Dexter Charming is sensitive, caring and shy. With his kind and modest attitude, the girls of Ever After High enjoy his company, Cupid in particular. Dexter also feels slightly overshadowed by his brother Daring. He follows the Royals.
Cupid has a huge crush on Dexter, and she admires his eyes. Although she knows of Dexter's crush on Raven (as revealed in "True Hearts Day Part 1" when she helps solve his flustered attempts.) Cupid knew of Dexter's crush on Raven for a while, however noticed that he was somewhat shy when revealing his crush to others. Despite that, Dexter enjoys Cupid's company and the two hang out a lot.
- ―Cupid drifting.
Daring and Dexter are two unlikely friends, however the two are brothers and they get along often. Dexter secretly feels overshadowed by Daring's bold personality and figure, by charming the hearts of girls, especially his crush, Raven Queen.
- “If I was the great Daring Charming, girls would just fall for me. Literally.”
- ―Dexter about Daring.
Raven believes that she and Dexter are just friends. Dexter was the first Royal to ever want to talk to Raven, so Raven believes that Dexter is more than just a copy of his brother. In the books, Raven shows that she might enjoy Dexter and his company, as Dexter enjoys Raven's. She stays true to herself, as he believes and isn't afraid to take risks. Dexter has been constantly trying to ask Raven out to dances, however Raven ended up doing that, as seen in "Catching Raven".
- “You know, Briar's having that party on Friday, and I wanna ask Raven to be my date, but I'm-I'm just afraid I'm gonna mess up.”
- ―Dexter about Raven.
As Apple is the leader of the Royals, Dexter follows to be a Royal however isn't confident in some places. Apple believes that Dexter requires some work if he wants to be like his brother, and sees him as a second-rate person. Even so, Dexter knows of his brother overshadowing him.
Lizzie has been disrupting Dexter's flirting with Raven with her typical Queen of Hearts attitude. Throughout "True Hearts Day", she has been ruining his chances with Raven, albeit unintentionally.