Chris is 24. He comes from a wealthy middle-class background and is a self-made millionaire. He admits that in the past he has relied on his wealth and material objects to succeed in the dating world, but now he wants to find love with a woman who loves him for who he is and not what he has. Undercover Lover follows this millionaire bachelor disguised as an average cash-strapped guy, as he goes on a series of dates to find a woman who will fall in love with him rather than his wallet.