Even though his sons tease him about not dating anyone and his ex-wife thinks he's still obsessed with her, retired school principal and sculptor William Everett Larson, 53, is glad he he waited until he found 47-year-old high school art teacher Jessica Daniels. He admires Jessica for her bold writing and the way she manages her life. However, Will believes that the only part of Jessica damaged by the past is her heart. Jessica assures Will that she is unable to love for long, but Will refuses to believe that this is true. Yes, this is a problem because Jessica's past experiences cause her to view dating as fun and men as interchangeable. But when she offers him temporary sexual fidelity, Will decides to take what he can get until he finds a way to convince Jessica that she is still capable of love. Jessica Daniels is overall happy with her life. Her daughter graduated from college. She has a few years left until retirement. Life is good, although lately she has ceased to be interested in both her art and men. Since Jessica has never been the type of woman who is looking for that one special man to start a family with, she usually dates and enjoys all the men she wants. What's wrong if she's happy with it? Will is definitely cute and charming, but she's not sure he's worth the trouble that comes with dating just one person. She likes riding his motorcycle, really likes his art, and thinks he's basically a great guy. But after thirty years of living alone, Jessica knows that most relationships simply don't work out for a woman with her past. When Will continues to insist on sleeping with her, she finally gives in. But deep down in her heart, Jessica knows it won't last long.