it’s a no-win. the classic rock-and-a-hard-place. a lose-lose. a pickle. a crunch. a conundrum. a double-bind. a dilemma.
yup. there is no truly right response here for that man.
i have learned to preface things i talk about – for instance, “i just want to tell you this. i want to go on and on. i want to _________ (choose: rant/think/ponder/ruminate) aloud. please do not try to solve this. please just listen.”
but sometimes, yes, indeedy, sometimes i just talk. with no preface. and then, in the way of conversation, especially in the middle of the night pillow-talking, he talks after i talk. and – whammo! – that’s where he makes his mistake.
reverse threading 
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