Hi
Lust&Passion, first of all I want to clarify that my criticism tries to benefit your game, so I try to be the most objective possibly and not obey just to my personal taste.
The problem is that the reward that Dylan wantend (her mother wearing sexier clothes) is too little, too bland, for all the plan he made with someone, as you say, he doesn't even like. As I said Dylan can see Sophia in underwear and bikini in his own house, so wanting see her with sexier dresses in school for his own pleasure doesn't seem to justify all that he planned. Also, in the game was never mentioned before something like Dylan had worries about a Sophia's midlife crisis and it's not like she dresses like a nun or something, she wears pretty fine always. For example, the outfit with leggings that she had when she swings Dylan is pretty sexy, modern and youthful. So, from all the directions the plan seems absurd.
On the other hand, I think you should think not only in the reasons that Dylan could have to make that plan, but in the consequences of incorporating a twist like that in the story too. Dylan's character has been generating a lot of sympathy and empathy in the players as a shy and bullied boy. Many people was roothing for Dylan because of that and they had a huge expectation about what would happen after the self defense training, that was a suspenful part of the story. But now everything collapses: Dylan now is immensely dumb, a manipulator, he tells Aiden what to do, is not shy anymore, and Aiden was not bullying him. Then, this likeable character loses his charm. All in just one scene.
My advise is just simply delete those dialogs about the Dylan's confession. Cut it out. The expectation of what will happen between the bullied and the bully will still there. That conflict situation will continue being interesting and Dylan will not lose fans unnecessarily. I will give you an example: Back to the Future. Do you think that movie would have the same reputation without the Marty's conflict with the bully Biff?