How do I talk to a shady coworker?

Okay so he’s really my boss but I noticed he can be a little shady sometimes. Even after he’s shady he still tends to smile in my face and wave excitedly but also if I told speak back to him he won’t go away unless I speak to him. I never gave him any signal to make him think we are close or that friendly with each other. He’s more closer to the coworkers he’s shady with but still speaks to me, I speak back most of the time but he tries to hold an entire conversation with me but I have no desire to speak to him.

How do I talk to a shady coworker?
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