Issue No. 1

I Have Six Homes. Do I Really Need a “Matchmaker Near Me”?

By Patti Feinstein

Dear Matchmaker,

Dear Matchmaker, I have six homes. I divide my time between Florida, New York and wherever business or life happens to take me. And apparently, finding one matchmaker is harder than maintaining six houses. I've Googled "matchmaker near me." I've asked Siri. I've asked Alexa. I've asked ChatGPT. I've even tried Gemini. Everyone can tell me where to find a matchmaker. Nobody seems able to tell me how to choose the right one. When I'm in Sarasota, I'm told I need a Sarasota matchmaker. When I'm near Boca Raton, suddenly I need a Boca Raton matchmaker. When I travel, the recommendations change all over again. Am I really supposed to hire a different matchmaking company everywhere I own a home? I'm not looking for six matchmakers. I'm not even looking for six dates. I'm looking for one person. How do I find a matchmaker who understands that? — Looking Everywhere

— Signed, Looking Everywhere

Dear Looking,

You have six homes?

Then I can save you at least one search.

Stop typing "matchmaker near me."

Near which home?

You've asked Google, Siri, Alexa, ChatGPT and Gemini where to find your matchmaker.

I'm going to suggest something decidedly old-fashioned:

Find the human being you trust to find another human being.

Traditional Matchmaking vs. Executive Matchmaking

Many brick-and-mortar matchmaking companies operate with large databases of singles.

That isn't necessarily a bad thing. That model works very well for some people.

But you should understand what you're buying.

You may meet one person during the sales process and work with someone entirely different after you join. Your matches may be selected from a large database, and the matchmaker arranging your introduction may never have personally met both of you.

Executive matchmaking is different.

It's smaller. More personal. More curated.

Your matchmaker should actually know you.

And just as importantly, your matchmaker should know the people being considered for you.

I want to know more than someone's age, education, profession, height and ZIP code. I want to understand personality, presence, lifestyle, relationship history, values, attraction and all those little things you simply cannot learn from checking boxes on a profile.

That's the difference between matching data and matchmaking people.

And if the right person isn't already sitting in a database?

That's when the search begins.

What If the Right Person Doesn't Live Near You?

Let's say you live in Sarasota.

While everyone—and I mean everyone—would love to meet the one in their own backyard, the right person might just live near Boca Raton.

Or Naples.

Or maybe they live where you spend your summers.

Your primary residence may be in Sarasota, but your life isn't necessarily confined to Sarasota. You travel. Perhaps you have another home. Your business takes you between cities. You may spend part of every year somewhere else.

So why would you automatically limit one of the most important searches of your life to your immediate area?

A good executive matchmaker shouldn't simply be asking:

"Who do I have near Sarasota?"

The better question is:

"Where is the right person for you?"

Maybe that person is in Sarasota. Wonderful.

But if the person who truly fits your life is near Boca, I'd rather make that introduction than limit your search simply because someone else happens to live closer.

Convenient isn't the same thing as compatible.

People Move Mountains for Love

There's an old saying, and after decades in matchmaking, I can tell you it's true:

People will move mountains when they find love.

Before they meet that person, they'll give you every reason they can't move.

Their business is here. Their family is here. Their house is here. Their golf club is here. Their life is here.

Then they fall in love.

Suddenly, they're figuring it out.

That doesn't mean geography isn't important. It absolutely is.

But I would never assume that where someone lives today determines where they're willing to build a life tomorrow.

Does Executive Matchmaking Cost More?

Sure.

Personal service usually does.

A truly curated matchmaking search requires time, discretion, recruiting, networking, screening and actual human judgment.

But instead of simply asking:

"How much does a matchmaker cost?"

Ask:

"What am I actually paying my matchmaker to do?"

Are you paying for access to a database?

Or are you hiring an experienced professional who knows you personally, understands what you're looking for and is willing to search for that person?

Those are two very different matchmaking experiences.

How Do You Choose the Right Matchmaker?

Before hiring a professional matchmaker, find out who will actually be handling your search.

Will you know your matchmaker personally?

Does your matchmaker personally know the people being introduced to you?

Can the search extend beyond an existing database?

Can candidates be recruited specifically for you?

Can your search move with your life—from Sarasota to Boca Raton, Naples to Miami, Florida to wherever you spend your summers?

And when your matchmaker calls and says:

"I have someone I think you should meet."

Does that person actually know why?

Because you don't need six matchmaking companies for six homes.

And you don't necessarily need the best matchmaker near you.

You need the best matchmaker for you.

— Patti Feinstein Executive Matchmaker

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