The year was 2002, and the silence in my house no longer echoed—just hummed. My divorce had been finalized the day after 9/11. That fall, the world grieved—and I joined it, feeling everything and nothing all at once. We’d weathered a lot together—fertility issues, repeated relocations across the UK, my father’s long decline. Then came a transatlantic reboot with little support, as we tried to outrun a past we didn’t yet realize was catching up. In the end, what we carried cracked us open.
By winter, I wasn’t sure if I was ready to date again—or just desperate to feel something.
Friends had promised introductions. Each had someone in mind—a friend of a friend, a co-worker, a cousin. But when it came time to follow through, every prospect vanished. One had moved. One had married. One had come out. Another just stopped returning calls. It was like stepping onto a stage and realizing the rest of the cast had quit.
So I tried something new: Match.com.
Back then, online dating still felt vaguely illicit. People spoke of it the way they mentioned frozen embryos or offshore accounts. Amazon still only sold books. Most of us were still writing checks. But the internet was beginning to stretch its limbs. Why not look for love?
I filled out the questionnaire, uploaded a photo that was neither flattering nor dishonest, and waited.
My first match was K, a tenured psychology professor at the University of Pennsylvania. She was a few years younger, but not enough to feel strange. Our emails were fluid. She asked smart questions. Responded thoughtfully. It felt like something.
She suggested ice skating for our first date. I checked the rink’s hours, but she assured me it would be open. When we got there, though, the gates were locked. It turned out she’d simply felt it should be open.
We walked. It was bitterly cold—the kind that climbs through your sleeves and settles in your spine. She didn’t seem to notice.
She apologized with a shrug and suggested we try again the next night.
Part of me—an increasingly louder part—was screaming run away. But another part, quieter and more afraid, whispered that if I bailed now, I might not try again. So I said yes.
As we wandered, she shared her “partner selection process.” Her term, not mine. She’d started with 2500 men within 25 miles of the university. Narrowed it by age: no more than ten years older. That left 225. Then came education—must have a Master’s or PhD. That brought it to 27.
“I have an MBA,” I offered.
“Of course you do,” she said. “Or you wouldn’t be here.”
I smiled. “I feel honored to have made the top of your list.”
She blinked. “You’re number eight.”
“Did you meet the other seven?”
“Yes,” she said. “They were not suitable.”
She wasn’t being cruel—just clinical. As if I were the eighth résumé on a shortlist. It wasn’t unkind, exactly. It was logical. And after everything I’d been through, I understood the appeal of logic. Still, I couldn’t shake the sense that I wasn’t quite a person to her yet—just an input in an algorithm.
We ended the night with a brisk goodbye. And then went on to have five more dates.
In our emails and evenings, there was a matter-of-factness to K—a way she had of appearing only lightly tethered to this plane. As if she were simultaneously present in fifteen others, playing speed chess or coding a new world order. I found her idiosyncrasies both endearing and exhausting—often in the same breath.
Once, she told me she loved dance—as a spectator. I got us tickets to a Broadway-style history of dance at the Walnut Theater. She was spellbound, barely remembering to breathe. At intermission, I turned to ask how she was enjoying it, but she grabbed my hand and urgently gestured that we needed air.
We made our way outside, into the crowd of smokers. Then, suddenly, she began jumping up and down—repeatedly, for about a minute. When she stopped, she held my arms and said, matter-of-factly, that she sometimes had to do that when she got overstimulated.
Later, I would learn the term “flapping.” That night, I was just grateful no one seemed to notice.
Another time, she mentioned that her diet mostly came from vending machines. I thought it was a joke. But over the next two weeks, I learned she meant it: soda, candy bars, energy drinks.
I’ve always been drawn to quirky people—those wired a little differently. Maybe it’s because I’m wired a little differently myself. Looking back, many of her quirks suggest she may have been on the autism spectrum. I didn’t see it then, but it makes me feel a complicated tenderness now—for how much I didn’t understand.
At the end of one date—another long walk in the cold—she casually mentioned needing to get divorced. I stopped walking. Her profile had said she was single.
When I questioned her about it, she simply said she felt single.
She’d married someone while at Moscow State. He’d built a promising internet business that had threatened a mafia-run industry. They fled the country, going separate ways for safety. She hadn’t seen him since.
Then there was the night she was an hour late meeting me at the university bookstore. This was pre-smartphone ubiquity, so I just waited. When she arrived, arms full of books and papers, her first words were: “Robert, this is your fault.”
She explained she’d been in the psychology library—researching me. “I think your many homosexual friends stem from unresolved maternal conflict… I believe you are a latent homosexual.” She gestured to her stack of papers like a prosecuting attorney presenting evidence.
I asked, calmly, “What do you want me to say, K?”
A week earlier, she’d struggled to understand how I—a straight man—could have close gay friends. I’d explained my involvement in my company’s LGBTQ+ affinity group. But it hadn’t landed.
There was no dramatic goodbye—just a quiet understanding that it wasn’t going anywhere.
Still, I wasn’t ready to stop. Not because I thought she was “the one.” But because I needed to prove to myself that I could try. Even if it was awkward. Even if it was absurd. Trying meant I wasn’t stuck anymore.
They weren’t bad dates. They just weren’t a beginning.
But just when I thought things were coming to a natural close, she told me to take my birthday off. She had a surprise planned. A day of adventure in New York, she said.
What I got instead was a birthday I’ll never forget—and not for the reasons you’d hope.
But that’s tomorrow’s story.
Thanks, Mary.
Yes—there’s something timeless at the core of this one. The tools and social norms shift (matchmakers, lonely hearts ads, web dating, swipe culture…), but the awkwardness, hope, confusion, and—if we’re lucky—those flashes of pure connection remain, don’t they?
Just...wow. That's quite an adventure. 😳