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Ok Generally:
Well . . . a lot of what girls think is game playing is actually insecurity or a lack of finesse.
Ever feel bad about yourself one day and not want to run into the guy you are crushing on? Well guys are the same way.
Plus the first few seconds of every encounter determines how we react. So if he looks at you and you are frowning or expressionless he might read something negative into it and abort his approach. It depends on how he is feeling about himself.
Its that whole passive agressive approach/avoidance thing.
You beckoned him over to join your group, and he beckoned you over to join him, he was probably being playful but when you didn't come over he may have thought it was a lack of interest or maybe he didn't want to interact with your friends. Or ask you out in front of them.
A little more specific:
The one thing I don't undertand is that he has inside information to work with. A go-between. Those things are awesome. Great ice breaker. So he knows you'll say yes. If he can't muster up the courage then, who needs him? Especially if you aren't real into him anyway.
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