Building Character
I closed my eyes in yoga class, trying to put the Kent business out of my mind. While it doesn’t always
seem this way to our clients, matchmakers have insecurities too. When a date goes wrong, when I peg
someone incorrectly, or when a client vanishes, it’s hard not to question my instincts. Despite the good
handful of marriages, engagements, and babies I’d helped create, I started to wonder whether I really
possessed the qualities needed to take my skills to the next level. Perc eptiveness, humility, flexibility,
empathy, and confidence were all essential to serving my clients best, but right now, I was questioning if I
had the right balance of any of it. Anyone can pick up on cues about someone’s personality and
preferences, but to be perc eptive, a matchmaker has to detect less obvious traits and truths. For example, if
a man says he’s looking for someone “active,” he might be referring to a partner’s look more than their
lifestyle. Or similarly, if he says “personality is more important,” but then sends you photos of
flawless-looking models he swipes right on, your first match for him better be a looker if you want him to
“trust” you. Men often sugarcoat their preferences—especially the more superficial ones—to me and my
business partner, believing that because
we’re women, we might get offended otherwise. They also tend to censor feedback following their dates if
they detect the other person isn’t interested in them back, self-conscious about showing their cards. If we
couldn’t read between the blurred lines, we’d be less effective at our jobs. Men aren’t the only daters who
aren’t always candid, though. For example, if a woman says she’s open to all socioeconomic classes but
flies private and drives a Ferrari, she might be trying to avoid judgment and, in fact, prefers someone more
financially comfortable. I’d always thought I was perc eptive, but I also thought Kent and I had a good
rapport—one that would make it difficult for him to so casually disappear on me. I was wrong. Next I
thought about humility. If you’re a matchmaker or dating coach looking for credit every time you
accurately make a prediction—positive or otherwise—you’re in the wrong profession. I can recall several
times I’d pitched a joke in TV writers’ rooms that was glossed over, only for another writer to pitch an
identical one moments later and for it to be well received. This used to infuriate me. But when it comes to
helping people on their journeys to find love, you have to remove ego from the equation. There’s also
humility in volved in recognizing that, given the right personality and dedication to the craft, anyone can do
what we do. While some claim to be “born” with the gift to connect people, most of what’s needed to
succeed in our profession is learned on the job. After all, predicting which singles will couple up well, for
the rest of their lives, is a skill that can only be sharpened by failure and experience. As I listened to the
singing bowls and soothing nature sounds on the class’s soundtrack, I thought about clients who broke the
mold—such as my unscripted producer client who shared her preference for “pocket-size men,” or the data
scientist who actively sought women with pronounced jawlines. I’d also predicted the outcome of many
successful relationships, but had been surprised when certain singles didn’t hit it off, and tried my best to
learn from those interactions (such as an e-commerce CEO who only ordered water during our restaurant
meetup, but wowed his dates following a little coaching). Once I’d acc epted that my instincts weren’t
always right, I adopted more flexibility in my practice. Even in cases where my intuition is correct, clients
don’t always follow my advice. In the beginning, I talked dozens of daters into
going out with someone they weren’t originally open to, and it rarely led to success. If they had a fixed
notion of what package love would come in, I’d found it was best to try to deliver that first. After enough
strikeouts, they’d hopefully come around and let me take a less predictable swing (e. g., how I was able to
convince Kent to meet someone Natasha’s height). Still, that hadn’t been enough. “Desire for a
relationship is not the same as readiness,” my colleague Carina —whom I ran into at the matchmakers’
meetup—once wisely summarized the oft overlooked truth. Perhaps I was trying so hard to find Kent love
that I hadn’t stopped to question if he was ready for it. And maybe, just maybe, him taking a st ep back
from dating was in his best interests after all. Despite my attempts at remaining objective, I tend to get
sw ept up in the emotion of it all. I suppose this is where empathy comes in—a skilled matchmaker’s
double-edged sword. By being able to see the world from clients’ perspectives, I’m more easily able to
identify with their journeys, understand them, and find suitable partners as a result. (I’ve watched some
matchmakers operate who lack empathy, and these are often the same business owners guilty of treating
clients like numbers moving through their “system.”) But my empathy can sometimes cloud my ability to
think objectively. I can also be a harsh self-critic. Nearly two decades into the job, I still haven’t found a
way to s eparate clients’ joys and disappointments from my own. Their failures, or lapses in judgment, are
not my fault, I had to remind myself as I lay in savasana. For the last minute of class, I thought about the
final characteristic of what I believe makes a good matchmaker: confidence—the category I was most
wavering in today. The last time I remember feeling this way was when I initially contemplated the
coaching side of the business. Do I have enough knowledge and experience to fill multiple hour-long
sessions with clients? Who am I to advise them on their dating lives when my own love life is in shambles?
