In Brushes with Greatness, Naomi Fry writes about relatively marginal encounters with celebrities.

Recently, an article I had read in an Israeli women’s magazine when I was maybe eleven popped into my mind. The piece was about fans: people who spent a lot of their time following their celebrity idols around, splitting the difference between adoration and what would now be probably called stalking. I recalled a detail about two sisters who were obsessed with, if memory serves, Kris Kristofferson. Somehow, they had ended up at one of his houses, where a housekeeper let them in and was kind—or unprofessional—enough to give them some mementos of their idol’s: a pair of old cutoff shorts he wore out of the shower and some cigarette butts that he’d smoked. Cigarette butts that he’d smoked! This struck me both then and now as kind of extreme. Imagine being so earnestly fixated on a stranger that touching something that carried only the faintest imprint of his or her body—even something fairly gross like an old cigarette—would be a thing you’d seek out!

Decades have passed, and today very few celebrities still inspire that kind of all-out adulation, engendered by real distance between the famous and nonfamous. The kind of stars I’m thinking about—Beyoncé, maybe Rihanna—have a spectacular untouchability that gives rise to the traditional model of fandom: the type that wants to touch, that desires the laying on of the hands, or at the very least a whiff of the raiment. (Think, for instance, of Drake—a big star in his own right but also, too, a known superfan of Rihanna’s—who, in a song originally meant for her to sing, wrote the lines, “Let my perfume soak into your sweater.”) 

For the most part, though, our interactions with celebrities have become a lesser, much more offhand, business. This might have partly to do with the replacement of the tactile with the virtual. The wished-for end result of most encounters with a celebrity nowadays is a shared selfie (instead of, say, the more tangible souvenir of an autograph), quickly taken and disseminated rather than retained. And a dalliance between a famous person and a fan can easily take the form of sexts rather than real-life sex: the proof positive is no longer something like semen on a dress that is then tucked away for safekeeping in a closet, but swiftly shared screenshots or dick pics.

These more casual engagements are not only more common, but also more malleable and ambivalent. Easier to come by and more unceremoniously pursued, they can be enacted in a manner that’s simultaneously detached and earnest. I’m thinking now, for instance, of a recent Instagram picture of a friend in which he posed for a selfie at Nobu with Kylie Jenner, the youngest member of the Kardashian clan. While I doubt the friend would call himself a fan of Jenner, exactly, there he was, looking very pleased with the encounter he was sharing. And why wouldn’t he be? In his place, I would have asked for a selfie, too, and shared it widely besides.

It was a funny moment, of course: the humor predicated on the camp value of a grown man of generally high-brow-ish tastes getting his picture taken with an eighteen-year-old reality superstar–cum–tabloid princess. But there was also a hint of the old dynamics of an encounter with fame; the moment of celebrity/civilian acknowledgment—no matter how brief or seemingly meaningless—still carried an enticing weight and texture. And if you’ve been lucky enough to have your head nuzzle side-by-side, if only fleetingly, with that of a person more famous than yourself, your eyes turned as one toward a camera phone’s lens, you know this to be true.

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Not long ago, I had my own virtually mediated encounter with a star, though star might be slightly stretching it: the man in question was Justin Brescia, formerly of MTV’s The Hills, where he was known, somewhat smirkingly, as “Justin Bobby.” A spin-off of the rich-teens-in-the-OC reality series Laguna Beach, The Hills focused on that earlier show’s protagonist, Lauren Conrad, as she moved at eighteen from her wealthy beach community to LA, where she interned and partied in various West Hollywood lounges with her good-looking peers in the fiddle-as-Rome-burns, pre-market-crash days of the mid-2000s. Justin Bobby joined the cast in The Hills’s third season in the minor role of a sexy bad boy about town, the slippery love interest of Conrad’s hot but dead-eyed friend, Audrina Patridge.

The older you get, the more idiotic the accouterments of the rebel’s costume begin to seem—the motorcycle, the leather jacket, the scruffy hair, the tattoos, the cryptic, noncommittal faux insights. Justin Bobby checked all these boxes and more. (When asked by Patridge where their relationship was headed, he raked his longish curls back from his handsome, stubbly face and intoned, “Truth and time tell all.”) Then again, idiotic doesn’t necessarily mean ineffective, and the thing about the figure of the bad boy is that it’s usually as attractive as it is embarrassing. You (me), the married, bespectacled Jewess writer in her late thirties, are simultaneously too good for someone like Justin Bobby and yet not quite good enough. It would be mortifying to consort with his type, but, hypothetically speaking, would you (me) ever get to have that chance in the first place?

This is how it all went down: A couple years ago, with Justin Bobby largely removed from the public eye, I was joking around on Twitter with a friend, wondering whatever happened to him. Where have you gone, Justin Bobby? I tweeted. Not two minutes went by and Justin Bobby was sliding into my DMs, ready to engage—he must have been searching for his name on the site. Amused but also excited by this turn of events, I expressed my admiration. “I love you Justin Bobby!” I believe I messaged, to which he replied, “Ah, bless ya.” My only goal at the moment was to continue the conversation, no matter how insipid—I was collecting my own kind of cigarette butts.

Then Justin Bobby asked me my age. I guessed he was attempting to see whether I was legal, a funny thought since I was, at the time, thirty-eight. (Though it’s true you can never be too careful!) Still, what if he was trying to check not whether I was too young but whether I was too old to be viable? “Too old for you, Justin Bobby,” I messaged vaguely. “I’m an old man, I’m thirty-two,” Justin Bobby wrote back. And then: “Do you Skype?”

I had been with my partner for more than a decade by that point, but even I had heard enough about interaction between men and women on the web to guess that the Skype thing meant, likely, that Justin Bobby wanted to show me his penis. This in itself did not sound like an attractive proposition to me. The conversation-piece value of such a prospective encounter, however, was worth its weight in gold, and the longer I could keep Justin Bobby engaged, I knew, the better story it made for. But also, I felt weirdly, earnestly flattered, in a way I was mortified about but couldn’t totally help. I was nearing forty; how much longer, I wondered, would marginal but raffishly handsome reality show actors appear in my DMs, obliquely clamoring to share their privates with me?

In the face of my silence, Justin Bobby persisted: “How old are you, hon?” Since this conversation was happening on Twitter, I took to Facebook, away from Justin Bobby’s potential oversight, to share the news and get some advice. But while I was basking in my Hills-watching friends’ mostly unhelpful glee (“KEEP IT GOING. YOU HAVE TO DO WHATEVER IT TAKES TO KEEP IT GOING,” one commented), I was still unsure how to play the sudden hand I was dealt. After some deliberation, I decided to speak my truth: “I’m thirty-eight, Justin Bobby,” I finally DM’d. No response! And then, a day or so later, an unfollow.

I was a little offended, of course, but mostly relieved. Already, I was spinning the whole thing into something I could tell and retell. It had enough texture to make it memorable, some shameful and earnest yearnings, some comic relief: to me, it seemed a near-perfect celebrity encounter. And the lack of a money shot, the absence of climax—of this I was sure—would be what made the story even better.

Naomi Fry is a writer and the copy chief at T: The New York Times Style Magazine.