Shall I ask him out?

So there is this guy. He is 1 year older than me, we studied in same law school, participated in same moot competition, he was my team coach once...
Now we work together.
I have suddenly realized I really want to be with him. We are very good friends. 
Shall I ask him out? How to make him understand I want to move to another level?... For reference, we go out, chat, but flirty texting is hard with him - he is not a social network guy:)))) starting with texting could be the easiest.... Shall I ask him to movies? To me? Just randomly kiss him?? He is not even ever drinking, so tipsy make out is not an option....
Ps deep inside while writing this text I have understood I'm just looking for encouragement to ask him out:))

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