Ooooo this is spicy, and omg thank ya ❤


•He’d be interested in the taboo sense of their relationship, a sleeping with the enemy type of thing. So I do think it’s something very plausible. He kind of likes the challenge and it would entertain him

•Definitely not telling anyone in the Troupe. He’s not the type who’s open with those sort of things anyway. It’s not so much that he’s concerned about their judgement, since he is the boss and he knows no one would severely oppose him and ostracize him, maybe just voice their opinion. It’s really just that he doesn’t think it’s their business as long as it doesn’t interfere with the Troupe

•And that’s something that would be quite difficult. His s/o being a Hunter means she could easily be after the Troupe, and even if he really liked her (obviously would have to enough to be in a relationship with her) he’d have to put the Troupe first. So there could be lots of tension there

•If they ever actually encountered each other under the pretense of it being like ‘Troupe vs good guys’, like a fight, then it would be even more difficult. I don’t think Chrollo would mention anything to the Troupe even then, but he’d maneuver around the situation in his own way, getting a message to his s/o to warn her, but in a sly way, like “If you’re smart you won’t get caught up in this”