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I think in certain echelons of society, that means "What did you do this summer?" I've had customers at work ask each other that and often the answer is "Well, we're spending three weeks at our home up north, taking a trip to visit our daughter at college, and we'll be around here planning the gala after that." I don't think it's that abnormal, I just tend to ask "What are your summer plans?" or "What did you do this summer?" so it's not as off-putting.
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