniable attraction. But with Hugo’s complicated childhood, Ruth’s regrets, and Selina’s own growing feelings getting in the way, the woman whose job is to help others find love may discover that she has fallen for the one man she was never supposed to date.