When Mallory discovers that her boyfriend, Jeremy, is cheating on her with an online girlfriend, she swears off boys. She also swears off modern technology. Inspired by a list of goals her grandmother made in 1962, Mallory decides to "go vintage" and return to a simpler time (when boyfriends couldn't cheat on you online). She sets out to complete grandma's list: run for pep club secretary, host a dinner party, sew a homecoming dress, find a steady, do something dangerous. But the list is trickier than it looks. And obviously finding a steady is out ... no matter how good Oliver (Jeremy's cousin) smells. But with the help of her sister, she'll get it done. Somehow.