Friends don't let friends start a romance at Starbucks, and other secrets of an elite matchmaker

In search of a better way to cultivate a thriving relationship, I stumbled into the matchmaking business

Published March 22, 2019 7:00PM (EDT)

 (AP/Ted S. Warren)
(AP/Ted S. Warren)

In 2005 when my first marriage wasn’t working, we had two choices: religious-based counseling or marriage therapy. We had tried the therapy route. Through that process, it became clear to me that what you spend your time dwelling on — in our case, the problems in our marriage — is what ends up growing.

One day, my then-husband declared in our shared office, with clients in the building, “This isn’t working for me and it looks like it’s not working for you either. So why don’t you just disentangle yourself from my life?” He proceeded to walk across the room and demand I shake on the fact that we were commencing separation, nine years into our relationship. The puzzle to rekindle our love was no longer in my hands to solve.

That was one of the big curveballs of my life. But it gave me the idea to start a new business focused on optimizing romance rather than diagnosing problems. I became passionate about figuring out what makes us tick in our interpersonal relationships and fascinated by the new veins of scientific research on love and relationships. I went to New York City to attend the Matchmaking and Behavioral Sciences Institute and became a Certified Matchmaker, and returned to my alma mater to write my business plan while getting my MBA in entrepreneurship. Meanwhile, I traveled around the nation to learn from my favorite authors, coaches and scientists.

Through my studies, I discovered core patterns that affect how people act and react in partnership: each individual’s top relationship patterns weave a unique fabric of who they are as a partner. I began teaching, writing and coaching others how to better understand themselves and how to guide someone new to be in partnership with them while shedding light on the ways their patterns wove together. I provided those who were single with the tools to choose wisely while they dated. And I shared both practical wisdom and science-backed advice on how to pave the road to a thriving relationship from square one of a new union.

Two years into this journey, people who had been attending my classes, events and coaching began to ask if I would help them find someone special. I had reservations about jumping into the business of matchmaking — I had heard about a lot of unethical practices from close acquaintances who had worked for established matchmaking and dating services. Plus, so much of the business targeted high net-worth men exclusively, and that didn’t resonate with me — nor did the slick ads in the back of in-flight magazines and the Robb Report.

But at that point, matchmaking was moving beyond the yentas; it was on the threshold of becoming mainstream. “Confessions of a Matchmaker,” debuted on TV in 2007, followed by Bravo’s “The Millionaire Matchmaker” in 2008.

“It’s not as taboo to have a matchmaker as it was when I first began,” Mandy Watson of Elite Private Search, who’s been in the business since 2000, told me recently. “Overall, I feel online dating sites and apps have influenced more people to work with matchmakers because they find it saves them precious time while providing more peace of mind.”

From being on the fringe of the industry through my CMM certification, I knew a few ethical matchmakers who then became my mentors and friends. Sharing notes and best practices with them helped me lay the foundation for my own matchmaking business. By the beginning of 2010, clients had begun to trickle in. But it took a bizarre stroke of bad luck for my matchmaking services to really take off.

Finding Love in Hell

I was building a new business, but for a romance and dating expert, my own personal life was, ironically enough, falling apart. I thought I was getting married again, but my engagement of less than a year ended, and my ex-fiancé refused for months to leave the loft we shared until the lease was up. I suspected he had been having an affair, and he finally admitted to it — in a Facebook post — the day after he moved out. The very next day while sitting in traffic a car hit me at 45 miles per hour, which gave me a concussion, whiplash and nerve damage that caused facial and tongue numbness. The day after that, I had a cervical biopsy which came back positive. And within a month of the accident and a dozen migraines later, doctors discovered a brain tumor. All of this taught me to never say, “It can’t get any worse.”

It also taught me who my real friends are. So many amazing and supportive people, including a friend who is now my life partner, rallied to my side. After my ten-hour brain surgery, these wonderful friends hosted a fundraiser to help with my medical and living expenses. At that party, people from all of my prior careers, interests and communities converged. The caliber and diversity of the group served as a testimony to the quality of my network, and a number of them sought my matchmaking help as a result. Clearly, I knew some incredible people.

By the time I’d fully recovered in 2011, I moved in with my partner, and by 2012 we had a beautiful baby boy. Over the next several years, I consistently worked with a full roster of matchmaking clients. From what I’ve seen, a majority of new matchmakers don’t last more than two to three years. I think many believe it’s going to be far easier than it actually is to sustain as a business.

“People think it’s a sexy job, when in actuality it’s not. It’s a brutal career path filled with uncomfortable conversations and a tough sales process,” says Erica Arrechea, co-founder and lead matchmaker at Cinqe Matchmaking. “People come in and out quickly and thus can leave the singles who worked with them with a bad taste in their mouth. People need to vet their potential matchmaker completely and know that no two matchmakers are alike.”

Some companies received so many bad Yelp reviews they had to close their doors, but quickly re-opened under another name. They were money-makers, not matchmakers. I didn’t want to be part of that. I wanted to be an agent of love.

A secret society of elite matchmakers is born

In 2018, a few of my likeminded colleagues decided to form our own secret society of integrity-based matchmakers. Once every six weeks, in one of the most opulent private social clubs in San Francisco, our group of eight to 10 matchmakers meet, laptops open, to collaborate on finding love for our clients.

To join our group, you need to be recommended and pre-screened by one of us. Is this a person who keeps their word to friends, colleagues and clients? You can hear, feel and witness if an individual is operating from a base of integrity.

Another quality we evaluate on is intuition. They should feel and see things that the general population probably doesn’t. We are looking for someone who has honed their intuitive people skills. We rely on their ability to accurately gauge the type of person they are referring to us. If we accidentally set a client up with someone's referral who turns out not to be who they were reported to be then our own credibility is on the line.

