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While both are horrendous, I think we can say that having intimate photos of you taken without your knowledge being spread is worth than having photos you took being spread. The reason being that in the first case your rights to privacy were actually violated twice.

No.

Thanks for the interesting discussion. Anyway after further thought I came to agree with you because the person in the second situation also had their privacy violated twice when they had the video/images stolen from their device and when it was spread without their consent.

But I think it's pretty self-evident that doing multiple wrong things to do one final wrong thing is worse than just doing the final wrong thing.

He's pedantically pointing out a superficial difference between the two cases, and pretending as though he therefore demonstrated some profound ethical or moral difference between the two. Good job on calling him out on this and pinning him down!

I agree that they are both horrendous!