What Is Dating in Manhattan Like for Men?

Dating in Manhattan as a man is dense, quick and expensive. It is the smallest of the five boroughs and the most crowded. Women are on every block, a coffee shop and a bar are always a short walk away, and a first meeting can turn into a date within minutes. The other side is speed. People walk fast, schedules are packed, and the man who waits to be noticed gets passed over.

Here is what the borough is like from a man's side, neighborhood by neighborhood and hour by hour.

Manhattan is the most densely populated of New York's five boroughs and the smallest by area. Its borders are the same as New York County's, which is the smallest county in the country by area.

For dating, that density is the whole story. You can walk from a park to a bookstore to a wine bar in fifteen minutes. a dating coach puts it this way: "wherever you are there's a coffee shop, a bar, an ice cream place and a restaurant within a couple blocks walk." That makes a spontaneous date, right after you meet, easier here than almost anywhere.

Each part of the island has its own crowd and its own rhythm.

Midtown is offices and tourists. The sidewalks are the fastest in the city, so the places where people sit down, such as Bryant Park, matter more than the streets themselves.

The Financial District is full of young professionals on weekdays and quiet on weekends. After-work drinks are its strength.

The Villages and the Lower East Side hold much of the city's nightlife. The East Village and Lower East Side are dense with bars, while the West Village is smaller-scale, with wine bars and streets that wander off the grid.

Chelsea and the Meatpacking District mix galleries, the High Line and dressier nightlife.

The Upper East and Upper West Sides are more residential. People there tend to be a little older, more settled, and out for dinner rather than a long night.

By day, the best places are parks. My list for Manhattan is Washington Square Park, Bryant Park, Madison Square Park and Union Square Park, with Central Park usable but too big to be his first pick. Women sitting in a park have time, and as coach puts it, "if someone's out in a park they've come out to be among people."

By night, coach describes three tiers. The first is ordinary bars that anyone can walk into, which are full and easy. The second is selective clubs with a door policy, where getting in takes some effort and the mix of men and women inside is better for it. The third is very exclusive clubs, which take money or connections. A man starting out does fine in the first tier. In warm months, rooftops are the best of all, because the open air keeps the music low enough to talk.

Many bars stay open until four in the morning, and coach notes that the end of the night is when many women are still out without their friends.

The biggest advantage of living in Manhattan is that other people will come to it. My experience is that it is easy to get a woman to come into Manhattan, especially lower Manhattan, and hard to get her to leave it for the outer boroughs.

His ideal base is anywhere below about 60th Street. He says he would take a small, cramped place in a good location over a nicer place farther out, because where you live decides how easily a date happens.

Most first dates in Manhattan are a drink or a coffee, followed by a walk to a second place nearby if it is going well. Nobody expects dinner on a first date, and a long sit-down meal can trap you before you know whether you like each other.

The subway and cabs also mean people rarely depend on a ride from friends. coach points out that women in New York often arrive and leave separately, which makes it easy for a good conversation to continue somewhere else.

Manhattan is expensive. Drinks, dinners and cover charges add up, so keep early dates simple. It is also loud in the big clubs, rushed on the sidewalks, and crowded enough that people put up walls with headphones.

None of this stops anyone from meeting women. It just means picking your moment: the woman on a park bench, the woman browsing a bookstore, the woman at the bar who is not in the middle of a conversation.

Cold Approach runs its Bootcamp in person in Miami and New York only. In New York it is arranged with you after you book: Private runs one, two or three days with your coach alone, and Group, with no more than three students per coach, is available on request. Each training day is two four-hour blocks in the field, with daygame and night game mixed to suit you, live coaching on every approach and feedback after every set. Beginners are welcome, and you leave with a written practice plan.