The Marriage of Bette and Boo takes place in 1950s suburbia. Still unmarried in his early 30s, Boo is wallowing in his alcoholic father’s shadow, when he meets Bette, who in her 20s is still worrying about her high school popularity. Insecure and yearning, Bette seeks redemption and fulfillment in motherhood, though her ideal children are based on a sentimental Hollywood movie and characters in Winnie the Pooh.