Are they any books that you've read a million times because every time you feel just plain sad you open them?
For example, mine are I'd Tell You I Love You But Then I'd Have to Kill You by Ally Carter, Harry Potter, or any of the Tortall books by Tamora Pierce.
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Have you read Gaiman's short Forbidden Brides of the Faceless Slaves in the Nameless House of Dread Desire? That's a good one (though perhaps a bit strange to be a comfort story, haha)
my comfort book is The Hitchhiker's Guide to the Galaxy by Douglas Adams, its funny, so it cheers me up