The Leads Learn Their Lesson, Part One
“Desire for a relationship is not the same as readiness.” My colleague Carina’s words echoed in my head,
and I wondered whether the same reasoning could apply to any aspiration. It was May 2021, and my body
had rejected the remaining embryo at our original IVF clinic. (Even though we had healthy embryos
waiting for us at the new clinic, I couldn’t bear the thought of leaving another behind. Now, I’d have no
choice.) What is wrong with me? I wondered as I got my blood drawn for the umpteenth time. I’d tried all
the scientifically debunked superstitions that the doctor and her referrals had recommended: an injection of
soya bean oil, egg yolk, and glycerin to prime my body; ingestion of gross herbal teas on the daily; legs in
the air for twenty minutes following the transfer; and acupuncture the day of. Still, no amount of
intervention had empowered my body to do exactly what I needed and wanted it to do most. I felt defeated,
and I thought about how applicable Carina’s words were not only to my life but also to the lives of those I
coached. When we started working together, Kent, Meera, and Callie craved the same universal,
intangible, equal parts frustrating and fulfilling thing we call “love,” and yet—at least some of the
time—seemed to actively undermine their very chances at attaining it. But were they more ready to attract
it now? Kent appeared to be falling harder for Rita, evidenced by his unsolicited weekly updates to me
over email. (“I did it. I think I finally won over her cat.”) Since moving on from Trevor and having the
clarity to truly unpack their
dynamic, Meera seemed to decide that being treated well, consistently, was finally a turn-on for her—and
while she was still sk eptical of someone less passionate up front, she agreed it was no longer a dealbreaker.
Even Callie reaffirmed her commitment to ke eping an open mind on her search. “You really think I could
meet someone playing pickleball?” she asked me earnestly, a month shy of her yearlong membership
expiring. I responded encouragingly, and also recommended she try hiking groups, concerts, and dining
meetups as well. If she connected with someone during any of those activities, she would know from the
start that they had something in common (hardly a requirement but it certainly couldn’t hurt). It also
wouldn’t be a wasted evening if she didn’t meet anyone, because she’d already be partaking in an activity
she enjoyed. I also suggested she consider hobbies or interests her future partner might like, even if they
differed from her own. “You might not be into sports, for example, but what if your future partner loved it?
Would it really kill you to grab a drink at a sports bar one night with your friends instead of your usual
wine bar?” Similarly, men often overlook the power of showing up to a workout class typically populated
by women (think yoga or exercise dance). While I recommend they wait until after class to strike up
conversation with someone (most people prefer to focus on their workouts), this is another way someone
can expand the circle of singles they’re typically exposed to. Even if a woman you approach is “taken,”
your confident and adventurous spirit might inspire them to think of their single best friend they now want
to introduce you to. When it comes to dating in real life (IRL), which is rising in popularity again due to
the decline of online dating and other factors, the possibilities are endless. Naturally there are bars, friends’
birthday parties, singles mixers, and fun classes from pottery to stand-up comedy typically available. (I
also encourage all my male clients to try speed dating, because those events are typically crawling with
incredible women, while the quality of men there tends to be more suspect.) But if all else fails, you can
always get creative. Dave Cline, a twenty-eightyear-old data manager from West Philly, once spent a
thousand dollars to rent a billboard in his neighborhood, asking women for dates. Hunter Lineberry in
North Florida started following Chat GPT’s suggestions of what he should do to
find a wife, and posted the results on Tik Tok. Karolina Geits, a model and influencer, went viral for
walking the streets of New York with her “looking for a husband” sign. And in a trend that gained
popularity in 2022, read-only “dateme docs” became a long-form way to advertise who you are and what
you’re looking for in a partner. The dating CV is a nod to personal ads that used to get placed in
newspapers—some look like dense résumés, filled with nothing but facts, while others sport sleek designs
and look more like polished websites, even equipped with musical soundtracks. Callie wasn’t ready to try
anything less traditional yet, but feeling inspired by our p ep talk, she started averaging about six dates per
week in a determined, lastminute frenzy; Meera, though, needed more nudging in this area. She was
relatively more reserved to begin with, and less likely to walk up to attractive strangers and initiate
conversation. She also felt differently about her finances than Callie, and believed that while free “outings”
such as farmers markets or volunteer opportunities were worthwhile, memberships and paid activities at
social clubs such as Soho House or Singles Only Social Club (SOSO) weren’t a good use of her income.
