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You have to unlock the Ken/Samantha sharing route. Then RNG when Ken and Samantha are fucking talk about how Ken has never learned to swim. Then go to the pool and pay money to rent the pool the whole day.

how do i unlock the ken/samantha sharing route? is it the choice with ken after taking a photo with Anna or something else?

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?

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.