Listen to this article now

We all know entrepreneurs are sometimes regarded as some of the sneakiest beings on the planet, but everyone deserves love, do they not? And entrepreneurs are humans too. However, there really are some downsides when dating one—well, apart from always having a big dream that never seems to give them the time of day for their partners in the first place. When dating an entrepreneur, here are some red flags you should know and look out for.

All Talk

Entrepreneur couple sitting in silence after disagreement
Entrepreneur couple sitting in silence after disagreement

This has got to be the biggest red flag there is with entrepreneurs. So for all those looking to get into a relationship with an entrepreneur, I really do hope you are prepared for the frustration that comes with it. I mean, planning dates and always forgetting then apologizing with the promise to change. It is a talk that never sees the light of day once it is past their sweetened lips. Oh boy, are their lips sweetened! I mean, come on! All entrepreneurs are marketers and as such are great talkers. So where is the surprise when they stand you up for the thousandth time and give you the “It will never happen again and the “I will do better” talk. But doing better never actually happens. I tell you, it is one of those things that have you wanting to pull your hair out in frustration.


They say being an opportunist is a good thing, but is it really when you realize the person you are in a relationship with keeps trying to capitalize on your skills for their own selfish benefits, regardless of how you feel about it. In essence, dating an entrepreneur interprets to having your skills maxed out all in the name of being supportive. And, in most cases, getting emotionally blackmailed when you question their repetitive capitalization of your skills without clearly appreciating you or at least giving you some kind of acknowledgement or compensation for your maxed out skill use. But that is alright to them, though. For them, you are playing the perfect supportive partner. Need I scream red any louder?

Opportunist Part II

On today’s episode of a total red flag, we have the problem of being an opportunist once again, but this time with the friends you keep. You can’t ever have a normal conversation about that rich or well to do friend in peace anymore. In fact, you really cannot talk about any wealthy friend at all! All you would hear would be how to set up a meeting between your entrepreneur partner and the said friend. Don’t get me started on what will happen if you decline their request to meet your wealthy friend. All you would hear for as long as possible would be how you do not support or believe in them. Sheesh! The mental hassle of that!


Woman returning engagement ring to entrepreneur
Woman returning engagement ring to entrepreneur

Another red flag when dating an entrepreneur is having them ask for money. Now, this may not start immediately, and most times, it is more covert and not so pronounced. You hear talks about how they have one big idea or another sure to generate a lot of revenue. Then, they go on to talk about how they wish they could get an investor to entrust a small fee in their care. Now, these are the covert ones. However, there are those who would ask that you invest, talking about how you should support their dreams. Don’t get me wrong; you should support your partner’s dreams. However, it would be unwise to support foolishly or consistently support a dream with no realistic approach. By realistic approach I mean a plan. It is a terrible sense of entitlement; it should not be fed, nor should it be ignored. It is best to cut it off while it is just a sprout than to let it even bud.

Judgement Givers

This category of red flaggers is specifically for the entrepreneurs who hate to see others better than them. It is different when your partner tells you about people they had met and said other person’s business idea. But it is a different ballgame altogether when all they do is complain. Bitterly, I should add, about others they had met with business ideas. They would often even go as far as entirely trash talk the ideas of others because they had not thought of it first. This is a red flag and should not be ignored or brushed off. This should simply tell you how much they would trash talk you if you start doing better. They are egotistic and not in a good way because if they can say that about people they don’t know, who is to say they won’t say worse of you to your face all because they have no self-confidence. Or, to put it in plainer terms, because they suffer from a terrible case of low self-esteem as well as jealousy.

It’s Called Entrepreneurship, Not Gambling

Look, you need to understand that when your partner takes loans so frequently yet never pays back, it is something to worry about. Also, there is a pure and rather distinct difference between risk-taking and full-on gambling. Believe me when I say the line is thin. The line is so thin most times it gets blurred so severely. Here and know this clearly, risk-taking involves a definite plan and is different from gambling based on pure luck and more borrowing. This is when you will hear things like, “Babe, I promise this will be the last time.” But it won’t. They may hide it, but in the end, they will not be able to hide their addiction for so long, fully.

All in all, being in a relationship with an entrepreneur differs from one to the other, but you should look out for these tell-tale signs to avoid getting your heart broken or getting into a relationship of emotional abuse. Believe me, no matter how covert or how much you try to convince yourself it is the stress of the job, it will still bite you in the ass. Remember, red flags should never be ignored.

Do you know any other red flags when dating an entrepreneur? Let us know down in the comments.

This article originally published on GREY Journal.

Join the GREY Gang

Full of value, void of hype, tailored to your hustle, never pushy and always free.

  • 1. Practical Tips for Entrepreneurs
  • 2. A Pulse on Trends in the Startup World
  • 3. Pitch Your Business Get Media Coverage

Join the GREYGang