Daring Charming is very self-obsessed and loves looking at himself in his mirror. He is a Royal. His father, King Charming, encouraged him to follow his destiny due to his looks and positive attitude. Daring is also very charming towards girls and his smile can make any girl swoon. With this, Daring is very full of himself and is very flirty towards girls.
Daring and Apple just consider themselves friends, however the students of the school believe otherwise, as they believe that Daring and Apple should start dating right away, after the Enchanted Forest dance when Daring asked Apple out, making Duchess Swan burn in jealousy, and she soon started spreading lies around the school that Apple slipped love potion in Daring's drink, which they thought was rather silly. Nevertheless, Apple admires Daring's contributions and commitment towards his story, however believes that Daring is the main Charming and main figure. Also, in Date Night Apple and Daring go to the movies together, though they are not dating, as Apple is still happy to marry Daring later on in life.
- “Blondie, Daring and I are still not a couple. This is high school! We have forever after to be together!”
- ―Apple to Blondie.
Dexter often feels overshadowed by his arrogant brother, Daring. Other Royals also believe that Dexter is a version of Daring with dark hair and glasses, which causes him to have insecurities about his unknown destiny. This could also cause a problem when flirting with girls (i.e. writing love poems to them, as he done so with Raven Queen in "True Hearts Day Part 1") as Raven mistook him for Daring, with his bold figure instead of Dexter's.
- “'Sup, brother?”
- ―Daring to Dexter.
Duchess shows a great affection for Daring in the books, and it is likely that it would be revealed in one of the upcoming webisodes. Duchess shows great jealousy towards Apple as she gets Daring Charming to herself, throwing in a Happily Ever After and a good student and grade reputation. Duchess, meanwhile, has no friends, however she will do anything to try to get Daring's attention. Duchess once threatened Ashlynn Ella in order to be paired up with Daring, Ashlynn's partner. They haven't appeared together in the webisodes yet, but it is revealed in Kitty's Diary that Duchess and Daring had been dating.
In Lizzie Hearts Fairytale First Date, Daring attempted to woo Lizzie for a bet from Sparrow and Hopper. After a few failures, the prince managed to impress her with a dragonback ride. However, Lizzie wished to keep up her reputation as an aloof future Queen of Hearts, oblivious that Daring was dared in the first place. He also attempts to woo Lizzie in A Wonderlandiful World and Next Top Villain. Also, spring unsprung may suggest his crush on Her, as they ride on the fairest wheel together. Daring also looks proud of lizzie for her effort on the spring fairest dresses.
- “I’ve never been on a date before.”
- ―Lizzie to daring.
As seen in Raven's Tale: The Story of a Rebel, Daring and Cerise hang out with the same people and have had a passing relationship, but it appears to be nothing more than a "Hey". In The Cat Who Cried Wolf they ran against each other and in Thronecoming he made it clear at first that he thought Cerise was nothing more than a damsel that needed saving. He soon changed his mind when the bookball team was not doing too well and called on Cerise to help, for which she obliged. At the Thronecoming dance, having taken back what he thought and said, that she was a damsel-in-distress, Daring asks Cerise for a dance and again she obliges him, but they are not dating. Though in Cerise's profile it states she is drawn to ''the leader of the pack", possibly stating she has a crush on him.
- “Wait a spell! I know a damsel who might just be able to rescue us!”
- ―Daring about Cerise at the Bookball Championship.
In Ashlynn's Fashion Frolic, Daring was laughing at the evil stepsisters in the audience, when they tripped in the food.
As the BFFA of Apple, Briar too is a popular Royal. Briar and Daring have lightly interacted, the first time being when Daring caught her when she was happily plummeting in "Apple's Tale: The Story of a Royal", and soon dumped her on the ground. As Briar extremely enjoyed the moment, she proposed in repeating her action, with Daring waiting to catch her.
- “Catching damsels-in-distress, it's kind of my thing.”
- ―Daring to Briar.
In Kitty's Dairy, Kitty poofed in front of Daring after hearing him ask Duchess out on a date and questioned him. Daring seemed surprised that Kitty had heard.
- “"What about your date with Duchess?" "Excuse me?" Daring asked.”
- ―Daring's reaction to Kitty's question.
As revealed in the books, Daring underestimated Raven's abilities, as shown in "The Storybook of Legends". Since Raven ripped out her page, people were less afraid of her now, including Daring. Therefore, Raven thought it was safe to assume that Daring wrote her a love poem in "True Hearts Day Part 1", however misunderstood as Dexter was the one who wrote it.
- “I never wrote you a poem.”
- ―Daring to Raven.