Executive Overview
On a crisp, cloudless late-summer evening on August 26, New York City’s historic Seaport neighborhood served as the backdrop for an event that blurred the boundaries between high literature, urban folklore, and unadulterated romantic comedy. Docked on a massive, centuries-old tall ship—the oldest of its kind afloat in the city—literary curator Dream Baby Press hosted a one-night-only extravaganza aptly titled “I Love New York.”
Curated by Dream Baby Press co-founder Matt Starr in partnership with the South Street Seaport Museum, the event brought together an eclectic, star-studded lineup of cultural icons, politicians, actors, and writers to deliver never-before-told personal essays and slam poetry. For an audience of over 400 enraptured New Yorkers, the evening functioned as an unfiltered love letter to the Big Apple.
Yet, this was far from your standard, high-society poetry reading. Eschewing the quiet, sterile ambiance of traditional book-launch venues, the night leaned heavily into the chaotic, beautiful unpredictability that defines life in New York City. The anecdotes shared under a brilliant full moon ranged from the deeply absurd—including a post-surgical penile mishap at the Carlyle Hotel, a $40,000 diamond onyx cuff, and a grocery list of prosthetic penises procured for a James Franco film set—to life-altering strokes of financial serendipity.
As the cultural landscape of New York faces perpetual shifts driven by gentrification, corporate homogenization, and economic pressures, events like "I Love New York" serve as a vital reminder of why millions remain tethered to the metropolis. This feature explores the chronology of an unforgettable evening, the broader cultural ethos of Dream Baby Press, and what these urban chronicles reveal about the enduring romance of America’s most relentless city.
Detailed Chronology: A Night on the Seaport Deck
Setting the Scene: Twilight and Famous Sightings
As the sun dipped below the Manhattan skyline, casting a warm golden hue over the historic tall ship, attendees boarded the vessel to find an atmosphere already thrumming with anticipation. The weather had held—a rare, mercifully clear evening that spared organizers the logistical nightmare of rain contingencies.
Almost immediately, the evening established its uncanny knack for serendipitous encounters. Early arrivals spotted internet personality and writer Caroline Calloway navigating the deck, followed shortly by New York City Council Member Chi Ossé, who famously made history at age 23 as the youngest person ever elected to the municipal body.
These sightings served as a thematic premonition for the night ahead: in New York City, the ordinary boundaries of daily life dissolve, and you never truly know who—or what—is lurking around the corner.
Jemima Kirke and the Carlyle Hotel Anecdote
The literary readings kicked off with actress, artist, and Girls star Jemima Kirke taking the stage. Kirke delivered an exquisitely detailed, highly idiosyncratic account of an anniversary celebration gone sideways at the legendary Carlyle Hotel.
"My boyfriend and I were there for a night celebrating our one-year anniversary," Kirke recalled to the rapt crowd. "He had just had minor surgery the day before on his penis—he was in pain, and sex was out of the question. But like my acting teacher always says, ‘When you’re in the creative state, there is no such thing as distraction, only potential for inspiration.’"
What followed was a winding, hilarious narrative involving an unexpected run-in with Tessa Dahl—daughter of famed children’s author Roald Dahl—a broken anatomical feature, a $40,000 diamond onyx cuff, and the peculiar, old-world glamour of the Upper East Side institution. Kirke’s story set a high bar for the evening, proving that New York romance is rarely about candlelit perfection; rather, it is forged in the fires of shared absurdity.
From Bussy Boy Soap to Proctological Prop Departments
Following Kirke, the microphone was passed to playwright Max Friedlich, the creative force behind the critically acclaimed theatrical hit Job. Friedlich reached back into his college archives to perform a slam poem recounting a chaotic chapter of his early career. A simple text message from an old teacher had unexpectedly landed him a gig assisting James Franco on a movie set in Brooklyn. His primary duty? Sourcing an array of prosthetic penises for a climactic scene.
Council Member Chi Ossé took the deck next, recounting a quintessential Chinatown encounter with eccentric pop star Azealia Banks. According to Ossé, Banks handed him a bar of "Bussy Boy" soap—her male hygiene startup at the time—during a chance meeting. Years later, as he mounted a historic political campaign that successfully banned exploitative broker fees across New York City, Ossé joked to the audience: "I did that with the strength and power of Bussy Boy in my pocket."
Ossé also regaled the audience with an encounter involving Interview magazine editor Mel Ottenberg. While waiting for a drink, Ossé watched Ottenberg stroll past his group of friends, prompting one companion to utter a line that brought the house down: "I thought Mel Ottenberg was Black?"
The deck erupted into laughter. "New York City, baby!" Ossé grinned, capturing the exact brand of unfiltered cultural cross-pollination that makes the city tick.
The $100,000 Billionaire Gamble
Not all of the night’s storytellers were born-and-raised locals. Los Angeles-born actress and filmmaker Alexi Wasser took the stage to recount the universal immigrant and transplant experience: the moment one falls hopelessly, irrationally in love with New York from afar.
"I remember seeing model Jaime King, 15 years old, heroin chic, lounging backstage at a fashion show, smoking a cigarette on the cover of New York Times Magazine and thinking, ‘Oh, holy fucking shit, I have to move to New York!’" Wasser shared.
