Gerade als Tony seinen ganzen Mut zusammen genommen hat, um Jessie um ein Date zu fragen, kommt ihm ein gut aussehender Junge namens Brody in die Quere und fragt Jessie zuerst aus. Zuri ist besorgt, dass Jessie mit dem Falschen ausgeht und hilft deswegen auf ihrer Art ein wenig nach …
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.
Jessie croise par hasard dans le hall de son immeuble Brody, un beau jeune homme, qui vient rendre visite à sa grand mère. Elle tombe immédiatement sous son charme et, poussée par Emma et Luke, accepte l'invitation à dîner que Brody lui propose... Tony en devient jaloux.
ג'סי פוגשת בכניסה לבניין בחור נאה שגם מרשים את ילדי המשפחה, וכשהוא מזמין אותה לדייט היא נעתרת בשמחה. אבל זורי דווקא בעד טוני השוער, וכדי לסייע לו היא מספרת לג'סי סיפור אגדה עם מוסר השכל.
Jessie y Zuri leen un cuento que los transporta a todos hacia una época medieval.
Jessie incontra un affascinante ragazzo di nome Brody che tenta di conquistarla con fare galante e chiedendole di uscire. Zuri, sospettando di Brody, racconta una storia a Jessie, ambientata in un contesto medievale, nella quale i personaggi immaginri rispecchiano quelli reali. Sir Tony farà di tutto per conquistare la principessa Jessie, così va dal mago Merlino per avere un suggerimento su come conquistarla.