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It means either he is joking, playing a trick on someone else and wants you to go along with it, little Jimmy is stuck in the well again, or he likes you.

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Sometimes people will just be friendly, and this is what some men will do. In my opinion when a man winks at you it's either he like you, or maybe he is trying to tell you something especially if this man is your friend. Try not to be concern about this.

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Q: What does it mean if a guy winks at you?
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