Okay, so demon cherubs are one of those concepts that sounds like a random webnovel generator spit it out, but once you see it in practice, it kinda works? I read this one serial where the male lead was this terrifyingly powerful demon lord, but he had these tiny, bat-winged cherub imps that followed him around. They weren't matchmakers in a cute way; they were more like... chaotic neutral relationship accelerants. They'd steal the heroine's hairpin to give to their master, or eavesdrop on her conversations and report back with hilariously wrong interpretations.
It completely flipped the usual dynamic. Instead of a slow-burn will-they-won't-they with brooding stares, you had these little gremlins actively creating situations of forced proximity and manufactured drama. The romance became this awkward, funny, and surprisingly tender thing because the demon himself was too prideful to admit his feelings, but his own minions were blatantly shipping it. It made the power imbalance way more interesting—he commands legions, but he can't control these pint-sized troublemakers who are obsessed with getting him a girlfriend.