Demanding a raise: Impossible to pull off smoothly?

Question: “It’s been three years since I got a raise and I need to have the discussion with my boss about it. If I can’t get one, I think it’s time to move on. But approaching him about it feels so awkward, no matter what technique I imagine. Requesting a meeting will make that awkwardness hang over our heads until it happens, but I just know approaching him casually will make me scramble for lame words. Is there a painless way to do this that doesn’t put us both in an uncomfortable spot?” – Erin, Restaurant Marketing Assistant

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