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Am I an idiot? I can't unlock Cassie's route, I've tried talk down, feeding her,  then forcing past the toll guy then sleeping, I have tried talking her down, forcing past the toll guy, then sleeping, to no avail. What am I doing wrong?

did you return to slums?

You need to have access to Cassie's safe house, then do the slums toll thing, and you need to accept a certain job from the Don.