Your Dating Life Has a Leadership Problem
I spend a lot of time with successful people.
CEOs. Entrepreneurs. Doctors. Lawyers. Investors. People who run companies, manage teams, negotiate deals, make difficult decisions and build lives most people would consider pretty darn successful.
And then I watch how some of them date.
I’ve had a front-row seat for more than 30 years—33,000 first dates, 10,000-plus marriages and relationships, plenty of great love stories…and enough dating disasters to make me wonder how some very smart people ever made it past the first interview.
Because the same person who would never tolerate missed deadlines, vague answers, erratic performance or a complete lack of follow-through at work will tolerate all four from someone they met on Bumble because “the chemistry was incredible.”
Please.
Your dating life has a leadership problem.
And unfortunately, you’re the leader.
(QUIZ AT BOTTOM---Take it!)
You Would Never Run a Business This Way
Imagine you’re interviewing someone for a senior position.
Great résumé. Terrific first interview. Smart, charismatic and attractive. You can picture this person fitting beautifully into the organization.
Then they disappear for nine days.
They return with a breezy “Hey, stranger,” disappear again, cancel two meetings and announce that they’re “not really sure what they’re looking for.”
Would you hire them?
Of course not.
You wouldn’t even let them validate their parking.
Yet people do the dating equivalent every day. They keep investing time, energy and emotional bandwidth in someone who has demonstrated absolutely no ability to show up consistently.
Why?
Because the first date was exciting. Because the attraction was strong. Because the person looked fabulous on paper.
So did Enron.
That isn’t optimism.
It’s bad management.
Chemistry Is Not Due Diligence
Chemistry matters. I’m not going to pretend it doesn’t.
But chemistry is one piece of information. It is not the entire quarterly report—and it certainly isn’t permission to ignore an impressive collection of red flags.
You also need to evaluate consistency, emotional availability, communication, shared values—and whether this person’s life actually has room for a relationship.
Successful daters don’t make a major emotional investment based on one fabulous dinner. They watch what happens next.
Does the person follow through? Do their words and actions agree? Are they genuinely curious about you? Do they make actual plans—or simply send enough texts to remain technically alive?
That is dating due diligence.
And yes, it’s less intoxicating than planning your future wedding after two martinis.
It’s also considerably less expensive.
Stop Running the Same Failed Strategy
In business, when a strategy repeatedly fails, you change it.
You don’t continue pouring money into the same campaign because you’ve already spent money on it. You study the results, identify what isn’t working and adjust.
Dating should be no different.
If you’ve spent three years swiping without meeting anyone promising, more swiping probably isn’t the entire answer.
If you repeatedly choose emotionally unavailable people, the solution is not finding a taller, richer, better-looking emotionally unavailable person.
That’s not growth. That’s upgrading the packaging.
And if your requirements eliminate 98 percent of the dating population, it may be time to decide whether every item on that list is truly essential—or whether a few were added after a particularly unpleasant glass of Chardonnay.
Thomas Edison said:
“Our greatest weakness lies in giving up. The most certain way to succeed is always to try one more time.”
I agree.
But “try one more time” doesn’t mean repeating the same behavior and waiting for the universe to reward your commitment to poor decision-making.
It means trying again with better information, a smarter strategy and the courage to do something differently.
Conduct Your Own Performance Review (Take the Quiz below and send it back to me today!)
If I were sitting on the board of directors of your dating life, here’s what I’d want to know:
What have you actually done in the past 30 days to meet someone?
How many conversations have you started?
How many invitations have you accepted?
Where have you gone besides your usual places?
Have you asked anyone to introduce you?
Have you updated your profile—or are you still using photos from 2019 because they’re “basically accurate”?
And most importantly: Are you behaving like someone who genuinely wants a relationship, or like someone who simply enjoys discussing the lack of one over brunch?
There’s a difference.
Wanting love is an emotion.
Creating a dating life that can produce love requires action.
Enough waiting. Enough overthinking. And definitely enough dating the same person in a different outfit.
Your dating life doesn’t need another motivational speech.
It needs leadership.
So call the meeting. Review the results. Fire the strategies that aren’t working. And, for heaven’s sake, stop promoting people who haven’t even shown up for the job.
Ready to shake things up? Reply to this email with “I’m ready,” and let’s book your private Dating Strategy Session.
And, take the quiz and send it back to me…I’d love to read where you are at!
We’ll figure out what isn’t working—and fix it.
xx, Andrea
Click the file link below to download this self-check.
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