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My friend and I agree, if a man gets a whiskey sour without a cherry, he's okay. One of our machismo friends orders these all the time. He's a playa.

ScottieK

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Whiskey sours taste great, but the high sugar content sometimes gets a little tough to take after a few.

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I agree, I can only handle about two or three.

I don't however think it's a particularly masculine drink. B/c of the sugar and the cherry/fruit that often comes in it. I couldn't imagine ordering one and explicitly asking the bartender to hold the cherry. Seems ridiculous.