Hmm...I don't know. It depends on when she meets David. He's a bit of an ass in his teen - early 20's years. Bit like his Uncle Dean with his partyin' ways without a real sense of responsibility. Mary might get annoyed with him.
Hmm...maybe I used the wrong word. David's irresponsible in the sense that he doesn't have anyone to look out for. He's free to come and go as he pleases, pretty much. (Jack has made it quite clear over the years he doesn't need his brother hovering, and David's okay with that.) He doesn't have any real problem hanging over his head - like Dean, John and Sam's search for the Yellow Eyed Demon.
He hunts because it's fun and it's the family business. Until, reality knocks him on the head and he realizes 'party time is over.'
But crunching numbers on a desk just wasn’t as fun as hunting.
So, I'm thinking Mary might be hanging out with the wrong Winchester from your 'verse. ;D
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Okay, correction: it's a good thing Mary isn't hanging out with David because she'd probably use him as Wendigo bait on a joint-hunt.
She can handle his ass-y personality (she's not exactly Miss Sunshine), it's the irresponsibility that'd do her in.
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He hunts because it's fun and it's the family business. Until, reality knocks him on the head and he realizes 'party time is over.'
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