Sit right next to him, maybe even bump into him and nudge him a little bit in a friendly way. Should help a little bit.
As someone who started super shy and overcame it, I found it helpful in the beginning to connect physical actions to words. For example, back then the prospect of introducing myself to people at a party was so daunting, until I learned to look at it as a series of physical actions: "Put one foot in front of the other until you are in front of a person, then extend hand out." Then I'd follow the physical directions and be standing in front of a person with my hand out, and now I better introduce myself or I'll look like a crazy person! And then the words came.
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I used to be shy too, so I get where you're coming from. Take a deep breath, spend a point of Willpower and just talk to him.
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