Ken will eventually say he's a virgin, you can either offer Anna or Samantha. I don't know if it's required but I told him earlier that Anna's my mom. Anyways, choose Samantha, and you show her 3, Beach/home/blowjob, pics of Samantha and try to convince both to try it out.
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?