Reader Mailbag: Escaping The Small Talk Trap

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It’s been too long since our last reader mailbag, so here we go. The emails have piled up to an unmanageable level, which means if you don’t see your question answered here, stay tuned for future reader mailbags.
Email #1 is from a reader who wishes to remain anonymous. The Niceguy’s Lament:
Dear CH,
They say the first step to fixing a problem is recognizing there is one. My problem is this: I’m a gamma. I’m 23, unkissed, I’m often called a nice guy and been rejected numerous times as a result. I fall into the trap of

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