Trevor aims his Cupid love arrow toward Jack, a radio disc jockey with a love for classic rock n' roll, and one of his listeners, a single mom named Sarah. On the couple's first date, Jack and Trevor arrange a performance by Robert Harrison, the lead singer from the indie band Future Clouds and Radar. All is going well until Jack unintentionally disappoints Sarah's 13-year-old son, Adam; and Sarah discovers a secret about Jack. Also, Claire becomes smitten with a handsome statistician who is helping her create a test that matches people up based on their commonality - a concept she readily embraces.