Uriel did say in 410 that Castiel had a weakness : he LIKED Dean. Since there was no Angel story between 407 and 410 (end of 409), I guess it means that by the end of 407, he already liked Dean (maybe since 401!)... So Cas may be grumpy and all but he still likes Dean by the time your story starts. He just doesn't express it really well cause he's an angel and he's awkward. That's my theory and I'm sticking to it (until proven otherwise) cause it makes me happy.
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Uriel did say in 410 that Castiel had a weakness : he LIKED Dean. Since there was no Angel story between 407 and 410 (end of 409), I guess it means that by the end of 407, he already liked Dean (maybe since 401!)... So Cas may be grumpy and all but he still likes Dean by the time your story starts. He just doesn't express it really well cause he's an angel and he's awkward. That's my theory and I'm sticking to it (until proven otherwise) cause it makes me happy.