Lady Calpurnia Hartwell, one of society's invisible wallflowers, tosses her lace spinster cap into the fire and begins searching for excitement and adventure. She starts a list of experiences she desperately wants to try. Kiss someone passionately, smoke a cheroot, gamble at a men's club, the possibilities are endless. Before Callie loses her courage, she arrives at a notorious rake's doorstep to ask for her first passionate kiss. Callie has secretly loved this man for years and yearns for one embrace to start her on her new quest.

Gabriel St. John, the Marquess of Ralston, embraces his role in society as an unrepentant rogue. After watching his father fall into permanent despair after his wife runs off, Gabriel swears never to love. His lifestyle comes to an abrupt halt with the surprise appearance of his Italian half-sister. He knows the hardships she will endure as their mother's illegitimate daughter. When Lady Calpurnia arrives seeking a favor, Gabriel snares her in a trade. If she will help his sister in society, Gabriel will assist her in her adventures.

As Callie draws Gabriel into her wild escapades, he fights his attraction to her. He romances beautiful and sophisticated women, not plump and plain ones. Gabriel cannot understand why Callie intrigues him so much.

Debut author Sarah MacLean pens an entertaining tale of two mismatched lovers who find happiness despite their many differences. She tempts readers with her cast of fascinating secondary characters that beg for books of their own.