Week 41: Matchmaking II

Week 41: Matchmaking II

My 2018 has been all about exploration: trying all kinds of new things, both to overcome my hesitations, as well as to find my joy and purpose(s) in life. In this spirit, I applied for and started a matchmaking position several months ago. In my post last week, I shared some thoughts about it.


  • I love that my clients proactively seek what they’re looking for in life

  • Relationships with others are born from a relationship with the self

  • Although matchmaking is a purpose-driven profession, it’s far from my own purpose

  • Matchmaking is a great detachment practice

Well friends, let the thoughts 5-9 flow forth…

Thought #5: Age comes fast. Even the many clients who don’t want children say things like, “Where did my life go?“ or “I feel so sad that I didn’t focus on relationships until my 40s“ or “I didn’t expect to be this old and not have a partner.“ Add the pressure to have kids into the mix, and it becomes all the more sensitive.

If relationships aren’t an interest, something else is. Whatever it is, cultivate it.

Live that life. Ask for everything, run the marathon, take the class, invest in relationships. We DON’T have a lot of time here. The face in the mirror — suddenly, it seems — becomes much older than its owner feels. Days crawl by, and we forget that years speed by. Do the damn thing.


Thought #6: Matchmaking has given me some insight into how much we humans love shortcuts. And no — I’m not talking about delegating or outsourcing the dating process.

I’m talking about wanting the unearned. Desiring good body without working out. Wanting a fairytale relationship without learning the skills it takes. Plagiarizing a paper to get a good grade.

We, as animals, are hardwired to like shortcuts. Expending the least amount of energy to succeed is, after all, a survival skill and a biological drive.

However, if our hearts yearn for something…there is nothing more rewarding than putting in the work.

Eventually, the work becomes the reward. And the result, if it comes, is just icing on that cake.

When I began matchmaking, I thought my clients needed a reality check that began with a therapist. I still do think many of them should be seeing healers instead of matchmakers, but a reality check is unrealistic.

Or rather — a reality check that dawns one fine day is unrealistic. Who just ‘wakes up and smells the coffee’? No one. Instead, putting in work is a reality check that works.

When someone invests in themselves the work it takes to become the kind of person they want to date…they become so much more dateable.

When we put in effort, the effort eventually makes the effort for us, and in time ‘effortless effort’ takes hold. There is no placeholder for work.

Thought #7: Speaking of reality checks…when I applied for my matchmaking job, it seemed glamorous. It’s not. It’s really hard.

And speaking of effort…between finding matches, managing client expectations, dealing with schedules, and talking to people all the time, it’s a lot of hustling.

Potential matches don’t call back. Clients are often so nervous about handing off their love lifes, they give me all kinds of requirements. People lie about their incomes and their heights. People ghost on date night.

It’s enticing to romanticize what we see from a distance. Approach anything really beautiful, truly great, and we will see that its creation process may not have been a smooth ride.

Glamour is often a façade, and if it’s not, the fabric of its beauty is in the grind. And the grind is tolerable when the larger purpose is a passion, or a calling.


Thought #8: But if something is not a calling, why struggle to make it work?

To clarify: I know I said work is rewarding, and it is. We have so much internal work to do, and external work is wonderful, if tough, when it’s aligned with our natures. If a body loves to run, let us put in the work to run a marathon. But twisting work out of our bodies, punishing ourselves with it, or weaponizing it as a ‘should’ are true soul-killers.

We live in a culture that glorifies struggle. If you sacrifice yourself, that’s ‘good.‘

But struggle and work don’t need to equate. Work is a patient plodding along, keeping the goal in mind, but it can still unfold with ease. Living can unfold with grace — in fact, the very essence of ‘effortless effort’ means putting in patient effort while in conversation with the river of life. It is an ebb and flow, not a charge. Ease and work can integrate to form a meaningful life.

The people who say aren’t where they want to be are often not there not because of inaction, but because they were derailed by the wishes of others.

In a larger context, my point is to not let societal expectations dictate so much. Yes, do the thing. Get after action. But only if it speaks to your heart.

Thought #9: Chemistry is overrated.

Sometimes clients dismiss a first date, saying something like “there was no chemistry.” If people want a spark on the first date, they want a spark on the first date, so I usually don’t push it, but…

Connection can develop.

A relationship is all about how someone shows up for you. How someone gives to you, and receives from you..

I do think chemistry is vital. A contained fire is nurturing, igniting, life-giving. An uncontained fire is devastating. Without the foundation of a good relationship, chemistry can become a conflagration.

But it can be cultivated in time if the foundation for it is there. It’s something, not everything.

After this matchmaker undertaking, I think I could partially empathize with Santa if he were real. For many people approach “Matchmaker, matchmaker…” in the same way they do “Dear Santa.”

At the same time, matching has given me invaluable opportunity to practice not taking on the burden of expectations clients have — expectations that, even as I employ to find possible fits, are essentially their own to work through.

Many of my clients are realistic, have invested in matchmaking for the right reasons, are fulfilled within themselves, lead enriching lives, and simply find dating apps inconvenient (amen).

Their ability to say yes to actualizing what they want is inspiring, and while I’m not planning to continue this journey for more than 6 months, I hope to help them find what they are looking for.

And eventually, I think I will find my purpose in being some kind of fire-lighter…I’m simply just not a matchmaker.

Week 42: Goodbye to Grandma

Week 42: Goodbye to Grandma

Week 40: Matchmaking I

Week 40: Matchmaking I