Jacob and Briana both come to their relationship with baggage from previous relationships. Jacob was hurt in his relationship with Amy when she refused to make allowances for his anxiety disorder and appeared to purposely ignore his needs to maintain her own social life. This hurt was compounded when Amy fell in love with and became engaged to his brother, Jeremiah. Briana was married for 10 years to a man who was in love with another woman during the majority of that time. The end of her marriage then brought up memories of being abandoned by her father as a young child and having to help her mother raise her younger brother.

Briana finds it impossible to trust Jacob based on her past experiences, and she pushes him away. Several times in the novel, Jacob turns to his mother for advice on Briana, and she consistently tells him that love shows up, meaning that when people love each other, they are there for each other, no matter what. Jacob takes this advice and shows up for Briana at Grant House, and it leads to the trip to Grant House where Briana admits her love for him for the first time.