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How to Date an Entrepreneur Woman

How to Date an Entrepreneur Woman

How to Date an Entrepreneur Woman

Every woman on the face of the planet has been asked, “what’s your favorite position?”

Many might take the opportunity to educate the barbarian mind of a man as to what sexual position women enjoy most.

Not Lauren Conrad.

When asked this question on Sirius XM’s show, Sway In The Morning, she responded brilliantly by saying that her favorite position is quote, “CEO.”

You can see Sway’s face in the clip below pause for a moment as he combs through his sexual position library looking for the position of CEO. After a moment he rejoices in Conrad’s brilliance.

This is what it’s like to date a woman entrepreneur.

When you date an entrepreneur you’re dating a woman whose mind is constantly revolving around her work. Forever tinkering with ideas and dreaming big.

Like Conrad, she might not have time for cheap jokes and casual sexist chit-chat — she’s too busy being a boss.


How To Date An Entrepreneur Woman

In this article, we’ll talk about how to date an entrepreneur.

I’ll tell you why dating an entrepreneur woman is awesome, how their behavior differs from other women, and what dating them will look like.


Dating a female entrepreneur is kinda like dating a single mom with kids, except her work is her baby.

As you might expect, children always come first.

A mother has carried her child around inside of her for nine months.

When they’re born she breastfeeds them, entertains them, feeds them, sings them to sleep, wakes up 37 times a night to put them back to bad, and does like a billion other things to make sure they’re safe, happy, and don’t have crap all over them.

She feels the same sense of ownership that she does over a baby, over her company.

That means that you shouldn’t be surprised when she suddenly cancels on your upcoming date or is preoccupied when you two are at the movies.

The woman is busy.

how to date an entrepreneur woman

A new entrepreneur may work 80+ hours a week.

She may only work 20 hours a week on her new venture, all while maintaining her 9-5.

The point is that her work comes first.

Accept that her dream isn’t to have prince charming sweep her off her feet. She doesn’t want to be swept off her feet — she needs those feet to go places.

In reality, her dream is to build whatever company she founded, finding love might be secondary.

My advice would be to acknowledge how important her work is and to give her space when she needs it.

She’s much more likely to keep you around if you don’t complain that she never has time to work out.

The woman’s already stressed out.

The last thing she needs is another thing to worry about.

She Likely Won’t Work 9-5 pm

How do you date a woman that never has time to date?

It’s a quagmire but one you’ll have to navigate if you want to land a boss-ass woman.

Here’s how you can still date a woman that has little to no time to date.

1) Make Dating Seamless

Ask a woman who’s worked her ass off all day to a dance class 45 minutes away from where she works on a Tuesday night and see what she says.

Or rather, don’t.

She’ll say no. Literally just no.

If she doesn’t have time to snub you in a full sentence she certainly doesn’t have time to drive out of her way and expend energy she doesn’t have.

To guarantee that she accepts your date requests make them super easy for her to accept.

That means making them:

— Close to her work or home

— Brief, 1-2 hours in length

— Dates that take place during lunch or just after work

— Chill dates that won’t require her taking a shot of espresso just to get through it

2) Plan Dates In Advance

Even work-centric entrepreneurs need some time to relax.

Instead of prodding her last minute to hang, ask her days in advance so she can carve out time on her calendar.

Or better yet, ask when she’s free so that you aren’t asking her to choose between you and work.

If you do plan a date in advance make sure it’s a fun one. An entrepreneurial woman won’t be impressed by a basic coffee date.

Here are some date ideas that might impress her:

— Axe throwing

— Hit up a comedy club

— Go to a sporting event

— Hit up a vineyard or go to a wine tasting

Drink wine and paint

3) Use A TDL

TDL stands for time, date, location.

If you ask an entrepreneur, “Hey, wanna go out sometime,” she’s probably going to say no.

And if you’re then waiting for her to ask you out, you’ll be waiting until her company’s out of the red.

Again, make things easy for her by giving her a concrete date time, date, and location so that she can either accept or decline.