It took decades for Wasser to finally plant roots in the city, arriving around age 40. But New York rewarded her perseverance in cinematic fashion. She recounted a period spent working as a personal assistant to an anonymous billionaire. In a stroke of pure, unadulterated urban mythology, the billionaire wired her $100,000 to finance her first feature film—and then never spoke to her again. That miraculous, abrupt windfall ultimately funded her 20th-century-rom-com-esque 2024 comedy, Messy. Wasser’s tale resonated deeply with the crowd, offering a comforting reminder that in New York, a life-altering breakthrough can happen at any age.
Supporting Context & Metrics: Escaping the Algorithm with Dream Baby Press
To understand the cultural significance of the "I Love New York" event, one must examine the disruptive ethos of its creator, Matt Starr. Having lived in New York City for two decades, Starr has made a career out of subverting traditional art spaces.
Since its founding in 2022 alongside Zach Roif, Dream Baby Press has intentionally rejected the traditional white-cube gallery or the quiet academic lecture hall in favor of guerrilla literary pop-ups. Previous readings have been staged in some of the city’s most aggressively unromantic or hyper-mundane locations:
- A Sbarro franchise in Penn Station.
- An East Village adult video/porn shop.
- A neon-lit branch of Burger King.
- A gritty boxing gym in the Financial District.
"I wanted to do something that was my love letter to New York City, and figure out, ‘What would a real-life rom-com look like?’" Starr explained.
The Metrics of Urban Loneliness and Connection
Starr’s instinct taps into a profound psychological need among modern urbanites. In an era dominated by hyper-gentrification, soaring housing costs, and the isolating influence of dating apps and algorithmic matchmaking, physical, shared cultural experiences have become sacred.
According to recent data from the U.S. Census Bureau and local housing authorities, over 50% of New York City households are occupied by single individuals—one of the highest rates of single-person households in the Western world. Concurrently, average rent burdens in Manhattan and Brooklyn routinely consume upwards of 50% to 65% of median tenant incomes. Living in New York is, objectively, an exercise in financial and emotional endurance.
Yet, as the night on the tall ship demonstrated, the city’s residents actively seek out spaces to collectively laugh at their shared suffering. Complete with printed "flirtation cards" scattered across the vessel and string lights flickering under a full moon, the event intentionally mirrored the aesthetic of a 2000s romantic comedy. Trios of young attendees danced happily on the deck, proving that romance in New York is less about finding a prince charming and more about falling in love with the collective choreography of urban survival.
Official Statements and Curatorial Vision
The philosophy underpinning Dream Baby Press is rooted in the reclamation of public and commercial space for artistic expression. In an exclusive statement regarding the curation of the "I Love New York" event, Matt Starr emphasized the importance of grounding literature in everyday life:
"We live in a city that tries its hardest to beat you down. Rent goes up, the subway breaks down, the algorithms try to dictate who you date and where you eat. Dream Baby Press is an antidote to that. We want to take literature out of the ivory tower and drag it through the greasy floorboards of a Sbarro or onto the deck of a 19th-century ship. When you put interesting people in strange rooms and ask them to tell the truth about how they survived this city, magic happens."
Comedian and entertainer Desus Nice encapsulated this sentiment during his reading, which served as the emotional climax of the evening. Recounting his return to New York after a temporary stint living in Los Angeles—the sun-drenched antithesis of the gritty metropolis—Desus described stepping out of a cab and feeling an immediate, visceral connection to his home turf.
As he walked down the sidewalk, a colossal New York rat darted directly across his bare feet.
"I didn’t scream, I didn’t yell," Desus told the captivated crowd, pausing for comedic effect. "I just said, ‘I’m home.’"
The line brought the audience to their feet. It was a joke, certainly, but it was also a profound psychological truth. New York is dirty, loud, aggressive, and expensive. It will break your heart, drain your bank account, and send rats scampering across your shoes. But for those who belong to it, there is simply no substitute.
Future Outlook: The Resurgence of Guerrilla Literary Culture
As the lights on the Seaport tall ship flickered off and the crowd slowly trickled out onto the cobblestone streets of lower Manhattan, the cultural ripple effects of the evening were palpable. The success of Dream Baby Press’s "I Love New York" event signals a broader trend within the contemporary arts and literary landscape: an abandonment of institutional gatekeeping in favor of immersive, community-driven happenings.
In an urban ecosystem increasingly threatened by corporate homogeneity—where local bodegas and independent bookstores are frequently replaced by chain pharmacies and luxury glass towers—guerrilla cultural programming acts as an act of urban preservation. By documenting the absurd, unvarnished realities of daily life, writers, comedians, and artists are actively building a living archive of New York City folklore.
Looking ahead, Dream Baby Press plans to expand its pop-up footprint, bringing its chaotic brand of literary performance to unexpected venues across all five boroughs. Whether staged in laundromats, subway cars, or historical landmarks, these events prove that as long as New York continues to produce broken appliances, billionaire benefactors, giant rats, and resilient dreamers, there will always be stories worth telling.
Ultimately, the evening proved that while living in New York can sometimes feel like starring in a low-budget, high-anxiety romantic comedy, it is a script that nobody in the audience would ever want to put down.
