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Rather than pinning all of your hopes for him getting out and about on this one friend who kind of sort of doesn't get along with him, why don't you guys try some activities that are free but that allow you to meet people with similar interests? Volunteer organizations are great for that, and reading groups, too. I can't think of other examples offhand, but those two might help.
As for bringing up how he interacts with your friend, you might just say "she's a little sensitive, so could you try being extra nice to her?" or something like that.
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"If ten million people believe a foolish thing, it is still a foolish thing."
- Anatole France
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