To Fall in Love with Your (Boss) Self, Do This

On Sunday mornings, after retrieving The New York Times from the driveway, I used to turn first to one section: Modern Love. This was ironic, considering my track record. An engagement shattered by cheating—with a neighbor.A marriage dissolved under the weight of emotional distance and drinking.A child with a man whose work always came first. I had fallen…

On Sunday mornings, after retrieving The New York Times from the driveway, I used to turn first to one section: Modern Love.

This was ironic, considering my track record.

An engagement shattered by cheating—with a neighbor.
A marriage dissolved under the weight of emotional distance and drinking.
A child with a man whose work always came first.

I had fallen hard and repeatedly for distant, self-obsessed men. Outwardly, I was cynical. Inwardly, I still believed in love enough to read about it every week.

One essay lodged itself in my mind and refused to leave: To Fall in Love with Anyone, Do This by Mandy Len Catron. It described a study in which scientists helped strangers fall in love by asking each other thirty-six increasingly intimate questions.

Would you like to be famous? In what way?
What would constitute a perfect day for you?
Do you have a secret hunch about how you will die?

After answering the questions and holding prolonged eye contact, participants often reported falling in love.

At the time, the piece deepened my bitterness. I had never met anyone who wanted to know me deeply enough to sit across from me and work through such an inventory. The questions felt like proof of my unworthiness.

How could I be interesting if no one was interested?

And then, in the thick of my self-pity, a realization landed with force:

I didn’t even know how to answer the questions myself.

The Radical Act of Turning the Questions Inward

The first question alone paralyzed me:

Given the choice of anyone in the world, whom would you want as a dinner guest?

I froze.

Not because no one wanted to know my answer.
But because I had no idea what it was.

I hadn’t been interested enough to get to know myself since my teenage poetry-writing years. I had built entire relationships around studying other people—what they wanted, how they felt, how to please them—while remaining largely unfamiliar with the woman in the mirror.

So I bought a composition notebook.

I wrote out all thirty-six questions.

And I began.

I couldn’t answer more than one at a time. The excavation was exhausting. Sometimes it took hours to uncover a single honest response. Old hurts I’d politely ignored in therapy churned my stomach. I hated it.

But I kept going.

It took over a month.

By the end, I felt illuminated. As if I had finally, lavishly, powerfully, stared myself in the eye. The questions became less about falling in love with another person and more about falling in love with the self I had abandoned.

Loving myself had always sounded simple. But after multiple abandonments, the concept felt like a puzzle missing its edge pieces.

The questions helped me find them.

When I finished, I bought more composition books and copied the questions into each one, sending them to my brilliant, fierce female friends—the ones who also loved men who didn’t appreciate them.

One question in particular lingered:

Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

Healing in the Quiet

I pushed forward in my life—lonely, yes, but steady. I focused on my daughter. On building a small, warm home. On becoming the best version of myself.

For years in therapy, I had avoided talking about myself—my past, my parents, my wounds. It made me uncomfortable. I wanted to move forward, not dig back.

But I was stuck because I was avoiding myself.

The questions opened the door to healing. As I focused inward, something softened. Love began to bloom in the small life I was building with my daughter.

Then came the pandemic.

As a natural introvert, I didn’t mind working from home. But during that time, I began conversing more with my boss.

We had always been friendly. Before 2020, we shared office space, though he traveled constantly. He was mid-forties, tall, blond, irreverent, full of corny jokes and a sharp mind that untangled complex problems with ease. Divorced, with two artistic daughters our children adored.

There had been the occasional harmless fantasy—a dirty dream that made the office morning awkward—but it was always contained. Manageable.

Until travel stopped.

He brought bacon-wrapped figs to my driveway. Then cookies. I found excuses to drop by his house, too. We messaged. We emailed. We shared fiction drafts and poems. We drifted into family histories and disastrous relationships.

I fell in love.

It felt ridiculous. Unrealistic. I wanted to tell him, to be honest about my crush so he could shoot me down and we could return to normal life—the one where I’m not fantasizing about my boss.

Instead, I kept writing back. I didn’t want to lose what we had. I looked forward to his emails. I lit up when he messaged me and read them over and over.

And one day, while crafting a careful reply to one of his long, probing emails, I realized something startling:

We had been doing the questions.

What did ten-year-old Amy struggle with?
What did she dream of?
What would she tell you now?
What would you tell her?

Without intention, our emails had become soul-baring exercises in vulnerability.

The Illusion of Destiny

In December 2020, I went to his house to drop off materials. After dark, we stood on his porch watching Great Conjunction of Jupiter and Saturn—the so-called “Christmas Star.” The planets appeared to touch, though they were still hundreds of millions of miles apart.

That night, I told him I was in love with him.

To my shock, he said he felt the same.

It felt cosmic. Meant to be. As if the universe had aligned us and all that remained was to thoughtfully dismantle the obstacles.

We informed HR. We told the company.

A few weeks later, he ended it in an email.

Restrictions eased. He began traveling the world. I imagined beautiful women in exotic locations listening to the same promises. I stayed behind—professional on Zoom, undone afterward.

How could something that felt so destined dissolve so easily?

I walked each morning on a wooded path we once shared, rehearsing fantasies of reconciliation—if only to avoid admitting to others that it had failed.

Then one day, looking through the pines at a quiet stream held back by a beaver’s dam, I realized something:

I wasn’t walking there to meet him.

I was walking there to meet myself.

The planets we watched weren’t stars. They were massive bodies continuing in their own orbits, reflecting light because that is what they are meant to do.

They crossed paths briefly.

Then they kept moving.

So was I.