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Men: Does a wink towards a woman always mean flirting?

Anonymous
Hey all, I have a question for you. Not sure what to make of this or do about it, if anything.

I hear that earlier generations use winks for a plethora of reasons, such as parting, joking around, indicating an inside joke or secret, etc. Especially so for men, since their winks are less apt to be taken seriously.

Thanks to the dawn of social media, my generation sees winks almost exclusively as flirting.

That said, my boss (50m) has recently started winking at me (25f) all the time. Not when telling a joke, or talking about somebody. Mid conversation, he'll look to see if anyone is looking, and wink at me with whichever eye isn't in the other people's field of vision. The context of the conversation is always innocent, too, so the wink doesn't even make sense. Yet, he still manages to wink. Not to mention, he'll sometimes even do it twice, a few seconds apart. Not so much a "wink wink" as a "Did you see the first wink? Here's another, just in case." Almost always followed by a big smile.

Do you guys think he's being friendly or trying to go somewhere with the winks?
I've seen him wink one time at a male coworker before, which makes me wonder.

A little bit of background story: He is in a long term relationship and I'm married to someone my age. He has flirted with me subtly in other ways as well.
Men: Does a wink towards a woman always mean flirting?
Men: Does a wink towards a woman always mean flirting?
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