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“Do You Think This Conversation Is Going Well?” and Other Pickup Lines

By

Dispatch

Guests at the Readme launch party. Photographs by Matt Weinberger.

Dreams can come true, and in dreams begin responsibilities. On a Thursday in September, I embarked on an evening of the sort of arduous New York City fun I used to fantasize about as a suburban seventeen-year-old in the year 2000; if I were so lucky as to one day make it here as opposed to anywhere, I’d be breaststroking in a riptide of scene and culture.

Chelsea was balmy and abustle with people in rumpled linen and statement eyeglasses entering and exiting openings. I did the same, then walked in too-tight loafers to the Lower East Side, where there was a hot party with a tight door. I had RSVP’d twice and requested a plus-one for good measure but was not on the list. Luckily, I was unfashionably early. “You’re fine,” said the lady with the iPad, and she waved me past the proverbial velvet rope. Funny Bar’s caliginous interior soon filled up with a young and attractive crowd gathering to toast the launch of Readme, a new dating app aimed at people who can, and maybe actually do, read books.

Mysteriously, the books that lined the bar’s shelves had their spines facing the wall. Ungenerously, I took this for booksmaxxing by the kind of insipid interior designer who hauls in yards of random used titles from the Strand to cast a learned-and-lettered penumbra while concealing their identities lest one or another ruin the mood. I dug around to discover copies of Trick Mirror by Jia Tolentino, White Noise by Don DeLillo, and Myra Breckinridge by Gore Vidal. I spied Amia Srinivasan’s The Right to Sex tucked into someone’s handbag—whether it had been purloined or brought along in case the party hit a lull, I’ll never know. People drank lemon drops, squished into a photo booth, danced in a DJ pit to sounds by Honey Bun, sampled the swag (pens, lighters, baseball caps asking “Is language your love language?”), and doodled ballpoint graffiti on paper-covered tabletops (“Cheers chairs stairs,” “blink blink blink,” “It’s all going tits up”).

Banu Guler and Emily Segal. Photograph by Michelle Paradis.

Readme is the brainchild of the brand strategist and creative director Emily Segal, in collab with Banu Guler, the founder and CEO of the astrology app Co–Star. They cohosted the party with the internet cynosure Caroline Calloway, the novelist Stephanie Wambugu, the poet Kyle Carrero Lopez, the writer and filmmaker Marlowe Granados, the fashion podcast Nymphet Alumni, and the vintage clothing store Women’s History Museum. In line for a drink, I chatted up a poet whose day job is working as a receptionist at a psychiatric facility in a neighboring state. We got to the heart of matters: she was out and about after a yearlong dating fast, a reset occasioned by a former boyfriend who’d threatened to kill himself if she left. She left anyway and her ex remained alive, unlike a patient on the ward the doctors had possibly released too soon, who promptly lit himself on fire in the parking lot. She liked tall men, and we surveyed heads poking helpfully out of the fray.

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When I video-chatted a few days later with Guler and Segal to discuss the inspiration for and the making of Readme, I asked if there was an in-app widget that users could toggle to integrate their star chart with their dating profile. “We’re pretty focused on literary taste right now, more than astrology,” Guler told me. “I love astrology but we could never quite figure out how to make it feel emotionally complex enough for something like a dating app. It’s just one piece of the entire thing.” She suggested matches compare their Co–Stars on the night of the date, “or the morning after.”      

Caroline Calloway. Photograph by Matt Weinberger.

The press materials position Readme as the digital version of a bookstore meet-cute. “It’s that feeling of falling in love over a book, over a poem,” Guler said. “And scouring each other’s bookshelves. It feels very different from how I use astrology with people whom I’m dating or talking to. Or, was talking to.” She held up a wedding-ringed finger.

“People have wanted Co–Star to build a dating app forever,” Segal said, but it was important to her and Guler that it happen “in a way that felt interesting and progressive.” Segal was formerly a member of the trend-forecasting collective K-HOLE, which, in addition to publishing bulletins such as “Fragmoretation: A Report on Visibility” and “Prolasticity: A Report on Patience,” coined the term normcore.

