What Strangers Taught Me About Matchmaking and Finding Your Person
In the last two and a half years, I’ve learned a lot about dating and relationships—but not through my own experience. Instead, I’ve had the privilege of talking with over a dozen singles who met through matchmaking.
They shared their stories with honesty—the highs and lows, the doubts, the moments that made them question everything, and the unexpected joy of finding someone who truly fit. These weren’t polished success stories. They were real, human journeys. And they left an impression on me.
Not because matchmaking is a perfect solution for everyone—but because hearing these stories made me a stronger believer in the power of trusting the process, getting clear on what matters, and staying open to possibilities.
So what have these strangers taught me about love, matchmaking, and finding “the one”? A lot more than I expected.
My Journey
When I joined The Matchmaking Company as a marketing specialist in late 2022, it was my first time experiencing the dating industry from the inside. As a millennial who created her first Facebook account in a college dorm room, matchmaking felt like unfamiliar territory—something I’d heard of, but never imagined I’d work alongside. Thankfully, I was hired for my digital marketing skills, not my dating expertise.
But with a long-standing curiosity about human behavior—why we choose who we choose, how we connect, what we long for—I saw potential beyond the job description. A matchmaking service felt like the kind of place where I could stretch both my creative mind and my interest in storytelling in a deeper, more meaningful way.
So when the opportunity came to meet clients who had found success through matchmaking, to sit across from them, hear their stories, and help share their experiences—I jumped in without hesitation. What started as a marketing task became something much more personal: a front-row seat to the quiet, powerful ways people find each other.
The Interviews (The Love Stories)
When I sit down to interview a client, I aim to keep it conversational. We start with the basics—some small talk, quick introductions—just enough to ease into something more personal. Then I walk them through the kinds of questions I’ll be asking.
I usually ask: What brought you to matchmaking? What was your dating journey like before joining? What were the biggest challenges? What were you hoping to find in a partner? Did you have any hesitations?
From there, I follow their lead—knowing when to dig a little deeper, and when to simply listen and let their story unfold.
What strikes me most in these conversations is the willingness to be open. It takes courage to talk to a stranger about love, especially when love has been hard. These exchanges can be emotional. Vulnerable. But they’re also incredibly generous—and it’s something I never take for granted.
Barbara’s Story
Barbara came to matchmaking after the loss of her husband. She had recently moved to a new state to be closer to her children, but quickly realized something was missing: companionship.
Zesty, warm, and full of life, Barbara wasn’t about to let age slow her down. She wanted to stay socially active, explore new connections, and yes—open herself up to love again.
When her matchmaker, Lori, introduced her to Ron, Barbara was skeptical. Before they ever met, she learned he drove a red sports car—and instantly made assumptions.
“I wasn’t prepared for what I met when I met Ron. I thought I was going to meet someone with a little white goatee and gold chains because he drove a red Corvette. And I did not want to meet someone who drove a red Corvette. I thought for sure this was going to be someone full of himself with a string of women just dying to ride in his Corvette.
I said, No, that’s not for me.
But Lori didn’t give up. She said, This guy is special. And so are you. I want the two of you to meet.
So we did.” -Barbara
When they met in person, Barbara quickly realized she’d misjudged him. Ron wasn’t flashy or conceited—he was calming, thoughtful, and surprisingly lovable. Their conversation flowed. They discovered a mutual love for good whiskey and shared interests that kept them talking long after the check arrived. The chemistry was undeniable—and Barbara decided to stick around and see where things might go. They’re married now.
What stuck with me from Barbara’s story was her willingness to trust the process. She trusted her matchmaker. And in a world of dating apps, where we’ve been trained to disqualify people over surface-level details, that kind of trust is powerful.
Apps reduce people to profiles. Limited info, quick swipes, snap judgments. But matchmaking is different—because there’s someone in your corner, someone who says, “I’ve met this person. I think they’re a good match for you.”
And more often than not, when clients trust that guidance, good things happen.
Kris’s Story
It doesn’t have to be a perfect start. That’s the beauty of dating—when you take the pressure off, there’s more room for authenticity and connection.
