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Professional Dating

Entrepreneur Dating: Chat and Meet Innovative, Creative, and Driven Singles 

Last updated on 2 April 2024

     It is well known that being an entrepreneur is not all sunshine, rainbows, and money. It can be a very difficult road to take as it will take up a lot of your time, whether in the early stages or once you have established yourself! Many people do not realize what it takes to be an entrepreneur, let alone a successful one. You could argue that it quite literally takes one to know one in this situation. 

Entrepreneurship is not limited to one area. With the enhancements in modern technology, there are entrepreneurs in every industry you can imagine, and some you possibly cannot! Due to their dedication to their work, and developing their particular business/career, they often find dating or searching for love difficult, especially face-to-face. Therefore, as you are probably aware, many entrepreneurs enter into the online world to find love. It is easier for them to do as it can be done on the move, when and where it is easier for them, and can connect them to people that are very similar to themselves. In short, online dating is far more accessible than trying to meet people in the ‘real’ world. Many entrepreneurs look to make romantic connections with other entrepreneurs as they will often have similar personality traits and will understand what it takes to be an entrepreneur. If you, the lovely entrepreneur reading this, feel that it would be better to date someone from another profession you may be right. You would have different worries, different things to talk about, and a different story altogether. However, this could make life for you both quite frustrating if they do not understand your working hours, dedication, etc Therefore, we think that it would be better for you to establish a connection with another entrepreneur. Here we look at the positives of dating another entrepreneur:

  • The first positive is that they may have the same professional background/ journey as you. Meeting people from different backgrounds, including their career, is not a negative but dating someone with the same, or similar, career to you definitely has its bonuses. The first of these bonuses is that both of you will be able to relate to the other when the topic of work comes up. While your respective businesses might differ you will possibly have the same journey or desire to become successful. You can start a romantic journey while learning from each other about your businesses. 
  • As previously mentioned, another entrepreneur will understand what it takes to run your own business. Many people think it is easy to be a successful entrepreneur and run your own business. However, to be a successful entrepreneur you need to put in the work and that can involve long hours, working weekends, and spending time away from your social life. Dating another entrepreneur means they will understand that you may not always be available or that you will be available and different times. Dating someone else may be difficult as they may not be as understanding! 
  • You could argue that all entrepreneurs have very similar personality traits. Some of those traits are dedication, resilience, quick thinking, attention to detail, and hard work. Entrepreneurs will look for people with similar traits which, primarily, will be other entrepreneurs. Now, this does not mean that every entrepreneur will be the perfect partner but you will enter into a relationship with another like-minded person knowing that they, should, have most, if not all, of these traits!

Many people would argue that dating someone with a completely different career to you has far more potential for success. However, it is probably more likely that dating someone from the same professional background as you provide you with more chances of romantic success. This is because you will immediately have something in common!

Tips and Advice for Online Messaging or Other Interaction in Interpreneur's Chat

     You may think that because you and your prospective date are both entrepreneurs you know exactly what to talk about and the topics you may need to avoid. However, this is not necessarily true. There are in fact questions that you should not ask (at least in the beginning) and topics that you should avoid (again, especially in the beginning). Just because you share your area of work does not mean that the conversation will come naturally easy.  The first reason for this is that while you both might be entrepreneurs your businesses could differ greatly! First, we are going to look at the questions and topics to avoid.

  • You do not want to delve too deep into their personal life. This could be said when dating anyone. Information about their financial situation and/ or relationship history should only be shared when each person is ready and a connection based on mutual trust has been well established. Do not ask questions such as ‘How much does your business make annually?’, ‘Why are you still single?’, ‘why did your previous relationships not work out?’ etc as you are likely to put your new friend off rather than encourage a relationship.  You should only discuss past relationships if they bring it up (their own previous relationships) and are happy to discuss it.
  • Do not focus too much on work. While we suggest that you discuss your respective careers this should not be the sole focus of your discussions. It is always good to discuss your respective journeys and the particular businesses you both own/ manage. However, you want to get to know the person, not just their profession, so make sure you discuss more than just work!! This can be difficult for entrepreneurs to do as their business is usually their life. Step away from this and make sure to get to know the person and allow them to get to know you. 
  • Only share aspects of your business you would be happy to share with anyone. You should keep some things to yourself, a bit like being confidential in other businesses. Share parts of your business you are happy to share with a complete stranger and keep the finer details to yourself….at least until a more secure, romantic connection is made!

You need to avoid being boring! Avoid talking about the weather or yourself all the time. You want to keep them interested in you and not get bored with your talking about the same topics, yourself or your business all of the time!

Now, the most important things to remember are the topics you should discuss and the questions that are a definite must to ask! Here, we are going to look at the topics and questions that are definitely appropriate when dating another entrepreneur, whether you are talking face-to-face or online.