“Our own experiences of love,” she continued, are “the opposite of the flattened, performative, clichéd dating-app type of love. I think of the book that I gave my spouse the weekend we got together, The Little Virtues by Natalia Ginzburg, and the inscription I wrote in it, and how it became part of our lore. They say that they manifested our relationship, because before we got together, they dreamed of someone they could read with in bed every night before going to sleep.” Segal added that Guler had sent her partner a PDF after their first date. “What was the PDF?” I asked Guler. A long pause. No comment. Fair enough.

Readme’s design is a close cousin of Co–Star’s—the font, the muted color scheme, the koan-filled prose style. And the dating app has engineered what one might call an Enneagrammatical system of bookish star signs. When you onboard yourself, you are given a quiz you are instructed not to overthink that will enable Readme to “read you like a book.”

Our matching model is grounded in Lacanian psycholinguistics. It uses your language preferences to analyze how your desire is organized. For Lacan, the subject is constituted by language … we are all decomposed by language and imperfectly knotted together by the law of the signifier.

It goes on in this vein, describing three axes that chart a person’s relationship to language and by extension literature, and therefore somehow possibly also to love and romance. The axes are metaphor versus metonymy, spare language versus elaborate language, and then a z-axis encompassing “The Imaginary, the Symbolic, and the Real.” Of spare versus elaborate language, Readme says:

This axis measures how you express the impossibility of desire. It maps the subject’s relation to castration, i.e. to the bar on jouissance that constitutes it as an excessive, ungovernable vitality. The spare register accepts the limit, while fantasizing about a heroic overcoming of it—a hypothetical exception that only serves to prove the rule. The elaborate register neither accepts nor refuses the limit but gestures to something beyond it. This produces an overflow of meaning that results from a lack of limitation, an incomplete cut.

🤯🤔😵‍💫 Parsing this thicket of methodology, I confess to feeling a bit out of my depth or element, as when someone says they’re a Taurus with a Jupiter conjunct midheaven in Gemini, and/or/also like a man at the launch party wearing a T-shirt that read, “Sorry if I looked interested, I’m not.” The quiz itself is quite fun, though. You are presented with fifty unidentified passages of literature, two at a time. You swipe right on the one you like better, and the author of your preferred passage is revealed. That’s it! Why do I pick “Two interesting characteristics distinguished Leonard Blorenge, Chairman of French Literature and Language; he disliked Literature and he had no French” (from Pnin by Nabokov) over “The tears that had been absent at the funeral appeared, burning her eyes and stinging her throat. She tried to breathe, but it came in as a choking gasp. Margot pressed her sleeve across her face as she tried to stop the flow” (from Ray Bradbury’s short story “All Summer in a Day”)? I suppose because the first makes me laugh, whereas the second is about weeping.

Readme questionnaire.

My answers get fed into Readme’s proprietary psycholinguistic maw and I receive my archetype: the Resident Artist of the Undertow. “You think you want someone who will transform you into the kind of person capable of grand poetic gestures. Who will run into your arms on a stormy night as rain and tears and snot and saliva mix on your faces,” I learn. “But you’re not really ready to perform the melodramatic scenes you write in your mind. What actually ensues when you attempt them is a Beckett-like stalemate, frustrating and comedic, full of misfirings and false starts. ‘I can’t go on; I’ll go on.’ ” Readme then supplies a couple of icebreakers my type might want to ask on a first date:

What did you eat for breakfast?

Can you tell me a joke?

Would you enjoy a month of total solitude?

Do you think this conversation is going well?

They have a soupçon of the autist, but it is true that I could stand at times to be more plainspoken.

Guests at the Readme launch party. Photograph by Matt Weinberger.

