From the way you tell your story, I presume that you would not mind if the situation develops into something more than just casual meetings, right?
If that is the case, then you should not beat around the bush and make you intentions known to him. Without taking any risk, you will not achieve anything and your relation will remain platonic.
I suspect that he is either shy or has had previous bad experiences with previous relations.
You could casually lead the conversation on more personal topics such as
1. how does he feel about being romantic
2. if he would reject a kiss from you
3. what he thinks of a romantic dinner
4. if he would like to take a long week-end with you away from home
There are many different hints you can throw his way. Depending on his reaction or replies, you should be able to analyze the situation and whether it is to your advantage or not.
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I‘d start by asking where the two of you stand
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Ask him straight out what he wants
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