Illumi Zoldyck

•He doesn’t really think the whole concept of flirting through enough to understand the best approach, so it’ll mostly be impromptu. He can’t really apply his assassin training to flirting, only the aspect of “manipulating” people? Illumi takes it a little too seriously, so his persistence can come off the wrong way if he takes it that far. But he can also gauge the situation, understanding when his efforts weren’t getting him anywhere, so he could back off and strategize another way to approach the person of interest

•He’s very forward and brash. He thinks flirting is simply flattery to try and persuade someone’s emotions, so he’d pick out little features or quirks about the person and make comments. ‘Comments’ because it’s not really like a compliment. It’s just so blunt, almost sounds offhand, like “I see that your hair has no split ends” and “Your face shape is exceptionally round”

•It’s slightly unnerving, simply because he’s so expressionless and it contradicts the whole concept of flirting. He tilts his head a lot, lets out awkward little laughs, and attempts these fidgety little smiles that just make it look so forced omg he’s so dorky. There’s no saucy mannerisms that he can offer to go along with his flirting that would ease the process, it’s just too out of character. He’d be lucky to pull off a demure smile at the most

•He does make lots of eye contact, so if that’s something that the person finds appealing then sure, that might work. Those big, dead eyes might be scary though

•The only suave flirting he can really accomplish is if he’s paying close attention to what exactly they want to hear, and what pulls the most rewarding reaction from them. If they seem to like attention on their physical features, he’ll go with that. If they prefer tribute on their personality and demeanor, he’ll try for that. It’s still not very smooth, still indifferent, but at least he’s putting in effort