How to Get Guys to Buy You Dinner in Brooklyn

By Amber Castello

I’m going to tell you how to get free dinners from guys.

If you’re a guy, you should read this so you know how to not get used. If you’re a girl, you should read this so you can find some extra spending money.

But first, let me tell you my story. I am 32 years old, blonde, live in Bushwick. Honestly, I can start a conversation with just about anyone. But you don’t really have to look like a model to get a guy to buy you dinner in Brooklyn. You just need to find a tourist.

And to do that, you go to places where tourists visit.

New York Tourists will Pay to Hear your Story

Guys that hang out at tourist spots want to meet a real New Yorker, so when they meet me (and hopefully you), they are usually in a hurry to woo you. That means, they want to buy you dinner.

Want proof? I promise this is a true story from Peter Lugar Steakhouse. For those who don’t live in Brooklyn, this is prime tourist real estate.

It was a Tuesday night (pre-pandemic). I looked pretty good after my sales meeting, so I didn’t want to call it a night too early, so I headed to the bar in Williamsburg.

After a glass of wine that I bought myself, I started talking to a gentleman. I later found out he was married, but that’s okay because he was a nice person to talk to and had an expense account.

He treated me to a glass of wine, and it didn’t take long before he started opening up about when he met his wife. He told me about their struggles and how they had no money when they started out.

It was an enjoyable conversation as we jockeyed for position at the bar to grab a bite to eat for dinner. Roughly 30-minutes later of listening to his life story, in walked Bill – a 75-year-old man wearing a traditional Southern suit and a University of Texas pin.

3 Tips to Get a Stranger to Buy you Dinner

So how do you identify which men will buy you the dinner? Pay attention to the details. In that situation, I paid attention to the University of Texas pin, commented on it with a flirtatious smile, then leaned in and touched his tie.

He bit. He was on the line and dinner was within my grasp.

Here is tip number one – pay attention to the key players. If you want a free dinner, you need to identify men by themselves, wearing a suit. An accent will increase your odds, or an obvious sign that they are from another city or country.

Tip number two – don’t forget who brings you to the dance. In the above story, I never left out the married man. In fact, I invited the married man into the group and conversation. Be a team player if you want to get free food.

Tip number three – Let the leading man lead. This is a good tip that most women don’t follow. In the case with our Texan Bill, he asked me, “What wine do you want?” I said, “you look like a well-traveled man, so I’ll let you pick your favorite. Or should I call over the sommelier?”

Men who buy dinner typically are leaders. They are the ones who are closing the deal and bringing in the money. You don’t want to challenge a leader if you want a free meal. Many New York women are type-A and that is their mistake. They want to show they can buy their own dinner. Good for them.

Tip number four – don’t be afraid to order what you want. A man like this wants a confident woman who knows what she wants. You secretly are the one in charge. Treat yourself, you deserve it. In the case with Bill, I ordered a $50 steak.

Women will criticize, men will scoff, but it’s okay. I don’t feel guilty. I met some great new people, we had a great conversation, learned something new about life and of course, I got a great dinner out of it  without paying a dime.

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