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Jim Ralston could always bring a friend home to dine without notice. The Ralston and Lovell wines rounded off the effect, and even Joe's drawn face had mellowed by the time the Lovell Madeira started westward.

My understanding so far is that "the Madeira started westward" means "the bottle was almost empty." Is that the meaning of "the Madeira started westward"?

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It means the madeira is running out. The phrase "go west" means to die or disappear, or figuratively to run out. It's an analogy, almost certainly, to the sun setting in the west.

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