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Gee.
If I was single and I was having a night out with a single women that I was interested in (now or in the past) then I'd be hoping for it to lead to something. But I'd not assume it either.
He'll be watching for signs and wondering what the expectations are. You should be able to send some signals I'd think, without saying it.
And don't be offended if he makes a polite pass. After all, it has been known to work.
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