How To Date An Entrepreneur

As a self-employed single person, I’d like to share with you 9-to 5-ers a little inside scoop on how to date an entrepreneur. There are many pros and cons, but ultimately, it’s up to you to decide if their individual lifestyle and personality jives with your own.

Here are my top 5 warnings—ahem, tips—on how to date an entrepreneur:

1. Be flexible with your schedule.

Entrepreneurs don’t typically have an excess of free time, so making time for dating can be a challenge. This means you’ll have to be a bit flexible about when and where you spend time together. Get ready for non-traditional dates! Think breakfast dates, weekend-long excursions (the silver lining to making our own schedules), and lunch dates via FaceTime. When considering how to date an entrepreneur, ask yourself whether or not you’re willing to date around his/her busy schedule. Will you feel disappointed or unappreciated if he doesn’t take you out for the traditional dinner and a movie? Or on the flip side, will you feel rejected if she hardly ever is able to accept your invitations for evening or weekend dates?

Personally, quality time is my top love language. When I’m dating someone, I’m trying to squeeze in quality time together at every possible opportunity. For example, I might invite him to drive along with me as I do some of my marketing visits, or invite him to work out or walk my dogs with me. There are many possibilities so long as you’re comfortable sharing the “small stuff” with someone. Keep in mind that while quality time is my love language, this is not true for all entrepreneurs.

2. Ask questions about their approach to business and finances.

Many entrepreneurs manage resources, including money, extremely well. But just like the rest of the human race, entrepreneurs vary greatly in their belief systems about money, and in their ability to manage money. Overall, it is important to recognize that entrepreneurs are risk-takers—some more than others.

Not every entrepreneur is smart about how they take risks to pursue a new idea, so when dating an entrepreneur, it is wise to ask a lot of questions about their approach to business-building. To get a good feel for their journey, ask about their past business adventures, and ask about ideas for the future. Are they looking to remain in the line of work they’re in now, or are they yearning to move on? Is there a big idea that they’ve been waiting to pursue? Ask how this approach may shift once he/she is married. Do they intend to include their spouse in this decision-making? Find out what drives them. Is God involved in their business planning? Do they seek His will for their business?

These kinds of questions will help you gauge how much his/her entrepreneurial pursuits could impact your future life together. Questions about business and money are very personal, but discussing financial compatibility early on in a relationship is typically regarded as good all-around dating advice. Dating an entrepreneur is no exception.

3. Flexibility and a sense of adventure are a must.

“I wonder…” is the mantra of an entrepreneur. We are constantly dreaming of what could be! Many people are entertained by the entrepreneur’s eternal think tank of a brain, but this mindset has also been known to annoy a practical, grounded mind. The constant shift of ideas, lifestyle, hobbies, interests and topics of conversation is unnerving to certain personalities. If this gives you pause, you’d be wise to seriously consider this early on in your relationship with an entrepreneur. It’s not going away anytime soon.

As for how to date an entrepreneur, feel free to get creative! Since most of us are the adventurous type, we appreciate a random, off-the-wall activity, outing or event. This takes away some of the pressure in planning dates with your entrepreneur. Most of us welcome creativity, so the possibilities are virtually endless.

4. Practice listening.

When you first get to know someone, it’s normal to talk in-depth about your career. You should know up front that when you’re dating an entrepreneur, this tendency to talk about work will not fade with time! It may often feel like you’re dating the person and his/her business. If you’re not interested in learning all about it, you may as well move on now.

I have never met an entrepreneur who is not endlessly brainstorming. While they always have a new idea, not all ideas are good ideas. If you emerge as your entrepreneur’s preferred sounding board, it will be your job to walk the fine line between encouraging the thought process and talking us off the ledge of a bad idea. This is a tough line, but with a little love and a lot of patience, you’ll be just fine.

5. Make peace with interruptions.

Interruptions are inevitable when dating an entrepreneur. As the creator and owner (and sometimes also the manager and operator) of a business, an entrepreneur is never really “off.” Things will always come up that need to be attended to in a timely manner. The most seasoned entrepreneurs know how to balance their priorities, but this is a learning process—your entrepreneur may not be there yet.

How do you date an entrepreneur who can’t put their relationship first? As they work through the process of finding balance, you, their partner, will need to be reasonably patient. It’s a tough balance to find, and it may be a work in progress for a while. Ask yourself if you’re okay with this, and at the same time, do make sure the entrepreneur you’re dating is actually striving to find this balance and isn’t just paying it lip service. Balance is mandatory in a long-term relationship.

At the end of the day, entrepreneurs are rarely boring! If you like to shake things up, you’ll love dating an entrepreneur; but if you prefer the status quo, entrepreneurs may be a challenge for you. Most importantly, entrepreneurs are typically creative, passionate people. When we’re “all in” on an idea (or a person), we pour out our entire heart and soul. If you win the heart of an entrepreneur, I don’t think you’ll be disappointed.