In this era of digital communication, 16-year-old Madeleine and her four eclectic friends are negotiating the emotional turbulence of teenage life in the Berkshires of Western Massachusetts by creating and posting YouTube video diaries. The diaries are a microscopic look into the contemporary landscape of adolescence; sexual confusion, dubious antics, and existential angst. Mad is the center of her single mother, Iris' struggle to parent and produce a living, as a visual artist. This pursuit often includes Mad and her friends' participation in the creation of Iris' edgy paintings. Iris is the eccentric, breezy mom every kid wants. Mad's reality is shattered when she discovers that Iris has a serious illness. Forced into adulthood, Mad grapples with these harsh circumstances as her friends rally around her. They accompany Mad on her journey, inspired by the links she uncovers to her mother's surprising past.

Over the summer of 1942 on Nantucket Island, three friends -- Hermie, Oscy and Benjie -- are more concerned with getting laid than anything else. Hermie falls in love with the married Dorothy, whose husband is an army pilot recently sent to the battlefront of World War II.