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ITA I think that was the moment when he realized she was much more than just a chick who liked playing bad-girl. She moved him because he recognized someone who was struggling as well, imo.
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Yeah and I think that Dylan felt like an outcast from his friends (before the intervention in S5) and that Val was the only one who can sympathize his pain. That's probably why he didn't care that she was a bad influence on him.