He may just be clowning around and it may just be his way of starting a conversation. Probably joking back is wht he expects from you. Of course, he's probably open to suggestion if you decided to drop your current flame...!
I do this regularly although I'm married, just for example.
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I do but I'm an incorrigible flirt. And when I say I do, I mean with women who are my friends...I know them and they know me. I'd be far more reluctant to do so with a woman I didn't already know pretty well. To me, there should be some form of 'permission' given by her first.
What kind of comments does he make? He could just be flirting...no harm in that.
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