One additional point- not that you should change or compromise your own values on the topic, but we eventually "caved" and got a gaming system. It helped our DS tremendously, as it gave him an "in" and helped him connect with other boys. So much of the culture here, at least in his age/gender group, seemed to relate to this. While we choose games selectively, there is still enough common ground that he can be part of the conversations happening at school, and feels more comfortable inviting boys over, even if they don't end up playing games (which is frequently the case). We are probably atypical, in that the game console is very infrequently used, but for the above reasons it has been helpful.
That said, I agree with zs, that this issue is probably more about social skills than the specific media; sounds like your DS is trying hard to connect but could use some help figuring out more acceptable ways to go about it.
