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I'm having some difficulty starting the date with Rylan. Going to his room while he's inside only gives me the interactions from before the update, and going to his room while he's gone leaves me at the locked door.

I'm having the same issue :(

(+1)

Maybe you need more friendship/desire points with him, check the guide --> https://lust-odyssey.fandom.com/wiki/Rylan

My current save file has 20 friendship points and 15 lust points with Rylan, which is enough according to the guide. I've also landed on Sithyrya. What are the exact requirements that need to be met for the date event to occur?

I don't know where you are reading that, but the total points are 20 (friendship and desire). There is also a requirement to have landed in Sithyrya for the first time. That's all.