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I think he always knew, actually. He just didn't count on it being necessary to find out what that "much more" entailed. Dylan tried to nip that possibility in the bud early on when he told her he didn't want anything to do with her if she lived at the Walsh house. "You're Valerie?"
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I hadn't seen it that way and it totally makes sense
Especially when Dylan is just the kind of person who can see through people's bs and shields right away (except when too much emotional baggage is involved...aka, anything that has to do with his parents), so it's no surprise he sensed the deal with Valerie right away but at the same time he didn't have the emotional strenght to care enough.
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Apart from moving him, Dylan was also in a unique position of vulnerability with her early on. This woman who's supposed to be emotionally disposable is the only one who knows the secret he's carrying, that he lost all his money in a scheme and for some reason needs to pretend, for his friends, that it didn't happen. She already knows that he fears being disowned by those who supposedly don't matter anymore.
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ITA
Gosh, this makes me remember how much I felt for Dylan in the scene where Val discovers that he's the one who took money from the After Dark's income. Dylan was incredible vulnerable at that point and his friends had no idea about what was going on
