Observational Proficiency
Why would a former supermodel be interested in a guy like me?
[A note for the reader: I performed this monologue as part of an occasional series called Library Girl at the Ruskin Theatre in Santa Monica, California on February 8, 2026. The theme of the evening was “You Walked In And My Life Began Again.”]
My first notable accomplishment came on May 14th, 1973. I was nine.
A large crowd has gathered outside Fernbank Science Center in Atlanta, Georgia. Upturned faces scan the night sky. Yet it was little I who, on that historic evening, spotted Skylab, not long after launch from Kennedy Space Center, arcing across the heavens. And for this I received a certificate which I still have. It says “In Recognition of Observational Proficiency.”
Did I peak at that moment? One would assume so. But then years later I ended up writing for a bunch of TV shows you’ve probably heard of. And then that was upstaged by a stunning third-act turn:
I am the boyfriend… now fiancé… of a former supermodel… I met on a dating app.
Why would such a woman be interested in me, you and everyone in the universe and social media may repeatedly ask repeatedly?
There are two answers to that question — one superficial, the other less so.
Superficially, it’s because I picked a good song to go with my profile pictures.
I hesitate to share this, ’cause it’s a ringing validation of the Nick Hornby/John Cusack/High Fidelity worldview that if you could just assemble the platonic ideal of a mixtape, you could make anyone fall in love with you. That the perfect song can somehow ensnare the perfect woman.
Yet in my case it happened.
On the app we were on, here’s what a profile consisted of: Eight to ten photos, soundtracked with a song of your choice. A brief self-description. And a link to your Instagram.
My profile pictures were a disaster — I learned this much later, unfortunately. Might’ve been smart to ask one of my excellent collection of excellent female friends to vet my selections, yet I was too shy to do that. So I chose some truly tragic photos:
- Jeff with the rimless glasses he thought made him look like Steve Jobs, but which he later learned cast him as a dentist in a David Cronenberg film.
- Jeff holding a vintage Polaroid camera — yeah, that doesn’t scream “creepazoid” much.
- Jeff with his ’66 Volvo — women love seeing your car. Only thing better is you holding a fish.
And then there was my description of myself — also catastrophic, as it turned out:
- Six foot seven. True, but I’ve since learned it’s a freakish and off-putting number. Most guys round up. “Six seven,” however, says you’re eight feet tall, rounding down so you don’t terrify people.
- Ambidextrous. Why was I telling women I don’t know which hand to use?
- Southern, but you can’t tell till you know me. Why was I telling women I could be a closet racist?
- And finally — Greatest accomplishment: convincingly mimicking the traits of an extrovert. Why was I telling women I believe lying is what I’m best at?
As for my Instagram, at the time it was a meager showcase for my hobby of analog photography. Hence my eight followers were occasionally treated to grainy black-and-white photos of plants and buildings. It was the Instagram of a serial killer.
Bottom line, what I was offering was disaster, catastrophe, Buffalo Bill from Silence of the Lambs. Where was the vaunted observational proficiency? It’s amazing any woman liked me at all.
Yet one did. As I said, it was only the musical taste that saved me. And now I see all you John Cusacks leaning forward, breathlessly awaiting what that One True Song was which turned the tide. You are never going to believe it. Here it comes:
The song was “Modern World” by Jonathan Richman and The Modern Lovers. Maybe you’ve never heard of Jonathan Richman. Maybe you only know him as the adenoidal troubadour from There’s Something About Mary. But the music nerds among you, the ones who do know him, I’m sure are astounded.
Turns out I’d inadvertently struck a pleasure center. My gal loves Jonathan Richman. Her oldest son’s named after him. An ex-Modern-Lover was in her late husband’s band. So “Modern World” was the ideal song, despite my boldly promoted shortcomings, to pique her interest.
Her song, by the way, was “The Galaxy Song” from Monty Python’s Meaning of Life. Now there’s a strong choice — funny song about astronomy! Count me in!
