How to get more personal with my crush? It's a long one?

I'm crushing hard on a guy I work with (I have dated coworkers before with no issues, he's in a different department, and our company is perfectly fine with coworkers dating - in fact, we have many married couples!). I get the feeling that he's interested in me too, but I'm not sure, and that's mostly because ALL WE DO IS JOKE. All day long we kid around on the messenger sending each other memes and adopting silly personalities. Every once in a while we have a conversation that includes our personal interests, but that usually includes something about my cats or his siblings, and it always ends up a joke. There really is nothing serious about our relationship, but it can get rather flirty (on Facebook) with one of us ending with a joke about being lonely. We have been "chatting" daily for about a month now, and he introduced himself to me by bringing me fudge about six months ago.

We are both introverted and have been in serious relationships before, so the idea of dating again and making a serious move can be intimidating I think to both of us. I am afraid to make a move because he might reject me, and I think he might be in the same position. He is usually the one to initiate contact with me throughout the day, even when a joke is over. We have the same senses of humor, which is good, and although I don't know if we have a lot in common or not, I know we have the same core thought processes and personality traits, which makes our relationship so easy with natural chemistry.

I would really appreciate some advice on how to get to know him better and really see who he is and if he is "worthy" of my crush, so to speak. I'm not so silly that I want to marry this guy without knowing him! I mean honestly, we don't ask each other "what's up," or "how are you," such basic questions to get to know someone. And at this point, my social anxiety prevents me from actually asking him anything personal. I know he suffers from it too. Does anyone have a similar story?
How to get more personal with my crush? It's a long one?
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