I don't know that I would think a lot about it. I know a bunch of people, including my Grandpa and my uncles and a few of my cousins, that wink all the time at people when they are talking. To them the wink doesn't necessarily mean anything, it's just a signifier that they acknowledge you standing there. Sometimes it embarrasses me when they do it because some people take it the wrong way.
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Well that's pretty broad. I wink at friends and co workers especially when I'm joking around or I'm trying to get them to pick up what I'm laying down. What was being said as he said it?
I don't think there is anything conclusive here.
He could be flirting, it could be friendly, he could just be goofing around.
A wink can be any of those things.
You need to look for other signs.
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It's because he thinks you're sexy.
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