Kris, an established pilot and father, joined matchmaking after going through a divorce. He’d spent several years building a meaningful life as a single dad and felt ready to find a partner who could truly complement the life he’d created for himself and his kids.
One evening, his matchmaker called with something exciting. She had someone she wanted him to meet—tonight. Kris was leaving the next morning for a work trip, but thought, Why not? So he said yes.
Meanwhile, Christina was driving with her kids when Kris reached out. She had no shoes on and wasn’t exactly in “first date” mode. But with her faith guiding her, she said yes too. “Let’s just meet for a quick hello.”
So they did. They sat on a bench, shared lemonade, and talked. It was simple. Spontaneous. Unpolished. And exactly enough to spark something real.
“I think back to it—if I had been stubborn and just said, “No, I need to get ready for work. I’ll talk to her when I get home next week.” We might not be here.” -Kris
What I love about their story is how willing they both were to show up—messy, unprepared, and totally themselves. No fancy setting, no pressure to impress. Just two people being open to connection.
That kind of flexibility and self-assuredness? It’s a quiet superpower in dating.
Watch Kris & Christina’s story
Shannon’s Story
Shannon, a successful business owner in her 50s, came to matchmaking after deciding that dating apps simply weren’t her style. The endless swiping felt impersonal, transactional. What she craved was something more grounded—something real. From the start, she felt a sense of relief in the process. Her conversations with the matchmaking team were personal, thoughtful, and refreshingly human.
Though hesitant at first, Shannon knew she wanted support. She had been married before and recognized that finding the right person this time around would require more than instinct—it would require clarity, intention, and a second set of ears and eyes.
“The matchmaker asked me: ‘What do you need in a person?’ Not what they should look like—what do you truly need?’” -Shannon
That question changed everything.
She let go of the long-standing checklist—the tall, dark, and handsome ideal—and wrote down what really mattered. That shift, from wanting to needing, made space for something meaningful to enter.
Her matchmaker, Mika, introduced her to Kevin, a fellow business owner with a calm, grounded presence. They were different in some ways, but shared an openness—an ease with trying new things, and a mutual respect for each other’s lives and perspectives.
Shannon saw what truly mattered in a relationship, and it wasn’t what she expected.
“He gives me safety, security, and space to be who I am. That’s love.” –Shannon
What stayed with me about Shannon’s story was her clarity—the kind that only comes from doing the inner work. She didn’t confuse desire with direction. Instead of letting old patterns or idealized preferences steer the course, she stayed open to her matchmaker’s guidance and trusted her own deeper knowing. By loosening her grip on the superficial, she created space to focus on what truly mattered—not distractions, but dealbreakers.
The Myths You’ve Got to Stop Believing
If there’s one thing these stories have taught me, it’s that love doesn’t show up the way we think it will.
Barbara taught me that people are more than the boxes we put them in. That gut-level resistance we feel based on someone’s car, job, or hairstyle? It might be nothing more than fear wearing the mask of certainty. Love asks us to stay curious—even (and especially) when we think we already know.
Kris and Christina showed me that love doesn’t require a flawless entrance—it just needs honesty. First dates don’t need ideal lighting or a perfect outfit. They need presence. Openness. A willingness to meet someone exactly where you are. That bench-side lemonade date? It worked because both of them showed up as real people—not polished versions of themselves.
And Shannon’s story—perhaps the most universal of all—taught me that our desires aren’t always a compass. Sometimes they’re a distraction. There’s a quiet bravery in asking, “What do I truly need in a partner?” and being willing to let go of old fantasies to make space for real connection.
So if you’re in the thick of dating right now, or just starting to think about it again, here’s my honest advice:
Let go of the myth that love arrives looking exactly how you pictured it.
Let go of the idea that chemistry is either instant or nonexistent.
Let go of the belief that you have to figure it out all on your own.
The real “one” probably won’t check every box on your list—but they’ll meet you where it counts.
And when that happens, it won’t feel like settling.
It will feel like coming home.
