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In The Great Gatsby, thus pens Fitzgerald:

‘However—I want to see you.’
‘I want to see you too.’
‘Suppose I don’t go to Southampton, and come into town this afternoon?’
‘No—I don’t think this afternoon.’
‘Very well.’
‘It’s impossible this afternoon. Various ...‘

We talked like that for a while and then abruptly we weren’t talking any longer. I don’t know which of us hung up with a sharp click but I know I didn’t care. I couldn’t have talked to her across a tea-table that day if I never talked to her again in this world.

It's a conversation between the narrator, Nick, and his quasi-partner, Jordan, followed by Nick's commentary.

I'm struggling to interpret the conditional sentence. Does it mean,

I couldn't have talked to her that afternoon, even if it meant I would never see her again.

Or,

Even if this had been my last chance to talk to her, I couldn't have done it.

Or something else?

More elaboration on the possible dialect or register that would featur such a structure is appreciated.

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    That’s a very unusual sentence indeed. It took about five read-throughs of the passage until I finally arrived at a way of reading it that made sense. That interpretation matches the first of yours: he’s saying that he couldn’t have faced talking to her across a tea-table that day, not even if refusing to see her meant that he never saw her again. – Janus Bahs Jacquet Nov 20 '18 at 17:32
  • What @Janus said. It might have been less "unusual, awkward" back in Fitzgerald's day, but it certainly stands out a bit today. On the other hand, no-one would bat an eyelid at I couldn’t have talked to her across a tea-table that day [even] if it killed me. Maybe that's just because [even] if it killed [you/me/him] has become something of a "set phrase". – FumbleFingers Nov 20 '18 at 17:42
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Let's reorder this and take out some descriptors:

If I never talked to her again, I couldn’t have talked to her that day.

"if" here, meaning that we're making a supposition that the rest of the statement depends on:

Supposing/On the pretense that I never talked to her again, I couldn't have talked to her that day.

Which to me seems like this falls into what you expected--it's saying "Even if this had been my last chance to talk to her, I couldn't have done it."

I think what makes this so strange is that the "if" isn't a concessive clause (an "Even if"), so we get no feeling of "despite the fact" even though it seems to be implied. This lack of emphasis on the comparative "if" is what--in my opinion--makes this whole thing hard to parse. If I were to rewrite the sentence, it would look like:

I couldn’t have talked to her across a tea-table that day--even if I never talked to her again in this world.

Using both the dash and concessive clause to emphasize the conditional and make sure it's understood correctly.

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    I agree with this answer. For extra clarity, the paraphrase could add "—even if I were never to talk to her again" or "—even if I knew I would never talk to her again". This would clarify the temporal relations: the "never talking to her again" would have taken place after the tea-table talk (not before or during). In addition, I would say the construction used is colloquial. – Cerberus Nov 20 '18 at 18:44

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