  • Being the boss of your own business probably means you have both spent the day making sure any staff you have are okay and the business is running smoothly. It is possible that neither of you has been asked how you are doing or how the day is going. Ask how they are or how their day has gone. This shows you care about their well-being and are genuinely interested in them. If they ask you the same you can take this as them caring about how you are and showing genuine interest in you. 
  • Make sure to move away from talking about your businesses and find out about the other person. Ask them about their hobbies and discuss your own. Talk about other aspects of their life such as the food they enjoy, what they do for fun, and how they like to relax. 
  • It is always good to find out about your dates journey. We do not mean that you should pry into their dating history or find out every private piece of information. You could ask about their professional journey and see if there are any similarities! You could discuss when and how you created your respective businesses, why you became an entrepreneur, and what your long-term goals are. This will show your interest in the ‘whole them’, not just their social or career side. 
  • It is likely that your prospective date would much rather talk about something other than their business to establish a life away from work. You could talk about memories from your childhood, ask them about their family, or discuss your hobbies. Not only is this a wonderful way of getting to know each other but also works wonders as a back-and-forth conversation. You can discuss the similarities and differences between you both (for all of the aforementioned topics), share comical stories from the past, and see how your families compare. One piece of advice here though. When discussing families make sure you do not ask too deep a question. 
  • If you have started your dating journey with your date online then we hope that you will have taken the time to read their profile. This is the best thing you can do to make a fantastic impression. If you comment on what they write or ask questions relating to their profile it will show you have taken the time to find out more about them before engaging them in conversation. Entrepreneurs pay attention to detail at all times and want to learn as much as possible and will appreciate someone else who does the same!
  • This next one could be said of dating anyone, no matter their profession. Ask general, open-ended questions. Try not to ask closed questions (those that seek a yes or no answer). You want to make sure the conversation flows at all times. You could discuss a whole host of topics such as films, cooking, music, travel, etc. Just make sure that the topics you pick are of interest to you both! If you do all of the talking they will get bored very quickly!

Whether you have been an entrepreneur for a long time, with a well-established business or you are just starting out you must make sure to treat each other with respect. Too often you find well-established entrepreneurs look down on or talk down to upcoming entrepreneurs or those new to the business who feel they know more than the ‘old school’. Treat each other with respect at all times, you are both trying to achieve the same goal! 

Date Ideas for Single Enterpreneurs!

     You may either start your entrepreneur dating journey in the offline world or move there from the online world. Either way, you will want to make sure your dates are enjoyable for both parties involved and that you plan dates that help take you from friends to a romantic couple. Depending on the types of businesses you both own, you may work long/ different hours which can make dating difficult. However, the below date ideas should be accessible for all!

  1. Plan your weekends/ free time accordingly. This could be the only spare time you have and you do not want to waste (all of) it watching television. You could plan to head off to street festivals, food events, or live music. You need to make sure that you both plan your dates with each other in mind. You want your time together to be time well spent, not time wasted with one of you wishing for a different activity!
  2. If you have been stuck inside all week, running your business, you will probably want to head outdoors and get some fresh air!! Why not head out for a picnic together? You will both benefit from some fresh air, good food, and some wonderful company as well as seeing some natural sunlight!
  3. Who doesn’t enjoy a classic date? You could take your date out for a romantic meal, head for a coffee date, or just go for a romantic walk. As the old saying goes, if ain't broke why fix it? Just make sure you pick a date that gives you both the opportunity to talk and get to know each other. The old classic of going to the ‘pictures’ (cinema) is not really viable as you will not have the chance to actually speak with each other. You do not want to spend up to two hours in silence, staring at a screen!
  4. A themed dinner date is another fantastic date idea. This is where you pick a particular cuisine and run with it! You pick a cuisine that you both like and either cook that meal together or order it in! Open a bottle of wine, eat some delicious food, and spend some quality time together!
  5. If you have dated for a little while, you can start introducing new date ideas. Some of this will be dependent on your interests. You could get a nice bottle of wine, turn off the television, turn on some music, and have a cheese and wine night. One fun game that a lot of people do, is the date night choosing game. People play rock, paper, scissors. Whoever wins each round picks something different for the night, for example, the first winner picks the starter, the second the main, the third the desserts, the fourth the drinks, etc. You could do the same to pick your activity. Not only is this fun, and different every time, but it provides you with a wonderful evening!
  6. While you are both entrepreneurs you may well want to move away from this completely on your dates so that you both actually take the time to relax. Why not head away from business talk and head to a museum or art gallery? Learn about new things together while finding out more about each other! It will probably do you both good to get away from your businesses for a while!
  7. If you are both inside at a desk or running around managing your business all day you must make sure you are in good physical shape. Whether you go on a bike ride, hike, or take part in a sport together you could both get active while learning more about each other. On the flip side, you may want a quieter date where you spend more time together and get away from the business altogether. One of the quieter date ideas is a games night together. Look into how to play a game with just two players, have some lovely food, and enjoy playing a game together. Just make sure that if you pick an active date idea you both want to do it and will enjoy it! 
  8. If you have been dating for a little while, a fantastic idea is to do the raffle idea. This is where you both have scraps of paper and write down different date ideas you would like to go on. You fold these pieces of paper and put them in a jar or container of some sort when it comes to planning a date you pick one of the pieces of paper and go on that date! Just make sure you both only put ideas that you will both be, at least, happy to try. This gives you both something to look forward to when you’ve been managing your staff and ensuring the successful running of your business all week. 

Many people feel that all entrepreneurs make a lot of money while their staff do all the work. Let’s be honest, we all know that is not true! There are times when you will work evenings or weekends and so your dates will have to be arranged around this and your need to sleep! You may have times when a date is interrupted with a panicked phone call from a staff member needing your support or your being called in at the weekend. Either way, you will both understand this and will find ways to ensure your dates still happen. 

Some Useful Websites to Meet and Date Single Entrepreneurs

      There are many, many dating sites out there which can sometimes make the online dating world a complicated place to visit! This used to be especially difficult when looking for something specific. However, these days it is much easier to find what you are looking for. If you are an entrepreneur and want to find another like-minded person to establish a friendship and, who knows, a romantic connection with it could not be easier! There are a couple of entrepreneur dating sites you could explore. If you head over to "Dating sites for and by entrepreneurs" you will find different dating sites for single entrepreneurs. You could also head over to one of the more well-known sites such as Match, Elite Singles, or Zoosk. These days you can refine your search on a dating website to ensure you find other educators to converse with and start a wonderful relationship!


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