How do you deal with liking a SHY guy?

I'm definitely out of my comfort zone here.

I'm not an extrovert by any means necessary, I am entirely introverted, but still I find it hard to flirt with this man.

As of late, the flirtation has shown to be mutual. But I had to put the work in. And I would feel weird as fuck bc I didn't know if he was just smiling top be nice and thinks I'm a fucking weirdo or if he is smiling back and reciprocating bc he's interested.

How the hell do you tell the difference!?

I'm 33 and he's 38

I've have NEVER seen myself liking a shy dude, especially being my ex was a confident ass dude so it's just weird

My dilemma is how do I know when far has gone way too far?

I'm straight forward, blunt and honest

So if someone isn't being direct with me, I can't figure out what they want/don't want

Thoughts on this?