Dean and Cas know that they can't have each other but Dean knows thats not going to stop him. Cas doesn't want to get in trouble but even more he doesn't want Dean to get in trouble. This is after all, Dean's last straw before he actually goes to jail.
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What happens when Dean has a one night stand with a girl he doesn't even know? Doesn't even know her name.
Will Cas expect Dean having a little girl?
Will Cas get jealous?
How will Sam react to Dean not hunting?