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Depends. At a meh bar with bar food, probably an IPA. Mexican place with Mexican food, probably margarita or tequila sunrise. At a cocktail bar, I’ll pick a signature cocktail, probably one with a whiskey of some kind. If it looks like they know what they’re doing but they focus on botanical type stuff (which I don’t really like), then I’ll usually go for something like an old fashioned or a Manhattan, and if it’s not too busy I might request it with the bartender’s choice of unique flair on it. Or I might order a carajillo if they have an interesting one on the menu and if I see an espresso machine.
I’m genuinely not sure whether this is a teachable skill or something more like a character trait.