Amanda's fiancé ends their relationship after Amanda's mother had already sent out the wedding invitations, and Amanda, a Yale graduate art teacher living in Boston, spirals into depression. Her fiancé had told her she was too sad and suffocating. Amanda brings the wedding dress she had picked out to her art classroom and lets her first graders paint all over it. The principal tells her that her actions are inappropriate and unprofessional. At the end of the school year, Amanda is let go from her job as a teacher. Over the summer, Amanda begins babysitting one of her former first graders named Nathaniel. The two go on little excursions every day, getting ice cream or donuts, going on walks, and visiting attractions. The two become close as they spend time together. Amanda can tell that Nathaniel's father wants to sleep with her from the way he stares at her. Amanda's parents ask her when she is going to paint again, and her friends tell her she needs to get back on the dating scene. Instead, Amanda gets drunk with a man her friend set her up with and shows up hungover to work the next day. One day, Amanda and Nathaniel visit a shop that sells Russian dolls. Amanda, intrigued by the form, buys unpainted ones online and begins painting them: first, one of her and Nathaniel, then, one of Nathaniel's dad, then, her fiancé, then, one of everyone she knows and sees. She paints the figures as a progression of life, with the smallest doll being a baby and the biggest an old person. She takes pictures of the figures and imagines putting on art shows. At Nathaniel's seventh birthday party, Nathaniel and his father ask Amanda to come on their family vacation with them. She tells them she cannot come because she is moving back to New York, where she is from. Nathaniel begins sobbing, and when Amanda gives him a map she made of the places they visited together, he rips it up. His parents cannot console him. Amanda takes him into her arms, telling him she is sorry, and she understands.