Always look for the locals' bar like Sunny's Bar in Red Hook

When it comes to striking up a conversation, no one knows better than a bartender.

Tristan Willey, of Brooklyn’s Long Island Bar, is as well versed in the art of conversation as he is in the art of cocktail making. So who better to advise travelers on the fine art of drinking solo? 

“Avoid opening lines. It makes for a better interaction. One of the best parts about being alone is that you’re not forced to interact, and you can wait for the right moment to strike up a conversation. The world gets to revolve around you for a little bit when you’re sitting alone at the bar, and usually a natural entry point comes along. You shouldn’t force it.

“In New York, so many travelers have this idea of what the city should be like. They try to react to that idea instead of taking the time to absorb the scene of the individual bar. So it’s really wonderful when you have a solo person come in and just enjoy where they’re at for a bit and try to understand it for what it is.

“When I travel, I like going to local bars, because you get to see people who are living nearby, drinking casually. You get to know the community so much better when you’re not at the kind of destination bar that people treat as an event. My favorites in New York are Brooklyn Inn in Boerum Hill and Sunny’s in Red Hook.

“Finding places like those is hard, though. I tend to start with a bar that’s stuck in the middle of a neighborhood. All the bartenders you’re talking to live nearby. Order a pint of beer, talk with them. Ask them where they drink, and take their advice.”

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