C.A. Cupid's heart may be for Dexter Charming, but she happily offers guidance when he needs help asking out Raven Queen to Briar's party. Can this shy prince find the courage to charm her?
Briar's hosting a party and Dexter wants to ask Raven to go with him. However, he lacks the courage to approach her and instead stares dreamily at her from behind his locker's door. C.A. Cupid shows up behind him, hoping for a nice chat with her crush, but she quickly realizes that's not going to happen. Dexter tells her of his problem, explaining he'd like to be more like his confident brother. Cupid suggests him to try his "asking out"-skills on his friends, hoping Dexter will try with her. However, Dexter is so enthusiastic about the idea that he immediately runs off to try his skills on his other friends.
During Science and Sorcery, Dexter tries asking Briar, but she just falls asleep, per her destiny. His next plan is to test his luck with Maddie during a walk, but he blunders through his sentence so badly, that Maddie just thinks he speaks Riddlish, a Wonderlandian language, too. Finally, he tries to woo a troll girl, which works, but ends with him covered in kiss-obtained slobber.
Defeated, Dexter returns to Ever After High for some solitary sunset watching on the balcony. Unexpectedly, he is joined by Raven, who often comes up to watch the sunset. Even more unexpectedly, she asks him to Briar's party, explaining that going with a friend puts less pressure on her. Dexter eagerly accepts and makes a victory dance when Raven leaves that has him falling from the balcony into the bushes below. Cupid just so happens to be sitting there reading, and Dexter makes use of the opportunity to thank her for advice. He gives her a kiss on her cheek, leaving her giggling happily.