Where Should You Take a Woman on a First Date in NYC?

Take a woman on a first date in NYC to a bar you already know, near where you live, quiet enough that you can hear each other without shouting. In Manhattan that usually means a small cocktail or wine bar on a side street, not the loudest place on the avenue. If you met her in person, pick somewhere within a few blocks of your own place or of where you approached her, and keep a second spot in mind a short walk away.

A bar lets you sit close, order one drink or three, and leave whenever you like. A restaurant does none of that. a dating coach is blunt about it: "do not take a girl to dinner on a date if you can avoid it." At dinner the table sits between you, the courses set the pace, and if the evening is going well you cannot simply get up and walk somewhere else.

The same goes for a movie or a comedy show, where she spends the night looking at a screen or a stage. A chain coffee shop is better than either, but My advice for that case is to treat it as the start of the date and then move to a real bar.

Pick the evening over the afternoon. coach prefers a date at eight thirty at night to one at eight thirty in the morning. Evenings carry the sense that something fun might happen, and the places open at that hour feel more like a date.

New York is big, and a first date that needs an hour on the subway starts tired. My rule is to hold the date near your place if you can, near hers if you cannot, and never in between: "Going in the middle is the worst."

He also notes a quirk of the city. A woman will happily travel into Manhattan, but it is much harder to get her out to the outer boroughs. If you live in Williamsburg or Park Slope and she lives in Manhattan, a bar in your own neighborhood is still the right call. Just make it easy to reach, near a subway stop she can use.

Once you find a bar that works, keep using it. In My words, "it is okay to go to the same place over and over again." The bartender knows you, you know which seats are quiet, and you never have to guess whether the music will be too loud.

These two neighborhoods hold more small bars per block than almost anywhere in the city. Many are dim, cramped and good for sitting close. That density is their big advantage: a second bar, a late slice or a walk is always two minutes away.

The downside is the weekend crowd. On a Friday or Saturday night, the best spots are packed with bar-hoppers and some have lines. Go on a weeknight, or go early, and pick a place with seats at the bar or small booths rather than a standing room.

The West Village feels made for a first date. The streets are crooked and quiet, the wine bars and cocktail rooms are small, and the whole neighborhood is easy to walk. When you are ready to move, Washington Square Park and the Hudson River waterfront are both close.

It does cost more than the Lower East Side, and the best tables fill up. A weeknight evening is the sweet spot.

The Upper East Side is calmer and more residential. Its bars lean toward neighborhood wine bars and old taverns, with an older crowd and earlier nights. It is a good choice if either of you lives uptown, and Central Park is a few blocks away for a walk before or after.

Murray Hill has a reputation for a younger, post-college crowd and sports bars that get loud on weekends. For a first date, choose one of its quieter bars on a weeknight, or treat it as a starting point and walk somewhere calmer.

The best first dates in New York move. You meet at the first bar, the evening goes well, and you suggest one more place nearby. Mention early on that there is another spot you like around the corner. If she likes the idea, the move feels natural when it comes.

Choose the second place before the date. In warm weather, a rooftop is a strong option, since the open air keeps the music down. In winter, a small bar with a fireplace or a quiet back room does the same job.

Not every first date in New York is planned. coach points out that in this city, "wherever you are there's a coffee shop a bar an ice cream place and a restaurant within a couple blocks walk." If you meet a woman in a park or a bookstore and the conversation goes well, suggesting a drink around the corner right then is often easier for her than agreeing to a date next week.

Recognizing when an immediate date makes sense is part of what the Cold Approach Bootcamp trains. It runs in New York and Miami. Each training day is two four-hour blocks in the field with a coach, with daygame and night game mixed to suit you and feedback after every approach. Group is three consecutive days with no more than three students per coach, and Private is 1-on-1 for one, two or three days. There is no skill floor, and you leave with a written practice plan.