Toronto, ON — These days, dating can feel confusing and even risky. Many professionals say they’re tired of dating apps, ghosting, and guessing someone’s true intentions. That’s why more and more high-achieving people are turning to something that feels safer, calmer, and smarter: executive matchmaking.
One company leading this change is Legacy Matchmaking, a private matchmaking firm that works with business leaders, professionals, and people who want more than just love, they want a lasting partnership that supports their future goals.
“Our clients don’t come to us because they can’t get dates. They come to us because they’re tired of filtering through people who aren’t genuine. Dating is exhausting, especially when you’re working 50+ hours a week.” Lance explained.
Lance brings a deep background in both business and wellness. Before joining the Legacy team in Toronto, he worked in corporate consulting and went on to become the founder of one of the largest sexual health and wellness companies in the Caribbean. His mix of heart and high standards helps clients feel both seen and protected.
“Time is the one thing our clients can’t outsource or buy back. Every year spent in the wrong relationship, or avoiding one altogether is time they can’t get back. We help them make the right choice (for them),” said Gibbs.
Gibbs further explained, “No one dreams of reaching the top only to find themselves celebrating alone. After a long day, success feels hollow if there’s no one waiting at home. And when the next invitation arrives with a ‘+1,’ your Frenchie shouldn’t be your best option.”
At LegacyMatchmakers.com, every client is carefully interviewed, and all matches are thoughtfully hand-picked and background-checked. The team doesn’t rely on apps or random algorithms. Instead, they focus on emotional intelligence, privacy, and matching people who share the same goals and values.
The firm also uses a proprietary framework called The Rich Nervous System™, which helps some clients prepare emotionally for the kind of love that lasts. Legacy’s matchmaking process is shaped in collaboration with licensed therapists, relationship coaches, and legal advisors. The firm also maintains a trusted network of these professionals to support special cases that require deeper guidance or care.
Legacy’s clients come from all over North America and Europe, including professionals in finance, medicine, law, tech, and even public office. Many are successful but say they feel
disconnected or tired of the dating scene. For them, Legacy offers a different path, one that feels both strategic and sincere.
In fact, a Pew Research study recently showed that over 60% of high earners are unhappy with dating apps. Their biggest worries? Safety and not knowing who to trust. That’s why the Legacy approach feels like a breath of fresh air.
“Matchmaking used to be something the ultra-wealthy did behind closed doors,” says Lance. “Today, more professionals are treating it like any other form of personal investment—just like hiring a financial advisor or a trainer. But instead of money or muscle, we’re helping them build something far more personal: aligned, lasting relationships. We take time to understand their values, goals, and non-negotiables, then introduce them to high-caliber matches well beyond their usual circles.”
Legacy Matchmaking is helping these professionals build relationships that grow from a more thoughtful way to connect; one that aligns with both the heart and the life its clients are building.
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