Why High-Value Men Rarely Start With Dinner (And Why That’s a Good Thing)
I’ll never forget one of my favorite clients.
It was a few years ago...
She lived in Miami, was 31 years old, incredibly beautiful, fit, funny, kind, and had built a large food wellness brand. She came from a wonderful family, had unlimited options, and frankly, could have dated almost anyone she wanted.
But there was one problem.
Most men she met simply weren’t comfortable dating a woman who had achieved that level of success so young.
She wasn’t looking for “a successful guy.”
She needed someone operating at the same level... someone who understood entrepreneurship, wealth, responsibility, and what it takes to build something extraordinary.
Those people are rare.
Very rare.
As her matchmaker at Cinqe, we searched across the United States, introducing her only to entrepreneurs, founders, family office executives, and men who had built significant businesses themselves.
Then one day, I got the call.
The Least Romantic First Date Ever
One of the men we wanted her to meet happened to be a paying client of another matchmaking company.
People are often surprised when I tell them this, but it’s true:
We work with other matchmaking services ALL THE TIME.
Why?
Because your perfect match may already be paying another firm.
Good matchmakers collaborate.
That’s how more great introductions happen.
This particular gentleman was extremely private and high-profile. I couldn’t send photos or share much information.
I simply called my client and said:
“You gotta meet him... he’s the real deal.”
Then I gave her the details.
He only had one opening.
Wednesday.
3:00 PM.
Tea.
In Los Angeles.
No dinner.
No fancy restaurant.
No glamorous evening.
Just tea (they both didn't drink anyway).
She Understood the Assignment
Some women would have immediately said:
“If he’s serious, he’ll take me to dinner.”
She didn’t.
She booked the next flight to Los Angeles.
She understood something that many people miss.
A man who has spent decades building a successful business doesn’t protect his money nearly as much as he protects his time.
His calendar is his most valuable asset.
Offering someone two or three hours over dinner before even knowing if there’s chemistry isn’t always practical.
It doesn’t mean he isn’t serious.
It usually means he values his time because that’s exactly how he became successful in the first place.
So she met him for tea.
They talked.
They laughed.
There was chemistry.
That evening…
He invited her to dinner.
The next day…
They spent more time together.
At one point, he even took her for a helicopter ride (true story)
Six months later…
They were engaged!!!
Every part of that story is true.
Ladies, Stop Judging the First Date
One comment I hear all the time is:
“If he asks me to coffee instead of dinner, he’s cheap.”
In my experience after more than 16 years as a professional matchmaker…
That’s often the exact opposite of what’s happening.
Many of the wealthiest men I’ve worked with have suggested coffee, tea, or a quick drink for a first meeting.
Not because they couldn’t afford dinner.
Because they’re deciding whether the two of you deserve more of each other’s time.
Think of it this way:
If you were interviewing someone to become your business partner, would you immediately block off your entire evening for someone you've never met???
Probably not.
You’d have a meeting first.
Dating works the same way.
And Ladies… Why Give Away Your Dinner Spot?
Here’s another way to think about it.
Why are YOU so willing to give a complete stranger your entire evening?
Your time matters too.
If dinner is your favorite time to relax, unwind, or see friends…
Why not let someone earn that spot?
A great first meeting should simply answer one question:
“Do I want to see this person again?”
That’s it.
Nothing more.
Nothing less.
Coffee Dates Remove Pressure
One thing I’ve learned after introducing thousands of people is that coffee dates create better conversations.
They’re shorter.
They’re easier.
No one feels trapped.
If the chemistry isn’t there, both people can leave after 20 or 45 minutes.
If the chemistry is incredible…
You can alwaaaaaays continue.
Many of the best relationships I’ve seen started exactly this way.
My Advice After 16 Years of Matchmaking
Ladies…
If a great man asks you to coffee…
Go.
If he suggests tea…
Go.
If it’s a quick afternoon meeting…
Go.
Don’t let the location determine the quality of the opportunity.
Judge the man.
Judge the conversation.
Judge how he makes you feel.
Not whether he ordered espresso instead of filet mignon.
And gentlemen…
Don’t let anyone shame you into believing coffee is somehow “low effort.”
Meeting a complete stranger over coffee or tea is smart.
It’s respectful of both people’s time.
And if the chemistry is there…
Dinner will come naturally.
The Bottom Line
Some of the most successful couples I’ve introduced didn’t begin with candlelight dinners.
They began with a simple conversation.
Sometimes over coffee.
Sometimes over tea.
Sometimes at 3:00 on a Wednesday.
As a matchmaker who’s spent more than 16 years helping extraordinary people find love, here’s my official permission:
Go on the coffee date.
It might just change your life.
Frequently Asked Questions About Coffee Dates
Final Thought
The first date isn’t the relationship.
It’s simply the introduction.
Don’t let the format keep you from meeting someone extraordinary.
Sometimes the smallest invitation opens the biggest door.
About the Author
Erica Arrechea is the founder of Cinqe Matchmaking established in 2010. Cinqe works with successful singles across the US, providing introductions and concierge level matchmaking services for professionals seeking meaningful relationships. IG: @erica
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