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They were originally the main romantic couple of the show, alongside Liv and Holden, before Josh and Maddie started dating. They are portrayed by Dove Cameron and Ryan Mc Cartan, who were engaged in real life (see: Dove and Ryan (relationship)). Like, I know you came down here to spend the whole summer with me, but I just...
However, Choose-A-Rooney was filmed before they got engaged. Both, Maddie and Diggie are the captain's of the Porcupines basketball teams. I really feel like this is something I have to go do! Diggie: Maddie, wherever you are is where I want to be.
Diggie and Maddie are close friends and are dating.
After almost breaking up because of a misunderstanding, they shared their first kiss at midnight in New Year's Eve-A-Rooney, during a web cam chat. Both originally wanted to gift each other with the same thing (sweat bands).
Due to Liv's actions, Maddie sends Diggie a sweat band while Liv hides his present and instead gives her a porcupine.
To make it up to her sister, she has Diggie fly in. (Maddie blushes) Maddie: Hey, I hope you don't mind that painting of my boyfriend...
This marks their first face-to-face reunion after a couple of months. Maddie: 'Cause, like, I know that it's kind of goofy, but no matter how far apart we are, I look up at it, and I think, like, y'know, we're gonna be okay.