High school sweethearts Maddie and Nate cross paths again when Nate comes back to their hometown to give a lecture at the local hospital. Although Maddie is still hurt from their past breakup and tries to keep her distance, they eventually develop a friendship. Nate supports Maddie in securing funds to expand her cupcake business. Just as their romance reignites, Nate discovers a job opportunity in Boston. Heartbroken, Maddie returns the promise ring he once gave her and focuses on the grand reopening of her shop. Nate soon realizes the significance of what he left behind and faces a choice between pursuing his career in Boston or staying in his hometown with Maddie.