What’s it Actually Like to Work with a Matchmaker?

Answers to the Most-Asked Questions

At The Matchmaking Company, dating isn’t left to chance—or to swiping endlessly on apps. It’s about having a real, one-on-one relationship with someone who’s fully invested in helping you find love. Working with a matchmaker means teaming up with a professional who takes the time to understand you: your values, your goals, your story.

This isn’t about algorithms or random pairings. It’s about meaningful introductions, thoughtful conversations, and real human connection.

So what’s it actually like to have a matchmaker by your side? We sat down with The Matchmaking Company’s Director of Matchmaking, Kathrine Wilson, to unpack the full experience—from your first consultation to that moment when everything just clicks.

What is working with a matchmaker actually like?

KW: A lot of people are surprised by how personal—and how empowering—the experience really is. When you’re working with a matchmaker, you’re not signing up for an app or getting lost in a giant database. You’re starting a professional relationship with someone who genuinely wants to understand you, your story, and what you’re truly looking for.

It begins with a real conversation—not a form, not a swipe. You meet face-to-face with a New Client Advisor and talk about your relationship history, what you’ve learned, and what kind of future you want. That becomes the foundation for everything that follows.

We build your profile together—not just stats or preferences, but your personality, communication style, and what makes you feel seen in a relationship. That’s what leads to thoughtful, meaningful introductions.

Matchmaking is never rushed. Each match is selected with care, using both experience and intuition. We focus on deeper things like values, pace, and long-term goals.

After each date, we check in. That feedback sharpens the process—and sometimes, it reveals unexpected clarity about what you really want.

This is a collaborative journey. You’re in control, but never alone. You’ve got someone in your corner who truly cares—and that changes everything.

To me, working with a matchmaker means having someone in your corner who’s invested, experienced, and deeply committed to helping you find something real. And that kind of support changes everything.”

What do matchmakers look for when finding the right match?

KW: When people ask what we’re really looking for in a match, I always say—it’s not just about what’s on paper. Sure, we consider lifestyle and compatibility, but it’s much deeper than ‘likes hiking’ or ‘enjoys travel.’

We start by understanding you as a whole person. Not just your dating history, but how you live, what drives you, and the kind of relationship you want to build.

From there, we look for people who align with your energy, values, and pace. That doesn’t mean a clone—it means someone who complements you. Someone whose goals line up with yours and fits into your actual life.

It’s part intuition, part experience, part strategy. We’re not guessing—we’re drawing on years of insight and countless conversations to say, “These two could really work.”

It’s not about perfection. It’s about compatibility. Someone who brings out the best in you and feels like a natural fit—that’s the connection we’re always aiming for.

When you’re working with a matchmaker, you’re not just being paired based on shared interests. You’re being introduced to people we truly believe could build something meaningful with you—and that belief is grounded in who you are, not just what you like on the weekends.

How do matchmakers decide who is compatible?

KW: In matchmaking, compatibility isn’t about surface-level traits—it’s about real alignment in areas that shape lasting relationships.

At The Matchmaking Company, we focus on areas like values, relationship goals, lifestyle, emotional readiness, and communication style. 

We ask: What does partnership mean to you? What does commitment look like? Are you a planner or more spontaneous? How do you give and receive emotional support? Do you want something slow-building or fast-moving?

Once we understand your core, we look for someone who aligns where it matters. You don’t need all the same hobbies—what matters is how you show up in a relationship. Do your communication styles work together? Do your goals match?

A big part of our job is also protecting you from mismatches that might seem exciting but lack deeper compatibility. We’ve seen how misalignment—especially in values or emotional readiness—can derail promising connections.

Working with a matchmaker means you’ve got someone focused on what truly counts. We’re filtering for compatibility and chemistry—so you’re not just chasing a spark, you’re building something that can last.

What are the biggest myths about working with a matchmaker?

KW: A common myth is that matchmaking is old-fashioned—something for people who can’t meet anyone or something your grandmother did. That couldn’t be further from the truth.

