A guy told me I'm pretty cool and that he enjoys chatting with me.. And
When we don't chat he misses chatting with me.. Not what I should think

Do you know if he is in a relationship? If so, then being a friend or leave him alone are your options.

How do you feel about him? Do like chatting with him? Do you want to ask him out and see where it goes from there?

He may just be saying that you're a good friend who he enjoys being around. He may be getting up the nerve to ask for a date. Only way you will know for certain is to ask him.

I think it depends what you talk about.

Do you talk about everyday things... what you've both been doing,where your going out next, your family etc... or does he mention relationships he's been in, how they worked out, what went wrong and so on.

Maybe he just feels at ease with you.
Most of us have someone that we have as a friend who we know we can say what ever we like, whether it be advice on the latest guy/girl friend, or just something simple like, could I wear this dress with these shoes etc...

He could be leading up to asking you out, just wants to get to know you first,listen to what he says and take your lead from him.

However, if you choose to speak up first by asking him out and that is not his intention, then you may spoil what you have as friends.

I think you enjoy the chats, and don't get carried away, or jump to conclusions. No telling who is on the other end.