Lonely Bois: On Dan Humphrey's 'New Yorker' Story in Gossip Girl
Also discussed: the literary works of Caroline Calloway, romantic misadventures in Aix-en-Provence, novelists on Twitter, the male gaze, Netflix's 'You'
With everything going on right now, it would be wrong *not* to talk about Dan Humphrey’s story being selected for The New Yorker’s 20 under 20 summer fiction issue in season one of Gossip Girl…
Sam: …which of course I've been revisiting ever since it was put out on HBO Max, because I have no life and now it feels "prestige."
Joe: It’s HBO-lite. Which is to say: It’s HBO Max.
Sam: My rewatching dislodged this one detail that got stuck in my brain sometime during the spring of 2013, while drinking 2 euro cooking wine on the unwashed futon of a humid one-bedroom apartment in Aix-en-Provence where we were spending our semester abroad (and where, evidently, we also had no life). In the episode, Vanessa (Jessica Szhor) informs her friend, Dan Humphrey (aka, Lonely Boy, aka Penn Badgely), that she’d secretly submitted his story to The New Yorker—and that it’s being published in their 20 under 20 summer fiction issue.
Joe: Remember the bodega by you upped the price of that 2 euro wine one day because we’d bought so much? It was like economics class in action.
Sam: Our “brand loyalty” to Pichet Club was...dark.
Joe: But go back to Dan.
Sam: Here’s what we know about his short story:
1) The title is "10-08-05.”
2) It’s so-named for the date he first laid eyes on Serena van der Woodsen (Blake Lively), the queen of the Upper East Side and his then-girlfriend, who, if I recall, was stumbling drunk and helpless into the middle of the street after partying at, I don’t know, 1 Oak or something.
3) He wrote it longhand and probably compared his pining for Serena to “an insatiable hunger” a lot?
Joe: (Remember when authors used to describe penises as “pricks”? Don’t see that too much, anymore…)
Sam: There are several reasons I love this whole bit. Namely, it’s a prime example of the kind of half-truth—there IS a summer fiction issue of TNY; there IS NOT a “20 under 20”—that Gossip Girl was so adept at. Myriad other examples of the show’s ability to cheekily blend fact and fiction abound, although my all-time favorite (after TNY) is Jay McInerney’s cameo as a novelist Dan interns for, because novelists used to have interns?
Joe: Bright lights, big...unpaid internship?
Sam: But what the “20 under 20” thing really offers is such a specific kind of wish-fulfillment. At that age—really, at this age—what could be more appealing than having your first story, written about your first love, published in The New Yorker? And, on top of that, losing your virginity at a Brooklyn-based art gallery to the girl you wrote the story about? Who looks like Blake Lively?
Joe: Yeah. Though by the time we watched this any chance of that happening to us had passed us by.
Sam: (Contrary to what we may have led some readers to believe, Joe did not write any short stories about his high school girlfriend. He was, however, Seasons Soloist #2 in the HPHS production of Rent in which she starred.)
Joe: What I’m trying to say is, whose fantasies are really being projected here? Ours? Or co-creator Josh Schwartz’s? After all, this isn't the first time we've seen a teen drama where the main character is/wants to be a fiction writer (see: Schwartz’s Looking for Alaska, and even The O.C.). It's almost like that old (and old-fashioned) trope where every NBA star wants to be a rapper and every rapper wants to be an NBA star. Except it's like every Jewish teen soap showrunner wants to be a novelist and every novelist wants—if not to be on a teen soap—then at the very least to think themselves as important or romantic or dramatic or wealthy enough to be a character on a teen soap.
Sam: Or successful enough to write an HBO show.
Joe: Maybe it just boils down to the simple fact that people romanticize writing and reading way more than they actually want to write or read, because those things are hard.
Sam: Despite how easy we make it look on this Substack…
Joe: This episode typifies that romance of writing>than writing itself equation—
Sam: Math?!?!?
Joe: —where Dan’s writing (his, like, first story ever) is really only in service of his love story with Serena. It’s a “gift” not in the intangible literary sense, but in the literal, object sense: It’s what Vanessa gives to Dan, and then, later, in that gallery space, what Dan gives to Serena, surrounded by screens projecting animated snow.
Which is ironic: the entire point of the episode is that Dan/Serena want to give each other “authentic” (i.e. thoughtful, not expensive) Christmas gifts; but those very “gifts” are really just about converting Dan’s art into socio-cultural currency. Being in The New Yorker buys him entrée into Serena’s strata—and her pants. Thereby revealing the other great truth of writing, which is that writers write to get laid.
Sam: That penultimate scene also dramatizes the act of writing as of form of romantic wish-fulfillment: He goes from watching her (i.e., writing fiction) to being inside of her (i.e., participating in the reality his fiction reifies).
