After doing some thinking, I think the Dylan event will be quite predictable.
What we know:
- Dylan has to catch up with Sam. Or at least get close.
- Dylan and Sophia will talk about virginity.
- The progression of the game is speeding up.
What will happen (IMO):
Dylan and Sophia will talk about her losing her virginity. Dylan will talk about the fact he still has his, and he feels bad about it. Using the normal logic of this game, Sophia feels bad for him. Dylan jumps on the chance and talks about the time he stole a kiss from her (at the soccer match) and that Sophia was mad about it. Sophia, of course, feels bad for him. Dylan will then ask to kiss her as "practice". Sophia feels conflicted, on one hand, he is her son. But on the other, she already made out with Ellie, Jules and Sam. So she agrees to kiss him.
Then Dylan starts grabbing on her. Predictably, Sophia thinks it's cute and gets hot and bothered. She'll probably be talked into showing herself to him too. After all, it's just "sex ed". Which I believe has been discussed as a theory before.