How to Start Dating an Entrepreneur


Anyone who has ever dated, been involved with or married to an entrepreneur knows only too well how different their way of thinking is from most people. This difference can be challenging for the entrepreneur’s partner, especially if he or she hasn’t yet accepted the fact that their partner thinks and does things in a different way.

So if you’re dating or thinking about dating an entrepreneur, it would be a good idea to check first if he or she really is self-employed and not just blowing hot air. Knowing how to communicate with your entrepreneur girlfriend or boyfriend and how to adapt to their lifestyle can give you a pretty good idea on whether or not you can handle the relationship. There are no hard and fast rules to dating an entrepreneur, but the following tips can help.

  1. Check if you’re really going out with an entrepreneur. People who have their own business have certain traits that are typical to this personality. Of course, there are instances when this might not hold true. For instance, a business owner who’s just making it big might be advertising his success by loading on the bling or an old-timer might suddenly opt for retirement. But upon careful scrutiny, you’ll find that they exhibit some of these traits.
  • They’re very cautious about money. Don’t be surprised when your entrepreneur date picks you up in a solid and practical car or you have dinner at a nice but moderately priced restaurant. People running successful businesses are always thinking of the bottom line and are always calculating the costs. This might lead to unexpected low blows during fights when they might chide you over how much money they’ve already spent on you.
  • They’re very conscious about their time. Entrepreneurs have a thousand things to do and only a few hours a day to do it so they want to squeeze everything they can in 24 hours. Check their offices and you’ll probably see a comfortable couch for them to take short naps in. Don’t be surprised if they make calls or check their emails while having lunch or dinner. They might also complain if they see you doing something that they think of as a waste of time. Obviously, this would lead to arguments about how they divide their time between their relationships and work. However, if you can come to a compromise with your partner, then everyone will be a winner.
  • Entrepreneurs love taking risks. Some might think that entrepreneurs are wary about taking risks, but they’re not. After all, they wouldn’t have launched their own businesses if they were afraid of risks. But that doesn’t mean they’ll just jump in. You can bet that whatever risks they take have already been analyzed and deliberated on. Entrepreneurs are also a competitive bunch and they’ll probably be spending whatever free time they give themselves playing sports or games.
  • Most entrepreneurs are loners. They can socialize with the best of them, especially when they’re networking. But don’t expect them to be heading out to the nearest rave party once they reached home to relax. These are people who don’t follow the herd. They won’t succumb to what the rest of the world thinks. Instead, they will do the opposite or will read between the lines and figure out what will happen in the future.
  • They love solving problems. They are born problem solvers and won’t be satisfied with just talking through a problem. They will insist on coming up with a solution. They might even try to solve your problems for you, which would ultimately lead to some big problems. If you want them to stop solving your problems, then you have to be direct in telling them so. While they might not take it kindly, they’ll eventually agree with you once they see that you can handle your own problems.
  • Entrepreneurs are very direct and honest. They don’t have the time or the inclination to bandy words so they will tell you what they want or think. They also have a strong sense of commitment and most can be trusted to uphold agreements.
  1. If you want to make your relationship work, then learn to take risks. If you’re one of those who shrivel in fear at the face of risks but are dating an entrepreneur, you only have two choices – learn to get over your fear of taking risks or learn to back up someone who loves taking risks. Remember that entrepreneurs won’t be successful if they don’t take risks or are scared of taking them. Cultivating a more accepting or zen-like attitude towards the ebb and flow of life will help you when you’re in a relationship with a business-minded individual.
  2. Continue cultivating your independence and keep yourself busy with your own thing. If you’re one of those high-maintenance girlfriends who need a lot of attention, then you’re going to have a problem if you’re involved with an entrepreneur. These are people who will spend a lot of time in their office, in meetings, on the phone or in front of the computer. Women who have their own life and activities usually fare better in relationships with entrepreneurs.
  3. Spend money well and show that you understand money’s worth. And when we say worth, we’re not saying you know how much something costs. But when you’re involved with an entrepreneur, don’t expect them to just blow their money on anything. Entrepreneurs appreciate the value of money and tend to spend it on worthwhile or well made things.
  4. Cultivate a positive and optimistic personality. Your entrepreneur honey will love you all the more for it.
  5. Learn to adjust your time and plans. As you might guess, most entrepreneurs are workaholics and are driven to work long hours and days. So if you’re planning on being involved with an entrepreneur, don’t be surprised if he still does a little bit of work even during your dates or vacations. You should also get used to the fact that some of your dates would involve activities that would push his or her business further.
  6. Learn to distinguish when they’re on work mode and when they’re not. This isn’t hard to figure out. If your sweetie seems distracted, gives one word answers or irritable when you interrupt him, then he might be working on a project or thinking of a solution. Of course, things are different and better once they’ve turned their work mode off. Contrary to the perception that entrepreneurs are these moody, nerdy and serious people, most are actually very charming, smart and funny. Most of the time, this charming personality is often just seen by their friends, family and loved ones.
  7. But if your partner is on work mode, it would be a good idea to be practical and direct if you do need to talk to him or her. They don’t really have the time or patience for long winded requests or discussions during this time, so going straight to the point with your request or with what you want to say will save everyone unnecessary aggravation. So instead of telling a story about this problem with the sink and wanting to hire a plumber that’s a friend of someone you met at a party that you went to last month with him during one of his business trips yadda yadda yadda, just tell your partner that you need to hire a plumber who should come ASAP to fix the sink. See, sweet and simple.
  8. We have to acknowledge that at some point, you will have problems talking to your partner about something that’s of vital importance to you. It might be about how he or she manages his time or about your need for more of his time. When this happens, it would be better that you talk to your partner in a direct and business-like manner. This might sound and feel weird since you’re talking about your relationship but believe me, your entrepreneur will understand things better if you break down your points and analysis in this manner since they can relate to this type of communication better. So instead of whining and nagging about how much he’s on his Blackberry closing deals instead of spending time with you or paying you more attention, call his attention with a simple and direct statement. Give your inputs, your analysis and your demands. Instead of shouting out your ultimatum, discuss things like it’s a business negotiation.
  9. Work out a good balance that both of you will be happy with and demand that it’s followed. This is probably the biggest problem that newly successful entrepreneurs would face. The more experienced ones already know or have already learned that it’s important that there’s a balance in their lives or they’ll just burn out. But new entrepreneurs seem to think that they need to get everything done now and believe that once they achieve what they want, their life and partner would still be there waiting. If you truly want to make your relationship with an entrepreneur work out, then come up with a plan and treat it like a business proposal. Negotiate all the terms that are important to you and come to a decision on what to expect with regards to the ROI (return of investment).
  10. Never forget that your entrepreneur truly cares for you. They might seem heartless at times and oblivious to your needs, but they wouldn’t have pursued you if you weren’t important to them. They’re just like new mothers whose whole life and attention is focused on her newborn, but it doesn’t mean that they have forgotten you or they have totally changed into an empty shell that just lives for business. Bear in mind that their time is the biggest thing they can sacrifice for you. So when they’re giving you their time and attention, it should tell you how much they care for you and how high you are in their list of priorities.


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