Two years ago, Jenna made Robby question his life in Chicago and why his job kept him there. Now Jenna's small town brings Robby home. Since their summer together, however, everything has changed. Jenna is recovering from a bad relationship and dealing with the associated trauma. She plans to become a journalist and leave Wheaton behind, so spending time with Robby is a terrible idea. Robby always wanted to work in the finance industry, but he didn't go to college to make rich people richer. He hopes to gain a new perspective when he visits his grandparents, but he keeps running into Jenna, who he left on rocky terms. Robby's sister and the rest of the small town keep forcing them together, and they can't deny their attraction. However, a shared affection isn't always enough to guarantee a happy ending.