Alison Greggory, portrayed by Olivia Holt, is a beautiful young lady, who's parents have messed up the meaning of love for her. She gets sent away to boarding school while they deal with Gus Greggory, the new accidental baby. When Alison finds out that Quinn Lyson, Gus's mother, is the Grand Academy headmistress she's thrilled. Quinn, on the other hand, expected that Alison would be furious. With the help of Quinn, and Alison's three new friends, Vincent, Nelson, and Jess, she learns the true meaning of love. That is, after she becomes known as the school's boy steamer. When ever a boy is tired of their girlfriend, they make out with Alison. Alison thinks its just another affair in her life, but really love isn't supposed to consist of affairs. Quinn, Vincent, Nelson, and Jess struggle to teach her. When Alison finally realizes she must do something about her parents' marriage before another baby is given a crappy life because of them. But...Alison doesn't know what to do, and gives up. Vincent has to step in just in time. Gus's life is saved, and Alison gets a baby to watch over.