Illumi Zoldyck

•Honestly, Illumi will already understand the concept of being gentle, it’s not really a new concept or something he needs to learn per se. If anything, he just needs to learn to take his s/o’s concerns to mind rather than brushing them off as meager precautions

•He’d apologize for hurting her, but would think it was silly and a little dumb that he needed to watch himself, all for the sake of being “gentle”. It’s even more disconcerting when they try to teach him through cuddling and all that fluffy stuff. It’s honestly not likely to work on Illumi

•He’ll be quite awkward, would maybe try to keep it in mind and understand the appeal, but it’s just not going to be an easy progression for him. Illumi’s been raised to ignore fragility, and that the only right way to live is to remain resilient, so it’s only to quell his s/o’s concerns that he’ll actually give it some thought

•At the most, he’d take those considerations into mind and might try holding her hand on his own one day, but that would also be quite awkward. He’s not smooth and subtle, he asks them “Like this?” Or “Is this how I’m supposed to do it?” His grip will be much too tight though, and he just like, snatches her hand randomly, it’s so weird

•It might come off as sarcastic (though that’s not really Illumi’s style) or dull, as usual. Sincerity doesn’t come easily for Illumi. Or if he is sincere, his emotions don’t exactly relay it in full. So if he happened to hurt her again, maybe he went to hug her and squeezed too hard, or pinched her cheek out of some weird display of affection, he’d say something like “Oh! I forgot! I wasn’t being gentle just now.”