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So we connect, begin texting. And then, apropos of astronomy, I told her when I was a kid I wanted to be an astronaut, but soon grew too big for the space capsule. “When you were a kid,” I asked, “what did you think you wanted to be?”
Now, my fiancée has been interviewed a lot over the years. She’s been on a lot of first dates. Yet she later told me no one had ever thought to ask her that question.
Her answer? “A cleaning lady or a postal worker.” How great is that?
We text some more, really enjoying each other. And then, since I was stuck in L.A. on a TV job, I asked if she might like to brew up some tea and talk on FaceTime.
At this point I feel obliged to note what should be blindingly obvious: My expectations were rock-bottom. Nothing’s gonna happen here. She’s fabulous, I’m not. She’s East Coast, I’m West. At best I’m going to add one more to that excellent collection of excellent female friends. But why not?
So we get on FaceTime, sip our tea, and we talk. She’s incredibly funny. Dazzling intellect. Best-read person I’ve ever met. And over the next few weeks we progress from tea to white wine to tequila and the conversations get longer and longer. The last went six hours. And I wanna stress, nothing sexy’s happening on the FaceTime. We’re just talking, laughing, and getting to know each other.
Meanwhile, what I fail to realize is, on her end she’s confused. Why isn’t this guy advancing an agenda? Why isn’t he asking me out? She’s accustomed to being pursued — avidly! Yet this guy wants to talk? It was, I guess, intriguing!
Of course you know why I’m acting this way. Because I am a worm, and no woman would ever want to be with me, particularly a fabulous one. So in this case, and only this case, low self-esteem did me a favor!
This chatting goes on for a month. And then one day she sends a fateful text: “I love talking to you. We have a surprising amount in common. And that makes one feel… kinship? Recognition? Definitely interest. So when are you coming to New York?”
Uh, how’s this weekend??
And then it was on, and it’s still on. But I gotta rewind for a moment. There was something in our first conversation which turned out to be — Wait, gotta rewind some more.
The year before the events I’ve described was a very rough year. It started okay — signed up for the dating app, got a new job. But then on the first day of work I was awakened by a terrible phone call: My sister’s boyfriend, her law partner, her partner in every part of her life, had died suddenly.
Everything stopped — the job, dating. I set everything aside and for the rest of the year just helped my sister. Calls every night at bedtime, trips to Atlanta to help piece her life back together… Nothing else mattered but being of service to a loved one in pain.
Now, return to that first FaceTime call with the gal in New York. Kind of our first date.
“So,” she asked, “you were married?”
“Yeah,” I said, “for twenty-five years.”
“What went wrong?”
I don’t know why I responded this way, but here’s what I said:
“Well, if you were to ask my ex, she’d say she married a raging narcissist who sucked up all available light, so she was perpetually in shadow and could never blossom into the person she was supposed to be.”
“And is that true?” she asked.
“It’s a little bit true.”
Why. In the world. Would you say that? Open with the most unflattering self-portrait imaginable? That’s beyond a rookie mistake. That’s Bill Buckner World Series, Scott Norwood Wide Right — a fiasco.
But now I gotta swing around to the gal on the other end of the call.
She later told me this was one of her stock first-date questions. If you’re on the dating market in your fifties, clearly you’re some kind of broken toy. So she’d ask the guy what went wrong in his last relationship. Invariably he would say, “Oh, it’s so sad, but she had borderline personality disorder.”
You think I’m kidding. She swore they said this eighty percent of the time.
So when the man she’d just met not only didn’t say that, but — before even sharing his own version — told the story from his ex’s point of view. And copped to the fact it was valid. That was… unusual, to say the least.
Also dumb. You’d never do that, right? Admit to a narcissistic streak? Say you might’ve wrecked the relationship? Why’d I do that?
Maybe because of those months of service. Of setting aside my own needs, being just a little more selfless. And perhaps in doing so realizing how much the rampaging ego had been running the show up to that point.
So the other answer to the question, why would a former supermodel be interested in me? Besides my love of Jonathan Richman? Apparently it was that unexpected display of observational proficiency. Something I hadn’t shown that much since I was nine.
