Alright – so today we’ve got the honor of introducing you to Dara Rahill. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Dara, thanks for joining us today. Alright, so you had your idea and then what happened? Can you walk us through the story of how you went from just an idea to executing on the idea

My journey into matchmaking started long before I officially launched my company. My background as a psychologist gave me deep insight into human connection, and as I transitioned into matchmaking, I worked my way up to becoming the Head of Matchmaking Partnerships for the largest matchmaking company in the U.S. Meanwhile, as a passion project, I was building a thriving community of singles in Philadelphia, organizing events, and seeing firsthand the gaps in the dating landscape. That’s when I realized—Philadelphia needed a local matchmaking service that truly understood its people.

I kept hearing from accomplished professionals who had tried national matchmaking firms, only to feel disconnected from the process. They wanted someone who knew the city, who had real relationships within the community, and who could offer a hands-on, personalized experience. I grew up in this area, I love this city, and I knew I had the expertise and network to fill that gap. That realization made my decision clear—I was going to build my own matchmaking company.

Once I made the choice, everything happened fast. The very next day, I filed for my LLC and started brainstorming business names. Initially, I played around with clever and catchy names, but ultimately, I wanted my business to stand on integrity and accountability. That’s why I named it Dara Rae Matchmaking—because when your name is on the line, you hold yourself to the highest standard.

From there, I built the foundation: designing a website, selecting software to organize my growing network, and refining my matchmaking process. One of my biggest challenges wasn’t matchmaking itself—I knew how to connect people and guide them toward relationships—but learning how to sell my services. I had never asked anyone to pay for anything before, so I took a course called Ethical Sales for Matchmaking. It taught me that selling isn’t about convincing—it’s about identifying the right fit, understanding a client’s needs, and offering a service that genuinely benefits them.

Another key step was defining my ideal client. Who could I serve best? Who would benefit most from my approach? I focused on people with a growth mindset—those who weren’t just looking for a match but were open to learning, evolving, and becoming a better partner themselves. I also wanted to work with people I genuinely liked because matchmaking isn’t transactional for me—it’s personal. I invest time, energy, and emotion into my clients, so I needed to work with people whose stories I cared deeply about.

The first few months were a whirlwind. I was navigating client acquisition, refining my strategies, and streamlining operations. I was lucky to have incredible mentors who shared lessons from their own journeys, helping me avoid common pitfalls and structure my services effectively. Within months, demand exceeded my capacity, and I had a waitlist. That’s when I brought in Nicky Gordon, an experienced matchmaker and certified relationship coach, to join my team. Her expertise allowed us to serve more clients without compromising the personal, high-touch experience that sets us apart.

As the business grew, I had to learn how to delegate—handling social media, client outreach, and admin tasks while still focusing on what I do best: matchmaking. We integrated automation for onboarding new database members while ensuring every client still got a highly personalized experience.

Another key lesson? Just putting two people in a room isn’t enough. That’s why our process includes strategic dating guidance. Whether helping a client re-enter the dating world after a long marriage or offering insight on communication styles, we focus on empowering our clients to not only find the right person but to be the right partner. That’s what leads to lasting relationships.

Now, a year into the business, we’ve already seen incredible success—engagements, long-term relationships, and so many beautiful love stories that wouldn’t have happened if I hadn’t taken the leap. Looking back, I’m so grateful I trusted my instincts and followed my passion. Building this business wasn’t just about launching a matchmaking service—it was about creating something meaningful for the people in my city.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I originally started my career as a school psychologist, a field that allowed me to understand human behavior, relationships, and personal growth. While I enjoyed my work, I knew I hadn’t yet found my true passion which led me to exploring other ways to use my psychology background.

During that time, I had this extra creative energy, and matchmaking became something I did naturally. I started setting up friends and colleagues and made my first successful matches. Seeing those connections form brought me so much joy, even though I never imagined it could become a career.

Then, one night at a basketball game, I met a professional matchmaker. She also had a psychology background, and I spent the whole game picking her brain. That conversation was the lightbulb moment for me. I realized matchmaking was a real profession—one that aligned perfectly with my skills and passions. By early 2019, I had officially entered the matchmaking industry. I quickly became the top recruiting matchmaker at the country’s largest matchmaking firm and ultimately moved into a leadership role. After 5 years, I was ready to start my own company in order to serve my local community.

