Maybe he's trying a new tactic to get you on his side. Since his "way" is so alien to you, you didn't pick up on the motivation and it seemed weird ?
I have a sense that this was just another in his series of attempts at witty banter, and he's just oblivious as to how lame they are.
The last few suggestions would be a 'hit on' thing.
Comments can have a sexual tint to them without being a pick-up attempt. In this case I think it was just trivializing and dismissive, without being sexual on top of that.
It sounds like he desperately wants to be liked. And you do not like him.
I hadn't considered this.
I have been feeling like the ousider... he's known many of my co-workers for ages, and I have been feeling insecure all over again. It hadn't occurred to me that maybe he's feeling insecure as well.
-k
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