I understand the perspective of desperation but you have to understand, he IS her son and she is not into incest or anything immoral with her own son, to begin with, so he HAD to start pushing harder to bring down those restrictions and reservations in his case compared to others that might have had it easier because are not related to Sophia in a way that yes, it may have looked pushy or desperate in the beginning.
When he saw her in her red lingerie in the living room and that she did it for his father and after the talk with Amber's son in his room, he wanted to have the same experience and relationship with her as his father does or even better than him like the foot massage or the bikini fashion show. Now that those reservations are lower, he doesn't have to be that pushy or desperate because there's already a trust, love and a sort of intimacy between them.
As for learning what his mother likes to wear lingerie wise?...maybe eventually he'll give her lingerie as a gift or have a lingerie fashion show, he already knows what she likes. Haha yeah, that's one of the things I like about Dylan's path, the cleverness because, for the bikini fashion show, he learned her size when getting her bikini before going to the bathtub and give her the foot massage, then Sophia told him about the one-time thing about her naked breast and he bought the white crochet bikini, now that she told him about the lingerie...he might use that knowledge to give her something.
The thing with the game and what I like about it in Dylan's path is that is a very realistic approach of Mother & Son Incest. Dylan is after all (don't know how to put it) peddling? rowing? against the current, because Sophia is his mother, and he has more adversity than compared to others, so he needs to be extra smart and at the same time sweet, kind, useful, helpful, to get to where he wants to get with Sophia in a way that can be acceptable for her and even willing.
I've never seen another game that takes this much time to develop a Mother & Son relationship in as much as realistic as possible.
