Love or Loss: How Fares the Dating Scene for a CEO?

As Valentine’s day approaches, along with it comes either a feeling of excitement or absolute dread. Perhaps more so for those at the top of the ladder, where work can take priority, and concerns over the business can cloud the vision of potential dating and all the qualms that come with it; it begs the question, how much harder is it for single CEOs in the venture of romance?

At the end of the day, the need for love and companionship is universal, and those at the top are not indifferent to its charms. If there’s anything to take away from today’s success stories and how they relate to love, it all comes down to patience, understanding and mutuality. The ideal partner will value your work and your success as if it were their own and become a piece of your identity, melding work and relationships together so that they complement rather than detract from each other.

Where to start

From a CEO point of view, perhaps the worst obstacle is the reluctance to start, given all the risks and hurdles involved. It’s much easier to stay single than take on the reigns of a relationship when there’s all too much on your plate already. If you don’t know where to begin, help comes in many forms: for example, self-help dating books specifically targeted at CEOs and other leaders of their respective businesses, and various dating websites and apps with similar target audiences, including Millionaire Match, which works just as the name suggests.

Probably the most beneficial method is to ask friends to introduce you to someone they know, with the majority of connections being made through this method, as shows in its survey. Common ground is a must: if you’re all about business, it makes sense to find someone who shares your ideals with you. It comes with the territory that you meet some of your best acquaintances in your familiar social circles, so the spark of romance can form with someone you see eye-to-eye with above all else. A friendly referral can ensure just that, as your friends will know you best and be able to find a good match – from there, though, it’s up to you.

Making it work

As with anything else, dating comes with too many ups and downs to count. For example, time management is imperative. A potential partner will have to understand when work comes first, dates could be late (or even missed entirely); finding a balance for both parts of life is crucial. A busy schedule leaves little time for that initial search, and you need to ensure that you’re with someone you can trust. Maintaining flexibility, even in small amounts, can make a big difference.

However, there are the upsides as well, including what you can bring to a relationship from your position. With your work come the skills of a leader, a clear communicator, and the confidence needed to make things work – provided that a first step is taken. You also have the wherewithal to motivate your partner to be the best they can be – similar to how you handle those you oversee on the job. The talents you use on a day to day basis are transferrable to be used in this kind of situation, so making the most of them is essential.

As a professional, you’ll also know the value of learning from your mistakes. The best lessons come from blunders, and for every awkward or unsuccessful date you go on, there’s something to pick up and use to help you prepare for the next one. Remaining optimistic is key.


With the right mindset, anything is possible. If you walk away with any advice in mind, it’s not to give up. You wouldn’t give up so easily on a business transaction or venture, so why love?

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