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Yeah he's not bringing it up for some reason. I'm already Day 85+ and it's still the same dialogue. So I accepted his offer, took the photo, didn't start the sharing route with him (I think it's Anna so I didn't accept), accepted his offer to buy groceries,  and completed Samantha's hacker, beach, and sex scenes. Am I missing something here?

The trigger for Ken's dialogue about being a virgin is when you invite Ken on Thursday to the entrance, select (Sharing Route) option after the photo.