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In the world of matchmaking, there’s no one quite like Jennifer Donnelly. Since 2000, the highly profiled dating guru has been connecting some of the world’s most influential people through her platform The Ultimate Matchmake, with discretion and thorough analysis—and we had to know more! From dating do’s and dont’s to success stories—and tips for those of us in the “lonely hearts club”—we sat down with the romance expert to learn all about finding a perfect match.
How did you get into luxury professional matchmaking?
This was never a career choice for me in the traditional sense—it was something that has always been a part of me. I was a connector before I even understood what that meant. For example, the neighbor who brought me a snow cone when I was 8 years old? He’s been happily married for nearly 20 years to a woman I introduced him to—and they have 2 children together. Connecting people up just came naturally, and I was surprisingly good at it—even from a very young age. As I entered the professional world, that gift only grew as my success in matching continued. I ended up pairing some rather affluent couples who graciously referred me to others, and from there my childhood goal of helping singles find love has flourished beyond what I could have ever hoped for. Not many people can say they’re living their dream and pursuing their passion every day—so I never take for granted how fortunate I am to do exactly that.
You’ve been a dating expert since 2000. What are some dating behaviors, or overall ways you’ve seen dating change in the last 25 years?
The biggest shift? Accessibility. In today’s digital world, singles can view hundreds of potential matches with just a swipe. What was once cherished—the thrill of pursuit that relied upon genuine connection and emotional vulnerability—has often been replaced by instant gratification. In-person interactions can feel more transactional, and true connection is becoming increasingly rare. We now carry dating apps in our pockets like a mobile nightclub, but that convenience often comes at the expense of depth. People are giving more too quickly, settling for less, and losing sight of what they truly want—and deserve—in a partner. That said, the clients I work with operate in a different realm. For them, privacy is paramount and time is precious. They’re not looking for a sea of options—they’re looking for the one who fits. And I love that. I’m selective about who I work with for that very reason. My business model only works when we’re aligned in our mission: to find a love that is meaningful, lasting, and real.
Jennifer Donnelly (Courtesy of Jennifer Donnelly)
What is an essential tip everyone should keep in mind on a first date?
Don’t walk into a new connection carrying the weight of your past. The person in front of you is not your ex. Keep your mind open and your energy light. People are naturally nervous on first dates—offer a little grace. Don’t overanalyze every word; just stay present and enjoy the moment. You can’t feel or evaluate true chemistry if you’re too busy being critical.
What are some dos and don’ts when dressing for a first date?
Dress in a way that reflects your confidence, your taste—and your intention. First impressions matter, but shouldn’t be overdone. You don’t need to reveal everything to be captivating. The sweet spot lies in showing you’ve made an effort without trying too hard: polished, appropriate for the setting, and true to your personal style. Mystery, elegance, and authenticity never go out of fashion—and confidence always reads best when it feels effortless.
Do you also give your clients styling advice—or have any fashion-related success stories from matchmaking over the years?
Typically, my clients already have a strong sense of personal style, so fashion advice isn’t something they often need. But every now and then, I’ll weigh in. Just today, one of my male clients sent over a few date-night looks from a couple of luxury designers, and we landed on a final pick together—Tom Ford. It’s a fun part of the process, but for me, it’s less about giving advice and more about refining what’s already there.
How does a matchmaker dress for work? Do you have any go-to styles or outfit formulas?
I dress with intention—always polished, always professional. My style sends a clear message: I’m here to work, to deliver, and to be taken seriously. There’s no room for ambiguity. My go-to? A perfectly tailored Alexander McQueen suit—tructured, elegant, and powerful. Over the years, I’ve collected nearly every color, from classic black to vibrant yellow, deep navy, and even signature red. I typically pair it with a timeless Hermès Birkin and a clean Jimmy Choo pump. It’s not about flash—it’s about presence. When I dress like the expert, I can walk into any room already aligned with the standard my clients expect.
What is one of your greatest matchmaking success stories—even though you have so many!
Honestly, it’s impossible to choose just one. With a 97–98% success rate, each story holds something special. But one recent moment stands out: a client came to me with a long list of non-negotiables—he was firm, focused, and hesitant to compromise. I introduced him to one person. Just one. Today, they’re in a deeply committed relationship, and even his board has noticed the change in him… for the better, of course. His assistant called me recently and said, “Who is this man, and what have you done to him?” And when the client himself told me, “I think you may know me better than I know myself,” I simply said, “Isn’t that what you hired me for?” Those are the moments I live for.
For those of us in the “lonely hearts club,” how can people stay hopeful that our perfect match is out there?
Never lose hope. Just because you haven’t met them yet doesn’t mean they don’t exist. How exciting is it to think that at this very moment, someone out there is wondering what it would be like to be with someone exactly like you. That’s not just wishful thinking—that’s reality. Having been in this business practically my whole life, I can promise you: love is out there. There truly is someone for everyone. It’s not about when—it’s about who. And when the right person comes along, all the waiting will have been worth it.
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