There are eleven other archetypes in Readme’s arsenal, and they sound much less dreary than mine. The Biggest Fan of Reality is reassured that “freaks of all kinds” can be “self-possessed and attuned to the everyday: think of Samuel Delaney prose tripping out on a coffee cup,” while the Former Gifted Child is told, “Some people need the austerity of a vipassana retreat to get in touch with themselves. You need something else entirely: MDMA therapy, a forest rave.”

Whatever your archetype, the app’s reading recs are pretty fire. They include Love’s Work by Gillian Rose, Veronica by Mary Gaitskill, Malina by Ingeborg Bachmann, Asa, as I Knew Him by Susanna Kaysen, Selected Amazon Reviews by Kevin Killian, Hunger by Knut Hamsun, He Who Searches by Luisa Valenzuela, If You’re a Girl by Ann Rower, The Way of All Flesh by Samuel Butler, Fortress Besieged by Qian Zhongshu, A Voyage Around My Room by Xavier de Maistre, Sleepless Nights by Elizabeth Hardwick, The Pillow Book by Sei Shōnagon, Paradise by Abdulrazak Gurnah, The Moviegoer by Walker Percy, Enormous Changes at the Last Minute by Grace Paley, Love in the Time of Cholera by Gabriel García Márquez, Parable of the Sower by Octavia Butler, The Cattle Killing by John Edgar Wideman, Herzog by Saul Bellow, After Claude by Iris Owens, The Remains by Margo Glantz, and Bonjour Tristesse by Françoise Sagan.

At the party, the IRL merrymaking was such that a person could be forgiven for forgetting altogether that this was a bris for an app. I buttonholed everyone about the last book they had read start to finish. Among those cited: Rent Boy by Gary Indiana, Famesick by Lena Dunham, The Woman in White by Wilkie Collins, Heated Rivalry by Rachel Reid, Hotel du Lac by Anita Brookner, Fear and Loathing in Las Vegas by Hunter S. Thompson, Água Viva by Clarice Lispector, In a Lonely Place by Dorothy B. Hughes, My Body by Emily Ratajkowski, M Archive by Alexis Pauline Gumbs, The Second Coming of the KKK by Linda Gordon, The Last Temptation of Beck by Josephine Riesman, and the third movement of A Dance to the Music of Time by Anthony Powell. As the evening got more disheveled, I encountered other books as people pulled down copies of The Philosophy of Andy Warhol by Andy Warhol, Blockchain Chicken Farm by Xiaowei Wang, Blood and Guts in High School by Kathy Acker, The Wager: A Tale of Shipwreck, Mutiny and Murder by David Grann, Creation Lake by Rachel Kushner, Bastard Out of Carolina by Dorothy Allison, and Weegee’s People by Arthur “Weegee” Fellig.

Emily Segal and friend. Photograph by Matt Weinberger.

I downloaded Readme for science and didn’t actually join the beta to swipe around. But it seems promising, in a quality-over-quantity way. Segal told me that at the party, she and Guler “did see people downloading the app. We saw people matching on the app. We saw people meeting in real life and making out in real life.” I stood corrected for having judged the books on the wall by their unknown covers; Segal confirmed that the collection had been specially curated for the launch.

Meanwhile, Feeld is publishing its third issue of A Fucking Magazine. At long last, dating apps are capitalizing on what four-eyed monsters have known forever: reading books is cool and sexy. Like Joan Didion, the apps have made it an aesthetic. The Readme press kit’s party pictures had a throwback feel—United Colors of Benetton x the Cobrasnake. A frumpy publishing event it was not.

Did it leave me feeling commodified? Perish the thought—I felt desirable and vindicated. But my pinkie toes had blisters and my boyfriend had abandoned the line outside Funny Bar to stand in the line outside Katz’s Delicatessen, a more straightforward meat market. I shirked what remained of my reporting duties to join him right at the front. We split a pastrami sandwich.

 

Gemma Sieff has worked on the editorial staff of The New York Review of Books, Harper’s Magazine, and Town & Country. Her debut novel, Dear Charlie, will be published by Farrar, Straus and Giroux in spring 2027.