This is like a poker question. And just as poker questions need context (actions on all streets, stack sizes, history with opponent, etc.) this also depends on circumstances.
Almost certainly, yes.
But it would depend. Would I do it for the Afghan war vet who plays with us once in a blue moon and works in the service industry? Probably not.
Even for the guys with the country club memberships, though, I am going to think twice about this when it happens the third or fourth week in a row.
You can still be a good host, though, and you can still treat people like adults.
"Hey, man, maybe it's just not your night?"
"Hey, let's just grab a drink outside a second."
Ultimately if pressed I'll probably go ahead with the transaction.
But I have control over the invite list, and they might not get a follow up invitation.