In January 1946 a British military transport plane departs from Shanghai on its to Tokyo, Japan. During the flight the airplane makes an emergency landing on Sado Island. The residents on the island have heard stereotypes of the British soldiers and have mixed feelings about the their new "guest." Nevertheless, for the next 40 days the islanders take care of the crew members until the plane can take off once again. This includes Chiyoko Morimoto who is the daughter of the inn owner where some of the British crew members stay.

Holly, a professor at a small college, has had a long history of finding the wrong guy. She’s accomplished quite a bit in her life, but after her younger sister announces she is pregnant, Holly decides she is going to make an effort to meet Mr. Right. Meanwhile, David, another professor, is a single father, very smart and kind, but not the type that Holly takes notice of when the two are assigned to plan the Christmas Formal. At the insistence of her best friend, Holly signs up for the dating website “Cupid’s Arrow,” where she meets Josh, an attorney just hired by the school. He’s everything she wants on the surface, but has little to say beyond his work and good looks. Josh and David were roommates in college, so Josh recruits David to write poetic messages in an attempt to win Holly over.

London Bridges, a fast rising Hollywood starlet, with her pampered pomeranian Latte in tow, arrives on location for "There Will Be Oil" to see that she won't be receiving the star treatment she is used to.