(If you do have the discretionary funds, though, I highly recommend it!) And let’s face it: some events are
worth splurging on. My good friend Danene attended my destination wedding despite not being in the best
position to do so at the time. She even roomed with someone she didn’t know well in order to make the trip
more affordable. The result? She wound up meeting her husband that weekend, Dave’s good friend Jay!
That five hundred dollars ended up being well worth it. Meera had an additional obstacle, though, at least
in her eyes: her closest friends were all coupled up, and she felt uncomfortable attending any outings solo.
My first st ep was convincing her to do it anyway. Even if she didn’t wind up meeting anyone, simply
st epping outside her apartment could yield other valuable benefits. Was she being more active than usual?
Getting sunshine she might not ordinarily receive? Could she acquire a new skill? Or meet a new friend?
“Statistically, it’s actually better going out alone,” I pointed out the silver lining to her. When alone,
women appear more approachable to men than when they’re with their girlfriends. It takes someone
extremely confident to walk up to
your group of friends and strike up a conversation with you, whereas it’s less intimidating if you’re out by
yourself. While having a partner who’s confident in any situation would be great, your future husband
might just be the kind of guy who would be more likely to walk up to you if you weren’t surrounded by a
sea of other women, analyzing his every move. I stressed to Meera the importance of initiating
conversation, and not to assume a guy wasn’t right for her simply because he wasn’t approaching her. This
was apparent to me after all the men I’d coached, but not to Meera, who was self-conscious to begin with.
She was more the type to attend an event and stand around uncomfortably, waiting for men to magically
notice her. While that’s fun to fantasize about, men don’t approach women as much as they used to. In the
age of swiping culture, with endless options at our fingertips, why risk possible face-to-face rejection?
What’s more, “in the wild,” it can be hard to tell whether the person you have your eye on is even single.
“I’m not suggesting you go up to a guy and assert, ‘Hey, you’re cute. What’s your phone number?’” I
explained to Meera. “I’m saying if you’re at the grocery store, maybe you go up to him and ask if he
knows where the pasta sauce can be found.” “And then what?” she wanted to know. If he was interested in
getting to know her better, I told her, he’d do the rest. He’d bring her to the pasta aisle himself, or turn it
into a conversation. If he had a girlfriend or wife back home, or simply wasn’t interested in her, he’d say
he didn’t know, or point her in the right direction and leave it at that. Approaching someone takes
confidence, and confidence is attractive—so at the very least, he’d respect the move. “Just because you
strike up conversation with him first doesn’t mean he can’t ask you out first,” I highlighted. There are no
hard rules when it comes to this stuff. Talking to a guy doesn’t mean you’re automatically flirting with
him— he’ll only read into your interaction if he wants to. Meera was open to trying this, but for some of
my clients, that’s a st ep too far. For them, I recommend starting with approaching people they have no
romantic interest in, to remove the stakes. For some, there can be a feeling of shame that comes along with
being single, or a feeling of insecurity as they move
through the world with this self-imposed label—as if their relationship status is as visible to others as their
shirt. For them, kicking off a conversation with someone they’re interested in can feel daunting. My client
Teresa fell into this category. She was a widow who hadn’t so much as flirted with a man other than her
husband in forty years. By approaching women first, she was able to get in some conversational practice
without the fear of consequence. Once she mastered that, she could feel more comfortable approaching
men. “So you understand your ‘homework’ then?” I playfully asked Meera, who nodded. “Yup. Stop being
afraid of the hot Starbucks barista?” I laughed. If she could only channel the same confidence and humor
she had with me, there’d be no looking back.