Modern matchmaking is intentional and highly personal. Our clients are successful, self-aware, and serious about finding something real. They’re not struggling to meet people—they’re done wasting time on the wrong ones.

Another myth? That we match people based on a checklist. It’s not about identical hobbies or zip codes. We go deeper to understand your values, your non-negotiables, and where you might be open to the unexpected. Great matches often come from surprising places.

There’s also the idea that once we introduce someone, our job is done. Not true. We stay involved—debriefing after dates, gathering insights, and refining the process.

A lot of people come to us burned out by apps and gameplaying. What they find at The Matchmaking Company is a thoughtful, human approach that helps them reconnect with what they truly want.

How do matchmakers handle clients with different dating goals?

KW: One of the first things we ask is not just who you want to meet—but what kind of relationship you want. Some clients are ready for marriage, others want a long-term partner without a timeline, and some simply want a stable, loving connection. That clarity matters.

There’s no cookie-cutter approach. Every client is different, and so is the plan we build. We start by listening—really listening—to your relationship history, mindset, and goals. Are you divorced and dating again? Ready to start a family? New to serious relationships? Wherever you are, we meet you there.

Once we understand your vision, we look for people aligned with it. Chemistry is great, but shared direction is essential. If someone wants a different future, we’re honest about that—no confusion, no surprises.

Our process is intentional and transparent. Your goals guide every step, and we make sure each introduction is a step toward the relationship you truly want—not just one that checks boxes.

What if the first match doesn’t go well — what happens next?

KW: I wish every first introduction sparked fireworks—but let’s be honest, that’s not always how it happens. And that’s completely okay. Matchmaking isn’t about instant perfection—it’s a thoughtful, responsive process that moves you closer to the right person.

Sometimes a first introduction just doesn’t click. Maybe there’s no chemistry, or your priorities don’t line up. That’s not failure—it’s insight. Every introduction teaches us something. What felt good? What didn’t? Did you feel seen? Were your values aligned?

After each date, we debrief with care. Your feedback isn’t just noted—it shapes what we do next. Maybe you’re craving someone more expressive, or discovering preferences you hadn’t considered. That’s real growth.

Intentional dating means some mismatches are inevitable. But with a matchmaker, you’re not navigating them alone. You’ve got a pro beside you—asking smart questions, spotting patterns, and adjusting in ways that move you forward.

Even the “no’s” help us get to your “yes.” It’s not trial and error—it’s refinement. That’s where the magic really happens.

How much say do I have when I’m working with a matchmaker?

KW: A lot! I always tell clients—this is your love life. We’re here to support you with insight and strategy, but matchmaking is a partnership. You’re not a passenger—you’re in the driver’s seat.

From day one, your input shapes the process. You help build your profile, define preferences, and set the pace. Want more time between matches? Want to adjust your parameters midway through? We adapt. This isn’t a one-size-fits-all system—it’s built around you.

If something doesn’t feel right, we want to hear it. Your feedback isn’t just collected—it directly informs how we move forward.

Unlike dating apps, where you’re left guessing, matchmaking is built on dialogue. We ask, we listen, and we refine. And while we may encourage you to stay open-minded, we never want to pressure you to accept a match you’re unsure about.

Our goal isn’t to take over—it’s to enhance. To make dating more focused, less draining, and genuinely meaningful. Your voice matters—and it’s central to every step of the journey.

What makes a good match beyond just common interests?

KW: Great question—because shared interests might start a conversation, but they don’t sustain a relationship. A good match goes deeper than surface-level compatibility. It’s about how two people connect and function together in everyday life.

We look for someone whose values align with yours. Someone who communicates in a way that makes you feel understood. Someone emotionally available, who supports you in the ways you need. That’s what creates safety, connection, and lasting love.

