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Dating Tips for Entrepreneurs From a Top Matchmaker

Violet Lim, an Entrepreneurs’ Organization (EO) member in Singapore, is CEO and co-founder of Lunch Actually Group, a dating service that connects eligible singles in a caring, comfortable, convenient way. As an entrepreneur who understands the pitfalls and best practices of dating, we asked Violet what entrepreneurs should focus on when seeking their significant other. Here’s what she shared.

How do you coach entrepreneurs and business owners as they embark on their dating journey?

Many singles believe they are single because they have a “meeting” problem. As an industry veteran, I’ve learned that finding the right one is not only about meeting the right one. It’s also about being the right one and choosing the right one. Pose these questions:

  • Are you the right one yourself?
  • Do you have the right mindset and skill set to attract the right one?

Once your mindset shifts, you’ll present the best version of yourself, which will attract quality singles. You can grow as a person to be more confident and attractive, not just as a business leader, but as a dater.

Consider this: You have one-year, three-year and five-year plans for the direction and growth of your company. Similarly, it’s just as important to have plans for your personal and family life. Things don’t happen by accident, you make them happen by planning and executing well.

What are some dating best practices for entrepreneurs?

Many professionals avoid dating apps because photos are displayed and it would be awkward if clients come across your dating profile. Business owners often don’t have time to scroll through profiles, make conversation and keep the other party interested before finally meeting.

There are more convenient platforms: matchmaking services, meetup events and interest groups. Do your research, and use the dating service best-suited to your lifestyle.

In the corporate world, we conduct performance reviews to hear what colleagues say about each team member, gather constructive feedback and set goals. Same with dating! It’s a best practice to seek honest feedback from friends and family, to identify any dating blind spots and get feedback on your dating history.

This will put you in control of your dating journey. Reflect on whether you have the right mindset and readiness to date, especially if you’ve had painful relationships in the past.

What mistakes do entrepreneurs make in the dating space?

1. Unrealistic or superficial preferences. When looking for your life partner, do you focus on superficial criteria, or look for significant traits that would sustain a long-term, meaningful relationship?

Warren Buffett once said that the biggest decision of your life is who to marry―it impacts both personal and business success. I advise clients to be truly aware of what they’re looking for in a partner, beyond superficial preferences.

If you’re focused on body type, height or hairstyle―nice-to-haves that ultimately don’t contribute to a meaningful relationship―you’ll eliminate a lot of potential partners and jeopardize your chances at finding love.

2. Checklist Syndrome. If you reject most potential dates, you may be guilty of Checklist Syndrome. Revisit your criteria, paying particular attention to how many are flexible versus inflexible. Adjust accordingly.

I tell clients, “The yardstick on whether to go on a second date is not how much you like the person, but how little you dislike the person.”

If you’re on the fence, go on the second date!

3. Examine past relationships. Do you always choose the wrong type? For example, many women like “bad boys” because they are unpredictable, exciting and full of surprises. But if you always date bad boys, and it never works out, it’s time for a change.

Past relationships teach lessons about what you should―or shouldn’t―seek in a future partner. Reflect and learn from your exes, and use those lessons to make better decisions in your love life.

How does a dating service enhance the dating experience?

Working with a credible dating service gives you personalized service, safety, privacy and saves valuable time.

We can access the right matches and guide you through the process, inspiring you to grow and become a better dater. We can help pinpoint your dating blind spot, advise you on acing a date and build your dating confidence.

What’s your most memorable match?

Probably our first couple who got married. On the surface, they were an unlikely match, but we paired them because we believe that ultimately, compatibility in values makes the best couple.

Chris is a lawyer. When we matched her with Ben, she was furious: Why did we match her with a performer who juggled and rode a unicycle? Because we had met with both of them and realized that they shared similar values and senses of humor―and were likely highly compatible. You see, Ben isn’t your typical entertainer: He earned a master’s degree from Oxford.

After much persuasion, Chris reluctantly went on the date. They hit it off brilliantly, got engaged within three months, married within one year and now have two beautiful daughters. And they probably wouldn’t have crossed paths without our help!

To cynics who say that matchmaking takes the romance out of dating, Ben says, “Love is love, no matter if you meet at a bus stop, a bar or through a dating service!”

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