This might sound obvious, but it has to be evident that they truly like their clients and want the best for them. They place their clients’ interests as a top priority. When they are outside of their home, they are always looking for potential matches; it’s just a part of who they are and the lens they use to see the people around them.

And finally, we look for a combination of emotional intelligence, street smarts, knowledge of their profession and overall intellect. I find people attract people who are similar to themselves. So if a matchmaker has a high level of intelligence, they’re more likely to have a solid foundation of individuals — in their communities, databases and beyond — who are equally perceptive.

As a relationship expert and matchmaker, I’ve enjoyed having these women as a consistent resource over the past year. At a typical meeting, I’ll share a photo on my screen with the group and explain the challenge in front of me. “I have a fabulous guy in Campbell. 6’4”, Jewish, grew up in the Bronx, successful entrepreneur with two grown kids, very creative, authored two sci-fi romance novels. He’s looking for a 40- to 50-year old, co-adventurer, prefers tall, that she has kids and physical touch is one of her top love languages. Any thoughts?”

You can almost see the mental rolodexes of these highly networked matchmakers scrolling through the images in their minds and then moving to their laptops as they look up the women they know who may fit that description. We exchange dozens of leads over the course of a few hours, using personal databases, LinkedIn and Facebook to come up with potential matches for each matchmaker’s clients.

Why Don’t Clients Just Swipe For Themselves?

“We work with a lot of busy professional men who don’t want to be seen on an online dating site or app,” says Arrechea. “Beyond preferring a confidential way to meet someone special, they have no desire to weed through the thousands of women online only to get flaked on or find out the woman is not a fit at all. The work and disappointment simply doesn’t appeal to them. They have better things to do with their time.”

And just because online dating is easy doesn’t mean everyone’s good at it, or enjoys the wealth of options available at their fingertips.

“There is a fatigue occurring with the whole swipe culture,” says Siobhan Copland, matchmaker, coach and founder of the UK-based Cupid in the City. “It’s exhausting and can impact an individuals’ confidence, as more face continued rejection and ghosting. There’s a lot less manners in the way people deal with people they meet online. And I find people often hide their true self.”

How I Make a Match

Those initial first hits are just the beginning. Over the following days and weeks, I set up calls and meetings with the leads I’ve received to screen potential matches for my client. I’m looking for at least a 75 percent match on both my client’s and the potential match’s wish lists before I move forward with an introduction.

My vetting process is involved and longer than most, because I want to match as many key relationship patterns as possible. I begin with a phone interview and at the end of the call, if they still sound like they could be a good match, I ask them to fill out a detailed questionnaire and take two personality quizzes online. Next, we schedule a call to analyze their results and to assess if they are indeed in alignment with my client’s ideal partner.

My client is then notified, and if they agree it sounds like a potential match, I arrange their first introduction over a cup of coffee or tea, or a glass of something. It’s their preference, but I guide them to make this first point of connection meaningful and memorable. I have one rule about this introduction: “Friends don’t let friends start their love story at Starbucks.” Make it special from the first glance.

Once all the details are set, I’m on call during the time leading up to their meeting, either for quick pep talks or to let a party know if someone is running a little late. Prior to the introduction, the client and the match don’t exchange phone numbers, email addresses or photos. Once both parties have contacted me and let me know they have a desire to kiss the other — that means there’s chemistry — I share their contact information and nudge the gentleman, if he’s matched with a woman, to make the first move. The rest is up to them, though in my matchmaking circles, aftercare is also part of the package.

“My clients find that the true value comes after they have found someone special and are in the beginning stages of dating. When you have a professional matchmaker who is established, has an education in psychology, who is intuitive and cares about their clients’ overall happiness, it’s invaluable,” says Sameera Sullivan, founder and CEO of Lasting Connections. “One of the biggest added benefits is having someone, outside your friends and family, guide you through the ‘how to be in a relationship’ initial steps which ends in a successful budding relationship.”

Looking back now, I see my week from hell as a blessing in disguise. If my cheating ex-fiancé hadn’t left me, I would never have found the love of my life, nor had our son. If not for the car accident, the doctors wouldn’t have spotted my tumor. And if not for all of that and the support of my friends and family, I probably never would have made it through that crazy-hard time keeping my business afloat.  I’m blessed and delighted to continue to do such meaningful and fulfilling work as helping people find and maintain love, too.

Thinking about hiring a matchmaker? Ask these questions first

  1. Are you a certified matchmaker? Truth is almost anyone can become a matchmaker, and even certified matchmakers (CMM) don’t always follow ethical practices. But at a minimum, if you are paying someone to find you a match, make sure they are certified.
  2. Can you give me 2-3 references I can check?A reputable matchmaker should be happy to connect you to happy clients. If they can’t, you should say thanks but no thanks. These references will be the truest measure of what your matchmaker is like to work with. Be careful, though; a disreputable company could pay people to pretend to be happy customers.
  3. How will you find my matches?If they evade this question, it could be a red flag. Are they going on Tinder on your behalf? If you are working with them because you want confidentiality, make sure they’re not using your image online to find you potential matches. If after meeting a match they are nowhere in the ballpark of what you have explained you are looking for, do you still have to pay?
  4. How do you weed out the crazies?Do they interview your potential dates in person or by phone prior to matching you? Do they conduct background checks? Are these individual referred by trusted sources?


  1. How long have you been a matchmaker?What makes you different from the rest? What makes you passionate about matchmaking? Look for someone who feels this is his or her calling.


By Joy Nordenstrom

Joy Nordenstrom is a relationship expert, certified matchmaker, special event planner, writer and founder of Joy of Romance, Inc. She’s often cooking or baking for her partner and their son. She plans to share her recipes on her new blog,

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