Teenage Herman Raucher (Gary Grimes), summering on Nantucket Island with his sex-obsessed pals Oscy (Jerry Houser) and Benji (Oliver Conant) during World War II, meets Dorothy (Jennifer O'Neill), a newlywed in her 20s whose husband is off at war. As his friends awkwardly attempt to woo girls their own age, Herman slowly befriends the older woman and finds himself becoming increasingly in love with her, until a sudden tragedy changes their lives forever.