Questions: Guy's Behavior

I've always wondered this...

How do you all feel about it?

I’m quite close to a guy at work. He is 27 and I’m 29. I’ve known him for a couple of years and we get on really well. He is very playful around me.

Recently he’s done a few things which caught my eye. We were talking about plastic flash, and then he starting talking about flashing. I think he said something like “I hope you don’t start flashing” but he had a little smile on his face.

Then today, I said to him “would you prefer it if I cancelled my vacation for you” to which he said yes. And then later he was jokingly moaning about me going on vacation. I said, “just because you’re going to miss me” and he had a little smile on his face but said nothing.

He said I looked vicious. I asked him if he thought I looked scary - to which he replied “terrifying”