Dove is the most sought after wedding planner in Chicago, known for creating perfect fairytale weddings. When she is hired to plan a lavish society wedding, she accidentally sends an intimate, detailed email about her growing attraction to the groom himself instead of her assistant. Mortified, she expects to be fired. Instead, the groom confesses he's having doubts about marrying his controlling fiancee. He proposes a deal, for her to help him figure out if he's making a mistake, and he won't tell anyone about the email. But the more time they spend together, the more Dove realizes she wasn't wrong about her feelings, and neither was he.