What Are Good Date Ideas in Brooklyn?

The best date ideas in Brooklyn use the borough's walks and small bars. Think of the skyline view from the DUMBO waterfront, a quiet bar in Williamsburg or Greenpoint, an afternoon in Prospect Park, or the Coney Island boardwalk when it is warm. Pick somewhere close to where one of you lives, since crossing the borough by subway eats the evening. If you met her in person, a drink or a walk a few blocks from where you approached her is the easiest yes you will get.

Brooklyn is the most populous of New York City's five boroughs, and its best-known view looks back at Manhattan. Walk Brooklyn Bridge Park in DUMBO in the early evening, when the skyline lights up across the water, then stroll up to the Brooklyn Heights Promenade.

This works as a first date because you spend it side by side. Walking takes the pressure off, and the view gives you both something to react to. Finish at a bar or a wine spot under the bridge, or keep going if the night is good.

It is also the one Brooklyn date a woman from Manhattan will happily travel for. The walk over the Brooklyn Bridge is part of the evening.

Williamsburg has more bars per block than anywhere else in the borough, from rooftops with Manhattan views to dim cocktail rooms. Pick one quiet enough to hear each other, and keep a second place in mind a block or two away.

In daylight, Domino Park and the East River waterfront are good for a walk, and in the warm months the weekend food market Smorgasburg turns lunch into an easy date with lots to try.

Greenpoint, just north, is calmer. Its bars are smaller and its streets quieter, which suits a man who wants the date to feel low-key. McCarren Park sits between the two neighborhoods if you want somewhere to walk.

Prospect Park is the best daytime date in Brooklyn. Bring coffee, walk the Long Meadow, and sit by the lake if the weather is good. In spring, the Brooklyn Botanic Garden next door is famous for its cherry blossoms, and the Brooklyn Museum is a few minutes away for a rainy day.

Afterward, Park Slope has plenty of bars and cafes along its avenues for a drink. A daytime date also tells her you are not only interested in a late night, which makes it an easier yes for some women.

For a more unusual date, walk the street art of the Bushwick Collective. The murals change often, and the area has bars and music venues to end the walk.

In summer, Coney Island is a classic. Ride the Wonder Wheel, walk the boardwalk, and get something cheap to eat. It is a long subway ride from most of Brooklyn, so save it for a second or third date, when spending a whole afternoon together makes sense.

Brooklyn winters push dates indoors. Try a bar with a fireplace or a back room, or a bowling alley or arcade bar where your hands have something to do. A small music venue works too, and so does a museum visit followed by a drink.

Skip the long dinner. a dating coach's advice is plain: "do not take a girl to dinner on a date if you can avoid it." A table between you and a waiter setting the pace make the evening harder, not easier. A movie has the same problem, since she spends two hours facing a screen.

The easiest dates are near where one of you lives. My rule is to stay near your place if you can and near hers if you cannot, because "going in the middle is the worst." A date in Greenpoint when you both live in Bushwick and Bay Ridge means two long trips and a tired evening.

Brooklyn is big. Before choosing an idea from a list, ask yourself which neighborhood keeps the trip short for both of you. Then choose a place there you already know.

Some of the best Brooklyn dates are never planned. You talk to a woman in a bookstore in Williamsburg or a cafe in Park Slope, it goes well, and you suggest a drink around the corner right then. In a walkable borough, that 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, in person 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.