When the world's well-heeled want love, they call Jennifer Donnelly.
The founder of The Ultimate Matchmaker understands what truly drives high-net-worth individuals in love and why it’s a serious investment in happiness.
So serious that clients have paid Donnelly over $500,000 to help them find long-lasting partners, and she boasts a 98% success rate.
Needless to say, Donnelly isn’t competing with Bumble Inc (NASDAQ:BMBL) or Match Group (NASDAQ:MTCH), owners of Tinder and Hinge. Unlike those app-based platforms that rely on swiping and algorithms, Donnelly offers a highly personalized, discreet, and relationship-focused service for affluent clients—making her business a bespoke experience rather than a volume-driven dating app.
See Also: Match Group To Pay $14 Million In FTC Settlement Over Deceptive Practices
You’ve been a professional matchmaker for over 20 years. How did you start?
In my experience, the starting line of any career begins by recognizing your own innate talents in everyday life. For me, college was when I first began to understand the deep dynamics of human connection. From there, practice made progress. I took those natural gifts and transformed them into a national brand, which required courage, consistency, and an"every person matters" mentality. Building something lasting didn't happen overnight. It meant stepping off the beaten path and building something passionately, authentically, and with a deep desire to always grow and refine both personally and professionally.
After graduating, I worked at a traditional matchmaking firm, which gave me a solid foundation but didn't reflect the elevated, highly personalized service I offer today. I developed my own strategies and process, leading to a 98% success rate—the method is proprietary, but it works. I took a break from the industry to focus on my children, then received a call from someone who remembered my talent for matchmaking. He introduced me to a high-net-worth friend seeking a strategic search for a partner. That client found his life partner through my process and referred others. My business grew entirely through referrals, and it still operates that way today.
What’s the screening process like?
We are highly selective. I conduct at least two to three in-depth interviews with every prospective client before we start the process of finding potential matches for them. It is crucial to understand who they are and what they need fully. If their needs don't align with my moral compass, I don't take them on. Extraordinary careers and financial success do not necessarily equate to charm or the ability to perform well as a ‘good date.’
I deal with some incredibly charming people. However, sometimes past dating situations have allowed people to become disheartened-that's where we come in. I instantly spot where someone may need to collaborate. My job is to help reignite their natural charm, which happens once positive dating experiences occur. Everyone has the capacity to reconnect with their joyful, true self. One of my favorite parts of matchmaking is guiding clients who've mastered professional success to thrive in their love life, too.
I read that 60% of your clients are men and 40% women. What are the men looking for? What are the women desiring?
This is a challenging question with many layers. But if I had to distill it, both successful men and women are looking for authenticity, integrity, self-awareness, confidence, and emotional growth. These core traits are universally desired across the board. That said, successful women often seek men who are confident in themselves, who are inspired — not intimidated — by their accomplishments, and who still embody a romantic,courtship-driven mindset. On the other hand, successful men tend to look for women who truly see them — who connect with the man, not the lifestyle he may provide.
Nowadays, women often out-earn their potential male partners. Does this trend affect who they match with?
That's an interesting observation. While I can't speak to every statistic, what I can say is this: Men, just like women, are redefining their roles in the modern world. We're seeing a cultural shift across the globe. Financial dynamics in relationships are evolving, and while that can present new challenges, it can also open doors to more balanced and intentional partnerships. Ultimately, values, emotional intelligence, and shared vision tend to outweigh income — especially for those seeking a lasting relationship.
Why do your clients need a matchmaker? Are there any reasons besides the typical ‘busy careers’ or refusal to use apps (i.e., Raya)?
Yes, absolutely. Privacy is a top concern for my clients — and dating apps simply don't provide that. Many of our clients are public figures or hold high-profile roles, and discretion is critical. Also, time is a limited resource. Our services are tailored to optimize both time and opportunity — ensuring that each introduction is intentional, meaningful, and identity-protected.
Are your clients guaranteed dates?
We take the time to thoroughly vet our clients, which is why we're selective about who we work with. By the time we reach the actual matchmaking stage, we've already built a solid foundation — we understand who they are, what they want, and who could be a great fit. That's why our success rate speaks for itself. It's very rare that we can't find the right connection.
How big is your firm, and are you hiring?
We’re a mid-sized agency with a close-knit, collaborative team. While we're not actively hiring at the moment, we're always open to connecting with individuals who are genuinely passionate about matchmaking and aligned with our values.
Any unusual requests from clients?
In over twenty years of matchmaking, I’ve definitely encountered my fair share of unusual requests—everything from extremely niche hobbies to highly-specific lifestyle requirements. I always say, as long as the request comes from a place of authenticity and respect, I'm open to exploring it. But if something doesn't sit right with my moral compass—whether it feels disrespectful or unrealistic —I simply won't take it on. My job is to help people find meaningful, lasting connections, not just check boxes. And yes, in most situations, even the most unique and unbelievable requirements do come true! I wish I could give you an example, but being discreet is one of the most important parts of what I do!
Now Read:
Image courtesy of Elizabeth Lavin