In general, it’s interesting to note how the conception of this Lonely Boy literary type has evolved, even just in the past decade. Badgely’s latest TV performance, in You (see above), is a pretty overt take on Dan Humphrey, updated for the #MeToo generation. The same well-intentioned "good guy" protectiveness—or "watchfulness"—that was framed as innocent and romantic in GG is presented, in You, as toxic, dangerous, deadly. He’s not the novelist qua TV showrunner, but the wannabe novelist qua serial killer—a lit-bro incel.
Joe: It’s like the show is apologizing for its predecessor, for not realizing that Dan in all his male artistic excess and manipulativeness was dangerous. It’s less sanguine about the power of social media that GG foreshadowed, too. It’s a portrait of the artist as a young surveillance state, not as the innocent voyeur.
Sam: Maybe what we’re really dancing around is the (destructive) male gaze. You exemplifies the insane response some “lonely boys” experience as a result of the loss of real or perceived “ownership” over a woman: her image, her likeness, her story. And this is playing out today as (predominantly female) influencers and models become creators and entrepreneurs, the managers of their own modes of production.
Joe: Shout out to Em Rata’s essay in The Cut, which articulates this better than we could. Also shout out to this being the second post in a row where we’ve mentioned Em Rata.
Sam: The idea of the male (and straight and white and Western) gaze is obviously one of the most pressing issues in contemporary fiction, too. Who gets to tell what stories? In Gossip Girl, Serena is tickled by Dan’s story about her; in You, the narratives Joe constructs about his crushes become oppressive, violent, consumptive.
Joe: It’s still all about control, though, isn’t it? Because writing fiction is perhaps the ultimate exercise in control. I actually think, to tie it together, it’s precisely this notion that makes fiction writers, barring a few exceptions (e.g., Brandon Taylor), so meh at or uninterested in social media.
Sam: Yes, yes, speak on that, get yourself ripped to shreds by literary Twitter…
Joe: Well I feel like there’s got to be this (subconscious or not) drive to protect their public image, so as not to influence the read on the thousands of words they’ve toiled over and perfected in private. Performing on social media competes with (and potentially colors, for better or worse) their fictional performance—thus ceding some control of that fictional performance. Problem is, in order to sell books, especially these days, writers tend to have to sell themselves, too.
This tension has always existed, but social media intensifies it. Unlike novels, which are predicated on a lack of a unifying “truth,” Twitter and Instagram still largely insist on demonstrating the existence of an objectively real or true person somewhere behind the scenes: the one without makeup, or crying, or being courageous by telling followers, “This is not the real me.” This has its corollary in autofiction, which often reveals the “writer” behind the “fiction” (albeit still in an ostensibly fictional light).
The critic Christian Lorentzen makes a really compelling argument that in the age of autofiction, novelists have become less probing voyeur and more self-conscious product—more Jay McInerny on TV than Jay McInerny. As he puts it:
“Writers become the opposite of the spy: They must always be just what they appear to be, because their job has ceased to be distinguished from self-promotion.”
I should add that I’m not making a value judgement on any of this.
Sam: I would also add that the heightened sensitivity around who’s writing what has, despite any other downsides, facilitated a push for greater diversity in publishing.
Joe: And in general, if it helps get you published and/or sell your books, do what you gotta do. Why I else would I start a Substack?
Sam: I imagine if Lorentzen read this, he would loathe what I’m about to say next, but doesn’t his notion—of the writer becoming the opposite of a spy—sort of describe the arc of Dan in Gossip Girl? It brings to mind a side plot in the second season, when Dan pens a short story about his frenemy Chuck Bass (Ed Westwick) for “Noah Shapiro of The Paris Review”—naming his protagonist Charlie Trout (lol). Rather than publish the piece, Shapiro persuades Dan to use his relationship with Chuck to write an exposé on his hotelier father for his friend at New York Magazine (double-lol)—at which point, Dan must decide whether to remain a “spy” or make himself, the writer, part of the product.
Joe: Frenemies…writer-as-product…New York Magazine. All of this gets me thinking about the person who’s probably the closest to a real-life version of Dan Humphrey: Caroline Calloway.
Sam: A lovestruck Lonely Girl in Cambridge, mining similar insider/outsider dynamics…
Joe: …while also trying to bridge the gap between literary writing and social media.
Sam: In that respect, at least, she was destined to fail. The maintenance of a kind of "fiction" on Instagram is simply untenable, because unlike a book, Instagram never ends. Without enough life to sustain the story, Calloway's content, however entertaining, was always fated to collapse on itself, recapping and retreading ad infinitum the same tired dialectic: “This is the real me!”; “No! This is the real me!”
Joe: A lot of her persona at some point seemed to become this shtick: I will take anything bad someone says about me (scammer, elitist, etc.) and apply it to my own sense of self (thereby defanging it). And I don’t blame her. What else is someone constantly trolled online supposed to do?
