Normally, Jessie reads Zuri a bedtime story, but this time Zuri reads the story, which soon places all of them into a medieval world. Tony will do anything to please one of the princesses, which is Jessie, but there is another guy fighting for her, who is supposed to represent a guy named Brody in the real world. In the real world, a guy named Brody asks Jessie out on a date, which actually causes Tony to become jealous, just like in the medieval story. Both of the boys go on a great medieval "adventure" in the story to try to get Jessie to be their princess. They joust for Jessie, but Tony is obviously weaker than Brody. Besides the medieval storyline, Tony is conflicted about Jessie and Brody going on a date together. In the real world, Jessie finds out Brody also has another girlfriend and decides not to go on a date with him. Tony asks Jessie out on a date and she accepts.