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Dean/Ruby - also known as Duby to shippers - is the het pairing of characters Dean Winchester and Ruby in a romantic or sexual relationship in fanfiction.

Duby was at its most popular in Season 3, before Ruby entered a canonical relationship with Dean's brother Sam in Season 4. (See Sam/Ruby.) Duby shipping was fueled by the end scene of 3.09 Malleus Maleficarum, which showed Ruby seemingly opening up to Dean. That said, it was a fairly unpopular pairing even then, due to Ruby's own general unpopularity.

You may also be interested in Sam/Bela, Dean/Bela, or Sam/Ruby.