She’s Likely an Alpha and Knows What She Wants

Bosses aren’t used to taking orders.

Though, it’s true that sometimes being in control of all things at work can make a person want to be super beta in their personal lives. But just know, when it comes to her day-to-day, she’s in charge.

She might appreciate you planning compelling dates because she’s likely too slammed to do so herself (plus, generally speaking, women don’t love being the planners) but for an alpha boss lady, she may have trouble releasing control and suggest something other than what you had planned.

It might be helpful to ask questions about the types of dynamics she likes.

Ex: If she’s the boss in the boardroom, does she also want to be the captain in the bedroom?

These types of questions will show her that you understand a thing or two about what her life is like and she’ll appreciate your perceptiveness.

The more you know about her and how she operates the more likely you are to woo her.

Ask questions, show interest, and genuinely give a crap about the words coming out of her mouth.

This isn’t advice unique to dating an entrepreneur woman but is what every single man should do when looking to court a woman.

They’ll Be Emotional Highs and Lows

Running your own business is a non-stop roller coaster.

Dating someone that can’t get off this ride means that in order to keep up you too have to buy the ticket and hop on.

It ain’t easy running your own business or pursuing your dream. Trust me, I’ve been building this site for almost a decade.

It’s high-risk, high reward and there will be times when things don’t go her way. If she’s an entrepreneur, she likely lives for the thrill of it often, which means life can be a bit of a rollercoaster.

But the upside… my God the upside.

She’ll carry her feels around with her. She won’t clock out when she goes home or meets you at that Italian restaurant.

If she had a good time so will you.

She’ll ride those positive and negative emotions and let them shape her every interaction.

So yeah, there will be highs and lows.

Just remember to not throw up on your date if you get motion sickness.

She Might Check Her Phone on Vacation

We’re addressing this one because it’s one of the most common pet peeves, right next to loud chewing, arriving late, and people that claim that they “don’t see color.”

how to date an entrepreneur woman

Checking one’s phone on a date is a massive pet peeve.

But Stacey from Tinder checking her IG while on a date and Beth the entrepreneur from Hinge checking her email to see if she scored a new investor are two different things — and as such deserve two different responses.

Look you’re going to have to make some concessions when dating a female entrepreneur.

Show that you understand by acknowledging that her work comes first and not get annoyed.

Show her that you can hang by not becoming peeved every time she checks her device.

She’ll Be Much More Passionate Than Other Women You’ve Dated

Who do you want to date more?

The chronic Netflix binger or the woman that just created an app that helps you not only block but spam, spam callers.

One woman wakes up every day with a clear goal in mind and a purpose in life.

She is hungry, eager to try new things, and radiates energy.

When you date a woman like this, you too will start to feel that energy.

Her thirst will become your thirst.

Look, the majority of people are boring.

Instead of dating someone in the majority, why not date the woman that every woman wants to be?

She’ll Push You Past Your Comfort Zone

Maybe you don’t even like roller coasters. It doesn’t matter.

When you’re with her, you’ll constantly be pushing your comfort boundaries.

It’s easy to push yourself on a daily basis when the person you’re spending all your time with is doing the same.

She will be your model.

Entrepreneurs are risk-takers, they’re not afraid to do things that scare them in order to get what they want. They don’t tend to understand the idea of playing life safe. This means she probably won’t put up with the status quo.

If she hears you say there’s something on your bucket list you haven’t done, she’ll push you to do it.

This can cause friction if you like things predictable and certain. But it can also make life rich with meaning and fulfillment. 

Time To Start Your New Love Venture

Every great new venture starts with investment.

Investment of time, passion, and money.

Are you seriously ready to date a badass entrepreneur woman?

Do you have the skills to woo a highly intelligent and beautiful woman?

If you do, great, go forth and prosper.

If you don’t, well, I have some advice.

To learn what I have in mind let’s talk via a 1-on-1 Zoom call with me or one of my colleagues today.

Tell me what your goals are and I’ll tell you how you can attain them. And at the end of our session we’ll discuss my private coaching, personal matchmaking, and self study programs to see if they’re a fit for you.

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