Where Can a Man Meet Older Women in NYC?

Meet older women in New York where they actually spend their evenings and weekends. That means wine bars, hotel bars and quieter lounges, gallery openings and museum nights, classes, and the parks during the day. They are rarely in the loud bars built for people fresh out of college, so a man who only goes where his own age group goes will barely cross paths with them. When you find her, approach with a plain, adult hello, and let the age difference be the least interesting thing about you.

Most women in their late 30s, 40s and 50s spent years in crowded, cheap, loud bars. Many have no wish to go back. When they go out, they want somewhere they can sit, hear each other and order a drink that is not served in a plastic cup.

That is why the usual weekend bar crawl misses them. You can spend every Saturday in the busiest rooms on the Lower East Side and rarely talk to a woman over 35. The fix is not to try harder in those rooms. It is to change rooms.

Wine bars and cocktail bars. A quieter room with good drinks and seats at the bar draws an older, better-dressed crowd. Sitting at the bar is the key. It puts you shoulder to shoulder with whoever is next to you, and the menu hands you an opener.

Hotel bars. The bars in the city's better hotels mix travelers, locals and people meeting friends after work. A woman in town for business, sitting alone with a glass of wine, often welcomes a friendly conversation.

Lounges with a bit of a door. a dating coach's favorite tier of New York nightlife is the semi-exclusive room, harder to get into than a dive and easier than the most famous clubs. He finds the women there more successful on average, and the room has more mingling and less table service than the top clubs.

Restaurants with a real bar. Plenty of women eat at the bar alone or with one friend after work. It is one of the most relaxed places in the city to start a conversation.

New York is packed with galleries, museums and talks, and older women use them. Gallery openings in Chelsea, members' evenings at museums, lectures and readings all bring out an educated crowd with something to talk about. You have a built-in opener: the thing you are both looking at.

By day, the parks work at every age. A woman reading on a bench in Madison Square Park or walking through Central Park on a Sunday has stopped on purpose. Farmers markets, bookstores and the paths along the rivers do the same.

a dating coach suggests yoga, pilates and social dance classes as reliable places to meet women in New York, and those classes draw women of every age. Cooking classes, wine tastings and language groups do the same. The weekly format helps you, because she gets to know you over a few sessions before you ever ask her out.

Older women tend to read men quickly. A few things make a big difference.

Go to her when she is alone or with one friend. In a group, her friends are more likely to look sideways at a younger man and make her feel self-conscious, even if she likes you. On her own, she decides for herself.

Act your age, and act like a grown-up. A man who is calm, direct and has a life of his own comes across as mature at 26. A man who is nervous, jokey and trying to impress comes across as a boy at 36. Dress a level up from what you would wear to a regular bar.

Do not make the age the topic. Asking how old she is in the first minute, or joking about the gap, turns the conversation into a story about a number. Talk about the gallery, the drink, the city, her week.

Be clear. If you like her, say so and ask for her number. Many older women have little patience for a man who hints for an hour and never asks.

Leave the labels behind. Calling her a cougar, even as a joke, tells her you see her as a type. So does treating her like a trophy or an adventure. She wants to be met as a woman you find interesting, not as a category you are curious about.

The places above put older women near you. Starting the conversation is still up to you. Cold Approach runs its Bootcamp in New York and Miami, with two four-hour blocks in the field each training day, daytime approaches and nightlife mixed to suit you. A coach watches each approach and tells you what to change. A Private Bootcamp is 1-on-1, so the days can be built around the kinds of places you want to practice in.