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Oh bleh, moderating OKCupid is the worst. I made an account to see how the site worked, then left it alone for six months. Then I was invited to be a moderator! Then I spent a few hours deleting pictures of genitals and... well, just like you said, arguing with other moderators about whether or not some creepy message from a creepy guy was creepy enough to be too creepy. I gotta say, though, they have some well-put-together moderation tools. I've been a volunteer moderator for several other sites and none have had such a streamlined moderation UX as OKCupid. It's really a power multiplier for moderators and a great example of how important UX can be to get the job done.