Every Wednesday, I'm inviting you behind the scenes of my coaching practice. From My Coach's Chair is where I share real client stories (with details changed for privacy), the patterns I keep seeing, and the lessons I hope help you choose well. One of my clients once told me something I haven’t forgotten.
“I’ve accepted it’ll probably take 50 to 100 first dates before I find the right person.”
She wasn’t being pessimistic.
She was being practical—or at least, she thought she was.
She had recently come through a divorce after nearly two decades of marriage. She was rebuilding almost every part of her life at once. A new home. New routines. New finances. A future she hadn’t planned for.
Like so many women in that season, she’d also absorbed a familiar message:
“Dating after divorce is a mess.”
“There aren’t many good men left.”
“It’s going to take years.”
So she adjusted her expectations.
Not because anyone had shown her evidence.
Because she’d heard the story so many times, it felt true.
That conversation stayed with me.
Not because of the number.
Because of the assumption behind it.
She believed finding a healthy relationship was mostly a numbers game.
More dates.
More disappointment.
More endurance.
But what if that’s the wrong question?
What We Changed
Instead of asking,
“How many dates will it take?”
we asked a different question.
“How will you know when you’re sitting across from the right man?”
Those are very different problems.
One is about time.
The other is about discernment.
So we stopped trying to predict how long it would take.
Instead, we built a framework.
She learned to distinguish chemistry from character.
She stopped confusing intensity with emotional availability.
She paid less attention to how impressed she was...
...and more attention to how safe, respected, and emotionally settled she felt.
Most importantly, she stopped asking,
“How do I get the right man to choose me?”
She started asking,
“What evidence do I have that I should choose him?”
That single question changed the way she dated.
Four Dates Later
She met the man she’s now building a future with.
Was it because we found the perfect dating app?
No.
Was it because she suddenly became more attractive?
No.
Was it luck?
Maybe a little.
But luck doesn’t explain why she recognized qualities she might have overlooked six months earlier.
Consistency.
Kindness.
Emotional maturity.
The ability to repair after conflict.
A willingness to create clarity instead of confusion.
Those qualities had become visible because she finally knew what she was looking for.
The Lesson From My Chair
People often ask me how long it takes to meet the right person.
I honestly don’t know.
No coach can promise that.
But I do know this:
You can dramatically shorten the time you spend investing in the wrong people.
That’s the part we have influence over.
That’s why I believe the biggest breakthrough isn’t meeting the right man.
It’s recognizing him.
Because when you know what healthy love actually looks like—and you have a process for evaluating it—you stop spending months (or years) trying to turn potential into partnership.
You make better decisions sooner.
And that changes everything.
This Week’s Play
Here’s one journal prompt I’d love for you to sit with this week:
When you think about the last relationship that kept you stuck...
Were you making decisions based on hope...
...or evidence?
Write down three pieces of evidence you ignored.
Not to judge yourself.
Simply to begin strengthening one of the most important skills in dating:
Discernment.
Your Next Step
If this story resonated with you, I’d love to invite you to my free live training:
The Game Plan: How to Stop Wasting Years on the Wrong Men and Start Dating with Strategy
I’ll teach you the same three-part framework I use with my private clients—Clarity, Process, and Vetting—so you can stop relying on hope and start making confident, intentional decisions about the most important relationship of your life.