How do I get talking to this Chinese guy without looking strange?

Become a regular. Try to figure out where his tables are so you can sit there. If you can figure out which tables he waits on then you can do small talk while you order. Like when he first comes to get your drink have a small conversation before ordering. ask him how he is or something. Small talk. Then hen he brings you your food or drink always that thank him and give a shy smile. Hope this works for you.