We also look at rhythm. It’s not just, “Do you both like dogs?” It’s, “Do your lives fit together?” Shared priorities and lifestyle alignment matter more than matching hobbies. Chemistry without that foundation leads to friction. But when someone fits into your world naturally, everything flows.

I’ve seen opposites thrive—extrovert and introvert, traveler and homebody—because they shared core values, communication styles, and emotional presence. That’s the kind of sync we aim for.

With a matchmaker, you go beyond “Do we like the same things?” and into “Can we build something real?” We’re not just swiping—we’re listening, connecting dots, and finding that deeper fit that really matters.

What’s something most clients don’t expect about working with a matchmaker?

KW: One of the most unexpected—and beautiful—parts of matchmaking is how much clients learn about themselves. Most come in thinking it’s just about finding someone else. But what unfolds along the way can be just as meaningful.

This process holds up a mirror. You’re asked questions you may not have considered in years—about emotional safety, vulnerability, and what kind of love actually feels good. These reflections come up naturally in conversations, feedback, and patterns we notice together.

Many clients are surprised when their preferences evolve. They arrive with a fixed idea of what they want—shaped by past relationships or old habits—and discover those wants don’t match what they truly need. That clarity builds confidence and intentionality.

I often hear, “I didn’t expect this to be such a growth process.” And it’s true. We’re here to help you find a partner, but also to help you reconnect with yourself—your patterns, blind spots, and strengths.

Matchmaking isn’t therapy—but it is therapeutic. You’re being listened to, challenged, and supported. That self-awareness doesn’t just lead to better matches—it helps you become a stronger, more present partner when the right relationship begins.

How long does it usually take to find a match through a matchmaker?

KW: One of the most common questions we hear is, “How long is this going to take?” And I get it—after exhausting rounds of dating apps and setups, people want hope that this process will be different.

The answer? It varies. Some clients meet someone great right away. Others need a few introductions before something clicks. It depends on your preferences, your openness to the process, and how your preferences and needs align with the current client pool.

What’s different here is the intention behind every introduction. We’re not making random pairings. We’re focused on real alignment—so even if it takes a bit longer, the overall experience is more meaningful and effective.

I tell every client: you’re not just dating—you’re dating with direction. The goal isn’t speed. It’s finding a partner who brings real joy, and a relationship that lasts. 

Why choose a matchmaker instead of using dating apps?

KW: Dating apps can feel like a full-time job. You’re swiping, messaging, analyzing every emoji, and still left wondering what someone’s really looking for—or if they’re even serious. Most people come to us because they’re tired of all that noise. They want something more focused, more human, and more aligned with their long-term goals.

When you’re working with a matchmaker, you’re not guessing anymore. Every introduction is intentional, grounded in real compatibility—not just algorithms or clever bios. You’re meeting people who are also serious, who’ve been vetted, and who want the same kind of relationship you do.

And maybe most importantly, you’re not alone in the process. You’ve got someone by your side helping you reflect, learn, and stay grounded. We’re not just matching people—we’re guiding them through one of the most important journeys of their lives.

That support, that clarity, and that sense of direction—it’s what makes matchmaking so different from the dating apps. It’s not just about meeting someone. It’s about meeting the right someone

Ready to Try a Different Kind of Dating Experience?

If you’ve been feeling like your dating life just isn’t cutting it, you’re not alone—and you’re not out of options. At The Matchmaking Company, finding a relationship isn’t a mess of random setups or algorithms—it’s a guided process designed to help you meet someone truly compatible.

Working with a matchmaker isn’t about giving up control. It’s about gaining a partner in the process—someone who gets what you’re looking for and is committed to helping you find it.

Whether you’re just curious or seriously ready for a change, The Matchmaking Company offers a thoughtful, personalized approach that puts connection first. Real people. Real conversations. Real possibilities.

You don’t have to keep doing this alone—and you don’t have to settle. 

Our team is here to help you take the first step toward finding the compatible relationship you’ve been waiting for. 

Begin your matchmaking journey today.