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Dexter is shy and tentative. He is friendly, but unlike his brother, he is not very suave or charismatic. This becomes even more pronounced when he talks to Raven Queen, whom he has a crush on, one on one. At times, he has a tendency to compare himself with his older brother, Daring. Ironically, Dexter is jealous of his brother's ability to impress any girl, unaware that he himself possesses an enchanted gaze that makes girls swoon. The effect is broken when his gaze is not immediate, like when he wears his glasses.
Dexter has light skin, brown hair with a cowlick and deep blue eyes. He wears a small gold crown and glasses. He is the only Charming ever to wear glasses.
Having a knack for technology, Dexter is often asked to help his fellow students when their MirrorPad or other gadget stops working. That being said, he works with Humphrey Dumpty as one of Blondie Lockes's camera crew for her MirrorCast show, Just Right. Dexter mostly enjoys gaming on his computer, which he spends most of his time doing. He also takes a fancy to building robots and is part of the tech club. Despite being a technology-driven individual, he also likes reading traditional books.
He is the son of King Charming and Queen Charming and brother of Daring and Darling. According to The Storybook of Legends, he is nine months younger than Daring, while The Unfairest of Them All notes that he is the older twin brother of Darling. While he and Daring can have a good time in each other's company, their relation is burdened by their father favoring Daring. Dexter gets along better with Darling, not just because she is his twin, but because they both have doubts about the destinies laid out for them and only trust each other to share these doubts with. According to the Ever After High books, Dexter has numerous cousins and each set uses the same first letter in their names. The cousins are Bountiful, Breathtaking, and Beloved, Charity, Courageous, Cherished, and Caring, Elegant and Errant, Fragile, Fearless and Fairest, and Good-Enough, Gallant, Glorious, Gutsy, Gracious, and Gorgeous. His grandparents are Alluring and Auspicious Charming.
Dexter often hangs out with the other Royals, in particular his brother and Blondie Lockes. He and Humphrey Dumpty appear to be closely acquainted, as Dexter also worked with him to run the voting site for Thronecoming. He does not have particular interaction with any Rebels except for Hunter Huntsman, who is his roommate and also has fallen in love outside of his story. He is also friends with Raven Queen, who he has a crush on and usually talks to her for supportive advice, and C.A. Cupid, who's always there to help him and vice versa.
Dexter's pet is a jackalope who goes by the name Mr. Cottonhorn.
C.A. Cupid has a crush on Dexter, but he is unaware of that. He sees her as a precious friend. Dexter has a crush on Raven Queen, but has had trouble expressing himself, in part because he isn't supposed to like her that much due to the Royal/Rebel conflict swirling around. She had become aware of his crush on her ever since "True Hearts Day", which she responded positively to. In the webisode "Chosen with Care", Dexter asked Raven out on a date to the movies, which she said yes to. In "Way Too Wonderland", it seemed as if he and Raven have gotten closer since their date at the movies. He seemed to have been worried about Raven when she had disappeared off to Wonderland, hugging her in relief when he saw her again.