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It can represent a shared secret and that simple gesture can bond two people in a mischievous way by allowing them to communicate without words. Winking can also be used to convey approval, but the most widely sought after wink is the provocative wink that may affirm a more intimate connection.
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It depends. He could be trying to pick you up or telling a joke.
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It means he is probably my parents age.
He might have something in his eye
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