Sarah Bloom is an up-and-coming New York City wedding planner, she the owner/operator of Love's in Bloom Events. While she plans weddings, she is so focused on her career that she doesn't have time for a wedding of her own, let alone date. She has the biggest professional opportunity and challenge to date when she gets the job to plan the wedding for Abby and Tom. The opportunities include the fact that Abby comes from a high-profile wealthy family which will only increase Sarah's own professional profile if she can pull the event off, and that it has attracted the attention of Wedding Insider magazine as a possible cover article, the magazine which would not even consider her company for an article on Sarah's previous first-time submission. The challenges include the wedding needing to be in two weeks' time to accommodate Tom's military schedule, the many demands that Abby's mother Barbara places on Sarah to meet her own sensibilities, and that Abby and Tom want to hold the wedding on the farm of Tom's small town Williamstown, Massachusetts family, far outside of Sarah's cosmopolitan views of the perfect wedding.
An overriding factor on both the opportunities and complications is the fact that Tom's brother is David Nichols, Sarah's teenage sweetheart, who now operates the farm where the wedding events will be held. While Sarah knows the town and the farm, she will have to deal with David in the wedding planning, they who have not seen each since she left town. Although Sarah and David did not split on bad terms - it being more a matter of their different lives, with David happy on the farm, and Sarah yearning for a big city life - it has still been years of unresolved feelings with which they will have to deal. On top of everything, it is harvest season on David's working farm, which may kibosh many of the plans Sarah has for the event. While the feelings each has for the other do bubble close to the surface, their different lives may still be an obstacle to pursuing a relationship a second time around. In addition, Payton Ellis, the representative from Wedding Insider, has his own designs on Sarah, the two of them matched more closely at least on paper.