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Well, I would curb the matchmaking urge and just make sure he knows youre his solid friend. Sounds to me like a relationship with either gender isnt his main problem or magic solution. A girlfriend or boyfriend cant fix it. He's got to solve it, there maybe lots of reasons why hes not coupled up, and single can be just fine. I'd watch for signs of depression, and offer the support you can.
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Yeah! What she said. 
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The descent of man ~ Nixon, Friedman, Reagan, Trump.
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