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In my reply I pointed out the Aiden rout was the weakest. The points you made just bear that out further. You got a bully, Aiden, with a gang... he gives tasks to Sophia that do nothing for him. Instead of making a play for Sophia himself. The entire rout is flawed.
First you can send Dylan to boarding school; or Sophia can go through these tasks. Not to mention Dylan gets some special training and ends up beating up a drunk in the park.
Ok--So a kid on a power trip doesn't want to have sex with Sophia and just makes her do stupid things. I imagine the boarding school would hinder any Dylan/Ellie development in the story but doesn't seem to be the case. Somehow in a few training sessions Dylan can kick ass... it took me a little longer than a few days to become proficient in hand-to-hand combat.
See what I mean why this story arch is flawed?
It's hard to have a compelling blackmail route. In any type of game. I haven't seen a realistic one. Most of the ones in porn movies are also unrealistic. You have to have some sort of suspension of disbelief to make it work. With that in mind, I would say that Aiden's path is on the better side of blackmail stuff.
It is clear that his end game is fucking Sofia, maybe even sharing her with his gang, like he did with Jennifer and Andre. But jumping straight to that kind of request would easily be denied. This is why I find the Bennet route the weakest. His blackmail is so thin, there's no way Sofia would fuck him.
Coming back to Aiden's route. Even his 4th tasks would have been refused by Sofia if it was his first request. And things are escalating. This would be similar in mentality with the sunken cost fallacy. The more you invest in something, the less you are likely to give it up. What you invest can be anything, time, money, whatever, the psychology behind it is the same.
I mean if she had the options, fuck Aiden or send Dylan to school, she would definitely not have chosen the first one. But dress sexier doesn't sound like that much. And the "cost" of keeping Dylan safe is increasing bit by bit. That's why he keeps giving her his tasks as late as possible. First part of the task, second part. To be just one more small step to complete it. The more she invests in this route, to keep Dylan safe, the harder it is to say no to the next small step.
Now I don't know if L&P thought of all that when he implemented it into the game, it is also kind of unrealistic for a kid like Aiden to be able to think of this strategy on his own and on the fly. But if you can get over that part, I think his path is not so crazy compared to the most of other ones (like Ellie, Dylan, Sam, teaching sex ed to the kids..., Bennet).
What do you think?