Fics like Should've Just Asked

Despite their age gap and differing social circles, Castiel has struck up a warm friendship with Mary Winchester, a wealthy widowed socialite. When Castiel needs a place to stay, Mary invites him into her house, where there’s loads of spare room. Castiel’s aware that they make an odd pair, but he doesn’t fully realize how things look to outsiders, especially to Mary’s eldest son. All Dean Winchester sees is that his mom has apparently hooked up with a hot young guy (who is totally Dean’s type) and that makes things… weird.

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