There was a time when dating advice for successful women sounded remarkably like instructions for becoming less successful.
Don’t talk too much about your career. Don’t appear too interested. Don’t call first. Don’t suggest the date. Don’t pay. Don’t be too opinionated. Don’t be intimidating.
And whatever you do, don’t let your date know just how accomplished you are.
Apparently, you could run a company on Monday but by Saturday night you were expected to become mysteriously incapable of choosing a restaurant.
No, thank you.
Some dating advice has changed. Some hasn’t. And social media has introduced an entirely new universe of rules about texting intervals, “energy,” who should pursue whom and how quickly you’re allowed to reveal that you actually like someone.
But there’s a better starting point for accomplished women:
A healthy relationship shouldn’t require you to audition as a smaller version of yourself.
Here are seven dating rules you have permission to stop following.
1. Don’t Talk About Your Accomplishments
Let’s start here.
Your career isn’t your entire identity.
But it is part of your life.
If you’re proud of something you’ve built, earned, created or accomplished, you don’t need to hide it to protect another person’s ego.
Talk about the promotion. The business you started. The degree you earned. The project you’re excited about. The risk you took.
Then ask about what excites the person across the table.
There’s a difference between sharing what matters to you and turning dinner into your annual performance review.
The goal isn’t to impress.
It’s to let someone know you.
And if your success genuinely makes another person uncomfortable?
That’s useful information.
2. Don’t Show Too Much Interest
Remember the old advice to play hard to get?
Wait before returning the call. Don’t appear too available. Make the other person wonder whether you care.
Many women have reached a stage of life where that sounds less like romance and more like administrative overhead.
If you’re interested, you can show interest.
Send the text. Say you had a wonderful time. Suggest seeing each other again. Give the compliment. Ask the question.
There is vulnerability in letting someone know you like them.
But vulnerability and desperation aren’t the same thing.
Being interested isn’t embarrassing.
What’s more revealing is whether that interest is reciprocated.
3. Don’t Make the First Move
You negotiate contracts. Lead meetings. Ask for raises. Pitch ideas. Start companies. Introduce yourself to strangers at networking events.
But when you meet someone interesting, you’re suddenly supposed to wait?
You don’t have to.
Ask someone to coffee. Suggest dinner. Send the first message. Propose the next date.
Initiative is not a masculine characteristic.
It’s initiative.
And making the first move doesn’t mean you’re committing to a relationship. You’re simply opening a door.
The other person still gets to decide whether to walk through it.
4. Let the Other Person Make All the Plans
There can be something wonderful about someone saying:
“I’ve got this. Be ready at seven.”
But there’s an equally important distinction between being cared for and becoming passive.
If you know about a restaurant you’d love to try, say so. If there’s a concert you want to see, suggest it. If you’d rather hike than sit through another two-hour dinner interview, speak up.
Dating is partly about discovering how two people’s lives fit together.
That becomes difficult if only one person’s preferences are visible.
You don’t need to orchestrate every date simply because you’re good at organizing things, either.
Let someone else contribute.
The goal isn’t control. It’s reciprocity.
5. There Doesn’t Have to Be a Rule About the Check
Few dating subjects generate more rules than the check.
He should pay. The person who invited should pay. Always split it. Never split it. Offer once but secretly hope they refuse.
We could make this much easier.
Be generous.
Be gracious.
And communicate.
Different people bring different expectations, cultures, financial circumstances and ideas about dating to the table.
If someone invites you and wants to treat, you can accept. If you’d like to reciprocate next time, do it. If splitting expenses feels right, do that.
As relationships develop, money becomes far more important than who paid for the first dinner anyway.
You’ll eventually want to understand how someone thinks about spending, saving, generosity, debt, lifestyle and financial responsibility.
Compatibility around money matters more than performing the “correct” move when the check arrives.
6. Don’t Be Intimidating
This one needs to go.
A woman should certainly care about how she makes other people feel.
We all should.
But there’s a difference between being arrogant and simply being accomplished.
Don’t apologize for your education. Don’t minimize your title. Don’t pretend your work doesn’t matter to you. Don’t make your ambition adorable so it seems less threatening.
And don’t automatically assume that someone’s lack of interest means you were “too much.”
Sometimes two people simply aren’t a match.
That isn’t failure.
That’s dating doing its job.
The question isn’t:
How can I make myself less intimidating?
Try:
Can I be fully myself around this person, and does this person seem comfortable being fully themselves around me?
That’s much more useful.
7. Don’t Bring Your Work Self Into Dating
This one requires nuance.
Some of the qualities that helped you succeed professionally may serve you beautifully in relationships: confidence, curiosity, communication, resilience, reliability, knowing what you want and being willing to have difficult conversations.
Others may need to stay at the office.
You don’t need to optimize the relationship. You don’t need a five-year strategic plan after date three. Your date isn’t a candidate you’re interviewing. And another person’s emotions aren’t a problem for you to solve.
Successful women are often rewarded professionally for being decisive and capable.
Relationships sometimes ask for something different:
Uncertainty.
Listening. Patience. Vulnerability. Letting another person contribute. Allowing something to unfold without knowing exactly where it’s going.
The answer isn’t to become less powerful.
It’s to expand your definition of power.
Don’t Confuse Standards With a Checklist
Knowing what you want is healthy.
But occasionally the picture becomes so specific that nobody can get through the door.
Certain standards should be nonnegotiable: kindness, respect, honesty, emotional safety and the shared values that matter to you.
But height? Job title? Zip code? Exact educational background? Whether someone checks every box on the first date?
Perhaps not.
Ask yourself:
Am I protecting an important value, or protecting a preference?
They’re not always the same thing.
And Please Stop Treating Dating Like a Hiring Process
Accomplished women know how to evaluate.
We analyze. Compare. Assess. Notice.
It’s useful professionally.
On a date, it can become exhausting.
Instead of spending the entire evening asking:
Does this person meet my criteria?
occasionally ask:
How do I feel when I’m with this person?
Am I curious? Do I laugh? Do I feel respected? Can I relax? Do I like who I am around them? Do I want to know more?
Compatibility isn’t always something you can capture in a spreadsheet.
The Best Dating Rule May Be No Performance at All
There is no shortage of advice telling women how to become more desirable.
Be confident, but not intimidating. Independent, but let yourself be pursued. Successful, but not too focused on work. Interested, but not too interested. Sexy, but not trying too hard. Available, but definitely busy.
It’s exhausting.
And perhaps we’re asking the wrong question.
Instead of:
“How do I get this person to like me?”
try:
“Do we like each other as we actually are?”
That’s a very different kind of date.
Pink POV
Your career success doesn’t disqualify you from intimacy.
Your ambition doesn’t need an apology. Your intelligence doesn’t need disguising. Your directness doesn’t automatically need softening.
And you don’t have to pretend not to want something in order to be worthy of receiving it.
Bring the woman who leads the meeting.
Bring the woman who doesn’t always know the answer.
Bring the ambitious one. The funny one. The nervous one. The independent one who still wants someone to lean on occasionally.
Bring the whole person.
Because the goal isn’t to become the woman someone else has been taught to want.
It’s to find a relationship in which neither of you has to become smaller to make room for the other.
