Tips for dealing with a shy guy?

Seems he is OK as long as he makes a "move" (smiling, waving, trying to hit me with his car). And he always seems happy to see me (the majority of the time). He does not like seeing me talking to other guys (they were all that was in our training class at work it's not my fault I know a lot of guys at work).Seems to really like eye contact as long as he intiates and not I. And seems to want to talk if I start the conversation. But if I smile, wave, or anything at him first he freaks out. I say this because he either looks the other direction and then avoids me, or he looks like I tortured someone to death in front of him, and then avoids me. I really have no idea how to make this move anywhere if I have to be the one in charge, but he can't handle it?
Updates:
I should mention that I assume he likes to talk to me. He seems very helpful (I ask for advice mostly, you know to instill confidence) tells me a bit about himself, and is fidgety at times.

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  • You need to be assertive if he's shy

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    • Thanks, but considering I apparently did something to make him mad and I do not exist in any way anymore it doesn't really matter.

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