Sarah (Diane Lane), is 40 and recently divorced. Believing Sarah needs to date more, her sister, Carol (Elizabeth Perkins), creates an online dating profile for her. Simultaneously, Jake (John Cusack) reluctantly decides to try Internet dating. Sarah and Jake meet, and though both agree they are not interested in a serious relationship, their chemistry is undeniable. But, when Bob (Dermot Mulroney) suddenly shows interest in Sarah, her future with Charlie becomes unclear.