Only after Dave and I began dating did I feel ready. It turns out my confidence didn’t come from dating
him, though—but rather from the faith in myself that I was able, finally, to put my own advice into
practice. If Kent were to resurface, I decided I would shelve the women I planned to introduce him to—a
creative hairdresser, Cindy; an ind ependently wealthy
fitness instructor, Vanessa; and, most promising, an older and whip-smart financial advisor, Rita—until he
made more of an effort to work on himself. And in the meantime, I had other clients to focus on who
appreciated my help. “Slowly, begin to wiggle your fingers and toes,” the yogi before me commanded,
offering a gentle transition out of corpse pose. “And when you’re ready, please rise. Inhale your arms up
over your head, and exhale them down to your heart, in prayer. And remember: you are here to share, not
to be perfect.” He paused for a couple of breaths, and I smiled at the appropriateness of the mantra.
“Namaste.”
As I pr epped for a meeting with Lauren, I started to consider whether I was taking on too much. In addition
to running to doctors’ appointments, I’d been hired to write on a new animated series for Netflix, which
meant I’d have to book clients and coaching sessions around a soon-to-be-rigorous writing schedule. Our
matchmaking season was also ramping up significantly, with referrals flowing in due to pandemic-related
relationship issues. (Bumble even coined the term “New Dawn Dater” for anyone who’d recently ended
their longterm relationship.) The public’s interest in our industry also piqued after the premiere of Indian
Matchmaking on Netflix. The show wasn’t the first time matchmaking had captured the pop culture
imagination. Patti Stanger had risen to fame through her show Millionaire Matchmaker, which followed
her as she set up wealthy individuals searching for love; there was Darren Star’s Miss Match, starring
Alicia Silverstone, who had also played an amateur matchmaker as the lead in Clueless, an adaptation of
Jane Austen’s Emma (and a new iteration featuring Anya Taylor-Joy), and Hello, Dolly!. And lest we
forget, of course, the classic theatrical production of Fiddler on the Roof, Sarah Michelle Gellar’s character
in Cruel Intentions, and the matchmaker Kelsey Grammer pines for in the last season of Frasier.
Matchmaking was having a moment, and I was glad to be part of it.
I was also grateful Lauren was finally back from maternity leave. She could run point while I focused on
my other commitments, but she had a bit of catching up to do, including meeting some newer clients of
ours. They would be in great hands, but she agreed to ke ep me posted on any potential introductions before
they happened. As I glanced through our master list of clients, I provided re caps on where each stood on
their journeys. For the ones in newly formed relationships, we planned to check in and see how they were
doing. (I’d always hated to see a connection fall apart simply because one person forgot to stay in touch
with another while on vacation.) We also decided to preemptively reach out to people we hadn’t set up in a
while with updates. Like agents who submit their clients’ work for consideration often without their
knowledge, Lauren and I do a ton of behind-the-scenes work for clients that they’re unaware of. Updating
them regularly would be a full-time job itself, but I try to touch base once or twice throughout their
memberships to let them know we’re thinking about them and to help maintain confidence. Lauren asked if
I followed a client of ours, Mariel, on social media. I didn’t, so she excitedly shared with me that Mariel
just posted her first public photo on Instagram with a guy we set her up with a while back, Kenji. “I think
they’re official now!” I leaned over to take a look. Lauren had always been great at ke eping tabs on our
clients—even former ones—online. I had to laugh at the entire world finding out about their hard launch
the same time we did, but chances were they would drop us a personal note later that week. I also wanted
to fill Lauren in about recent setups: Heather, a celebrity assistant she and I matched previously, was now
going on a second date with a dynamic and femme literary agent I’d sent her way. Similarly, a new client,
Brandon, was going on his third date with Kate, the high-pitched hottie Kent had rejected. We also
discussed two new bachelorettes I hadn’t matched at all yet. When I activated the first’s membership, I’d
had several men in mind for her —but now one was unavailable due to a death in the family, and the other
had recently become exclusive with someone else he met on his own. So I needed to regroup. The other
bachelorette was also fantastic, but wildly different from the impression her intake questionnaire had
given. After talking it through, Lauren
and I landed where we always do: waiting for a new referral we were excited about rather than setting her
up with a subpar option. Quality over quantity, we reminded ourselves. Then, we shifted our conversation
to more challenging clients like Callie. I’d sent several frustrated emails about her to Lauren since she
signed up, and now Lauren wanted to know “how bad” Callie actually was. I shared that Callie was great,
but like many others who came before her, she’d been getting in her own way. “These people I’m
presenting to her are, objectively, amazing catches. Who knows—maybe you’ll have better luck.” “I think
you’ve been too nice,” Lauren told me matter-of-factly. “You should give it to her straight.” Lauren wasn’t
wrong. I’d been stewing, growing more and more impatient with Callie’s constant rejection of bachelors
and bachelorettes since we started working together, but k ept it all to myself. I’d been patient, trying to get
to the bottom of why she wasn’t rec eptive to any of my matches, but my patience wasn’t helping her. It
was time to give her some tough love.