I'd like to offer up my Ishmael to plot with Calufray?
Ishmael is conniving, deliberate, and rather self-centered. He looks at other Soquili as playthings and abuses them until he is bored. He often targets pretty mares and harps on their insecurities to break them, and it's that raw emotion of being broken that Ishmael gets the most enjoyment from (besides making his brother Belial crazy - that's number one). Ishmael however also enjoys flirting and trying to make mares fall for him before breaking their hearts. Hearts and feelings are fair game, and nothing seems to amuse him more.
Since Calufray is kind of self-conscious she'd be a toy for him, but she is also astoundingly pretty, so Ishmael may instead try to win her heart. And... if things go in the right direction (especially since I adore Calufray!) his heart may open up to her as well?
Lemme know what you think! (: