I'm often wrong with my predictions - But I feel like there's a strong possibility for this event to end with some kind of Mutual-Masturbation.
It's not an act that appears very often in these kind of games, so bear with my reasoning folks.
If Dylan will get "at least as far as Sam" then a climax for Sophia seems as good a scoring line to measure progress as any.
Also, as this scene continues the narrative from Sophia+Dylan Part 1 I could see the event ending with Sophia getting riled up but not wanting to do something that she'd regret. So she excuses herself to the bathroom (or somewhere else) to Jill-off, realizes the door is ajar but decides to not stop - then she remembers Dylan's confession about watching her. She could be imagining Dylan watching her without knowing that he is actually watching her.
If the event culminates in Dylan's room and the evening more or less ends there, I personally would be a bit disappointed.
I'll play a little with the ideas I've already described and that have been uploaded here by other members.
Sophia and Dylan take a cab to the restaurant. During the ride, Sophia notices the cab driver's glances that keep resting on her and then glide to Dylan. Perhaps the driver also smiles a little insinuatingly. If Dylan has done everything right so far, then Sophia (the player) has the choice of snuggling up to Dylan somewhat provocatively. Then when they get out of the cab, it's more as a couple than as mother and son (second teaser).
In the restaurant, Sophia is challenged by Dylan (after "two" glasses of wine) when she tells him that she has already sat in a similar restaurant without panties. He does not believe her. Sophia, whose inhibitions are lowered by the alcohol, goes to the ladies' room and then puts her panties on Dylan's seat.
When the two leave the restaurant, they decide to walk home (I don't want to discuss whether this is possible). Their way leads them through the park through which they were jogging. When they pass the bench where the homeless people were sitting, Dylan sits down on the bench and they both remember the event. Sophia is drunk and a bit horny. Maybe she thinks about how those men looked at her and replays the scenes in her mind. Maybe she says something like "Maybe I should have shown them THAT!" and strips off the straps of her dress.
At the end of the scenes she kneels on the bench in front of Dylan, Dylan sucks on her breasts while Sophia, fingers deep in her pussy, pleasures herself.
Once home, Sophia remembers her panties. Before disappearing into her bedroom she says to Dylan, "You still have my panties, you can keep them until tomorrow." (That would be a really kinky ending to the evening for me).