Now, I’m the founder of Dara Rae Matchmaking, a boutique executive matchmaking firm serving Philadelphia and the greater Philadelphia area. We specialize in helping accomplished professionals who are seeking a meaningful connection—most often leading to marriage. Our clients don’t want to rely on dating apps, which have become increasingly frustrating and impersonal, and they’re not meeting potential matches in their day-to-day lives. They certainly don’t want to mix and mingle with employees or colleagues.

That’s where we come in. Unlike dating apps that focus on endless swiping, we prioritize quality over quantity. We thoroughly vet every match, ensuring they align with our client’s values, lifestyle, and relationship goals. Our process is intuitive, personalized, and strategic—we don’t just match based on data points; we match based on human connection. And to make things even easier, we plan the dates, ensuring a seamless experience that saves our clients time while increasing their chances of finding the right person. Our success rate is significantly higher than dating apps, and at a time when loneliness is at an all-time high, we’re helping people build real, lasting relationships.

Beyond matchmaking, we also offer strategic dating guidance to help our clients navigate relationships with confidence. Additionally, we host monthly singles events, creating a vibrant, welcoming community where people can meet organically.

What I’m most proud of is the deep dedication we have to our clients—not just in finding them matches, but in truly understanding them and supporting their journey. And, of course, I’m proud of the relationships that are formed because of our work. There’s no better feeling than getting that text or phone call from a client saying, We made it official!

For anyone who wants to follow along with our Philadelphia matchmaking and dating adventures, you can find us on Instagram @DaraRaeMatchmaking.

Can you open up about how you funded your business?

That’s an interesting question. I was fortunate that the stars sort of aligned when it came to funding my business. I was working for a matchmaking company at the time and had been thinking carefully about when the right moment would be to resign and start my own firm. Financially, I knew I needed some initial capital to get things off the ground—setting up my business legally, building a website, investing in software, and handling other startup costs.

Then, almost serendipitously, a contact of mine reached out and asked if I could be his matchmaker. He was ready to invest in finding the right partner and trusted me to guide him through the process. The fee he paid became the exact funding I needed to officially launch Dara Rae Matchmaking.

That moment meant so much to me—not just because it provided the financial push to start my business, but because it was a sign that people truly valued my expertise and trusted me with something as important as their love lives. I’m forever grateful for that first client who believed in me, and in a way, he was the catalyst for everything that has followed.

Any insights you can share with us about how you built up your social media presence?

While I wouldn’t call myself an influencer, I have built large and highly engaged communities online—especially on Facebook. One of my most successful communities is Date Him Philly, a Facebook group with about 22,000 single women in Philadelphia.

The idea for the group came from noticing a trend in local Facebook communities—women were sharing warnings about men they had bad experiences with. While those conversations were valid, I found myself asking, Where are the good men? Why aren’t we talking about the ones who are great partners? So I created a space where women could showcase and vouch for quality men in the city (with consent, of course), and it naturally evolved into a matchmaking-style community.

The response was overwhelming. Women started inviting their friends, the media picked up on the concept, and before I knew it, the group was thriving. The best part? It’s led to real love stories. I’m actually attending our first Date Him Philly wedding this summer, and so far, we’ve celebrated three engagements that started in the group. Seeing those connections form was one of the many inspirations behind starting my own matchmaking business.

The success of Date Him Philly even inspired us to launch a men’s group for the same purpose. Through it all, the key to growing an audience has been staying true to the why behind the community. My biggest advice to anyone looking to build a social media presence is to focus on the value you’re bringing to your audience. Whether it’s creating a space for support, education, or connection, if you solve a real problem and stay committed to your mission, people will naturally gravitate toward it, and your community will grow.

Contact Info:

• Website: https://www.dararaematchmaking.com
• Instagram: https://www.instagram.com/dararaematchmaking/
• Facebook: https://www.facebook.com/profile.php?id=61565456172841#
• Linkedin: https://www.linkedin.com/in/dara-rahill-ab549967

Image Credits

Melissa Joy Photography