Sam: Yeah. We’ve talked about Ziwe’s interview with her and why it was so cringe-y—and not only in the ways Ziwe intends those interviews to be cringe-y. It was as if Calloway was managing the response people would have to what she was saying in real time, attempting to convey she was in on the joke of quote-unquote “Caroline Calloway” while simultaneously being Caroline Calloway. You watch something like that and have to wonder: Is it possible to be so self-aware that you’re actually…un-self-aware? (Yes.) To me, Calloway is the ne plus ultra of internet personalities, in that her internet personality seems to have become increasingly premised on what people say about her on the internet.
Joe: But the writing takes a hit, doesn’t it? Having to constantly manage and manicure your image is fundamentally at odds with the (actually brilliant?) autofiction—yes, I’m calling it that—for which Calloway became Insta-famous in the first place.
Sam: Totally. Full disclosure, Joe and I separately purchased Caroline Calloway’s (three?)-part response to Natalie’s essay on The Cut, and I’m willing to go on the record as calling it “literature.”
Joe: Is Natalie the Vanessa to Calloway’s Serena? (How did I get here?) But, again, to quote Lorentzen, on Knausgaard this time, “The process of putting the life into writing in the end outweighed the life itself.”
Sam: Which on a meta level is more or less what happens to every TV show after six seasons. As a surfeit of story presses up against the bounds of believability, they have no choice but to become about themselves—over time, Gossip Girl becomes less about the lives of Upper East Siders, and more about characters in a show called Gossip Girl. The ultimate example of this is in Dawson’s Creek, where, after however many seasons, Dawson ends up directing a series that is for all intents and purposes Dawson’s Creek.
Joe: Though can you really blame Calloway or the creators/participants of Gossip Girl (or any show really) for wanting to keep it going? What do you really get for "finishing" a book these days? No one reads it and you get no money. Maybe, like Dan, you get published in The New Yorker and get to have sex with someone way out of your league.
Sam: It makes me wonder whether the Lonely Boy character in the forthcoming Gossip Girl reboot will be an aspiring fiction writer at all.
Joe: He’ll probably want to do TV. All the cool novelists are doing it.
Sam: It feels only fitting that I end this conversation by retelling a story I've told you several times before, set in Aix-en-Provence during our semester abroad, where, as I mentioned up top, we first started watching Gossip Girl (and first saw this episode).
It was junior year of college. I had just purchased a black leather jacket, which was promptly ruined in Marseilles during a rainstorm. The appeal of “taking walks” was quickly revealing itself to me. I suppose I was becoming serious about writing—or at least serious about wanting to become a writer. In between nights out, make outs, cheap wine, and Marby reds, I recall meandering through the maze-like streets, where I thought deep thoughts about trite things, like love, and sex, and do we become different people when we travel somewhere new?
One afternoon, I was writing on my laptop in an English bookstore—some fragmented essay-ish thing about the French girls I passed on the street who wore all-black, plus death—when out of the corner of my eye I spotted a blonde girl about my age, dressed in a nondescript evergreen top and acid-washed blue jeans, as if she'd sprung from our 12th-grade French textbook. I noticed she was very pretty, although I thought all French girls were very pretty. But there was something else about her, a certain je ne sais quoi, if you will, that I couldn't quite place—a tingly familiarity that clung to my gut, akin to the feeling you get when you see someone who broke your heart from across a crowded room. Then it hit me: She looked exactly like Blake Lively.
In my head, I ran through ways to approach her. I could no longer concentrate on what I was writing; I simply stared at the cursor, watching it blink. At some point I saw her get up to leave. But to my surprise, she headed towards me. I tried to keep my head down, to look focused. When she finally reached my chair, she said hello (in English, thankfully) and I said hello back. Then she asked me whether I was American; I said I was. Then she pulled out a slip of notebook paper and asked me whether I would read over a cover letter she was submitting, in English, to some university program in Ireland. I blushed. Of course I would. I read over it, glancing up at her between paragraphs. I made very few corrections; her English was, in fact, quite good. But as I read, I kept thinking about how I would get from this interaction to a date, a drink, a kiss, a story. When I was done, I handed her the paper back. She smiled shyly and said thank you. Did I sense, in her response, a certain nervousness? Before I could say more, she asked if we could exchange numbers. We could hang out sometime. We could? I couldn't believe it—couldn’t really fathom that that was even an option. Soon after she left I packed up my stuff to head home and tell my friends (aka, you and my roommate) what had transpired.
Well...you know what happened next. After an intermittent text exchange, we finally met up for a drink at a café in the square near our apartment. I remember it was rather chilly, around sundown. I smoked a cigarette to calm my nerves on the walk over, even though I never smoked cigarettes sober. The bistro where my roommate and I had shared a 24 euro steak tartare on our first night in town bustled with apero-related activity. And I arrived to find French Blake Lively...with a girl friend. Her girlfriend. They were waiting for me, laughing, conspiring, rolling cigarettes. We chatted for awhile, exchanging polite details about our lives. But my hopes had died as soon as I’d sat down and remained buried for the rest of the conversation. We were not to be. This Blake Lively was, I’m fairly certain, not even into guys.
More lesbian girl who looks like Blake Lively stuff.