Madison Witt is an interior designer who has thrown herself into work, and focused on climbing the ladder. That is until her best friend's boyfriend, close friend of Madison's. Aiden Marshall calls out of the blue and says that he wants to propose to her best friend, Jessica Thorton. Which causes Maddy to have to fly to Connecticut for the engagement and wedding. On the other side of things, Aidens best friend, and coworker, Nathan Hartley has to fly in from Boston for the engagement as well. When Aiden springs the idea and responsibility to plan and run the wedding and parties surrounding it, Maddy and Nathan, who do not generally like each other, have to spend a year planning and attending parties surrounding their best friends. Will the two learn to like each other and get along? Or will their differences drive a wedge in between friends and family and ruin this wedding?