I have a few different variations on Jackson’s biology, dependent on interaction and such, but regardless of biology, his parents are still the Whittemores. His relationship with them has always been strange, even before he found out that he was adopted, but especially after. He struggles with identity because of the adoption — how does he relate to two people who aren’t really his parents? But he’s also struggled because he’s always been afraid to delve into finding out more about his “real” parents, the Millers. What if they were horrible people? Even worse — what if they were amazing people? What would they have wanted for their son, someone they’d never even met either? Would they be proud of him?
The questions haunted most of his teenage years, his developmental years, and that’s what turned him into the asshole that he became in high school. His parents overall were kind people though. David and Lily Whittemore are hardly bad people. In fact, as far as parents go, they’re incredible compared to a lot of the others around town. They work a lot, true, but they couldn’t have had more love for their son and truly wanted to be parents. It’s only when Jackson starts to distance himself that they allow him that space.
Another parent might get invasive, ask too many questions, or “require” love out of a son who had decided to detach himself from them as parents — but they stuck with him and gave him space to grow. Unfortunately, Jackson didn’t return the kindness, but they continued to be patient with them. They spoiled him, but I don’t think he was without reprimanding either. He was no stranger to getting into trouble — when they noticed him doing something wrong. Well-intentioned as they were, his parents were also rather oblivious, but not because of wanting to be.
Most importantly, in canon, when Jackson was going through everything, they weren’t oblivious to that. David immediately goes to the Sheriff to report something wrong because Jackson’s text was unusual. He goes off of a simple text to know that something is wrong with his son. They still give their son space, they don’t pry when he breaks down in his room, and though they probably make recommendations, they don’t know how to really and truly help other than thinking he’ll come to them when he’s ready. Their fault is in being too generous in this respect.
When all is said and done and Jackson begs them to let him leave, he comes clean about a lot — or at least what he can. He tells them he’s going through something and that he needs a break from the town. Going to London starts out as a temporary fix, a vacation. And when he requests to stay, they give in and allow it. He may not know how to love his parents in a traditional sense, but Jackson does love them — and I think he learns how to say it by the end of high school. To let them know that he does in fact appreciate what he’s been given his whole life: Freedom to choose.
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