For those reading this and wondering, “What is a hat box?,” “What is a Hat Box Night?,” or, “Why is this being revisited?,” I suggest you check out part one.
The short answer is Hat Box Night is an activity so epic it warranted not only a sequel, but also a threequel. (That's not a term but it should be, so consider it invented).
Hat Box Night is no ordinary evening—it’s a boundary-pushing, dare-filled social experiment that turns strangers into accomplices and bars into playgrounds.
Just like in the movies, a good sequel will find a way to bring the audience up-to-speed in-between installments, whether via on-the-nose dialogue, a quirky opening montage, or re-inserting the final five minutes of the first movie into the first five of the next. Real ones won’t need reminders; they’ve already held a marathon rewatch session featuring snacks and running commentary. But, I must humbly admit, not all my readers and listeners are so devoted that they have had the time or inclination to link-hop back to the story of the first Hat Box Night. And that is okay!
Here’s the deal: last March, my friends Erin, Annamarie, and I brought a 1950s-era hat box to Ray’s Bar in Greenpoint, Brooklyn. By the end of the night, we'd made new friends, broken down barriers, and created an unlikely posse that felt like peak NYC magic.
Afterward, I retired the box to a closet shelf, and the night lived in infamy as a Substack post. Life moved on: jobs changed, apartments swapped, marathons skated, relationships ebbed and flowed. The world turned, and the hat box gathered dust. I knew one day it would be pulled out of hiding, called into action like a superhero who absconded to Belize after a fateful battle with an enemy. When the time was right, the hat box would rise again.
It was early November when not one, but two friends went through break-ups of varying degrees of severity. This timing coincided with less-than-favorable election results and a drought in New York City, a place somewhat famous for its cinematic rain in the fall.
Vibes were off, morale was low, the world felt spooky, and the girls needed a night.
Hat Box Night: The Sequel
Like any good franchise, we embarked on our adventure by following a formula carefully crafted during Hat Box Night one. The first step was simple:
Acquire a hat box.
I pulled the box out and reminisced through old dares. Sifting through the slips, I felt like that old woman from Titanic looking at relics of her ill-fated Atlantic voyage. The memories came flooding back. “Ask a stranger for advice on something real.” “Improvise a choreographed dance.” “Convince someone you know them and double down on it.”
Needle drop; cue a song chorusing with energy and nostalgia.
We’re back in action.
Contact your most down friends. Invite them out for a night of shenanigans. Insist they wear their fun pants.
There’s something inherently more exciting about texting, “Should we have a Hat Box Night?” instead of, “Do you want to go out?” It’s like “U up?” vs “Hey I know it’s late but do you want to do a puzzle, have a drink, talk about our deepest desires and greatest fears and maybe even kiss?” Same idea, different approach.
The invites went out, and the Avengers assembled, ready for an evening that would live up to the lore of Substack post number 10.
Cut up slips of paper and grab pens. Stick ‘em in your purse and pockets.
I will be finding rouge pieces of paper in my purses, pants, and apartment for the rest of my life.
Go to dinner and brainstorm a few dares. This step is optional, but the mental pump-up pregame is mandatory.
Dinner was day-old salmon as my friend Danielle and I sat on the floor of my new abode (I had just moved and therefore not yet acquired a table or chairs or a couch), glasses of wine in hand, and began writing. Danielle, who’d moved to New York earlier this fall, was game for her first HBN, eager to take the city — or rather, Brooklyn’s quaint Cobble Hill — by storm.
Pick your destination. Choose a bar that’s not so loud that you can’t hear, not so packed that you can’t move, not so pretentious that you can’t play. Grab a seat.
We began at Congress Bar, allegedly a buzzing neighborhood spot. It was buzzing, for sure, but not at the same frequency as Ray’s back in March. This crowd was a bit tamer, more adult. You know the type — people who actually invest in a 401k and have a pesky back ache and are on a first-name basis with their butcher. While Ray’s had been packed with patrons ready to party, Congress was a collection of cool kids calling it a night at 10:00 pm.
By the time we got settled, our group had expanded to include friends Annamarie (a recurring character from last HBN), Maureen, and Jess. I wasn’t sure where we’d be more successful having a night out — Ray’s or Congress. Only one way to find out.
Write out as many “bar dares” as you can think of. Be creative.
The way Hat Box Night works is you fill the box with dares populated initially by the first group of participants. But the start was slow — too slow. We were writing; no one was biting. I was nervous. Were we coming up with the right dares? Were we doing enough? Maybe we needed to stop talking and just focus so we could have some fun. In hindsight, I hear it. “Focus so we can have some fun?” Ew.
Clearly I needed to let go of my expectations. If I didn’t loosen my grip on the whole thing, I’d suffocate the night. So the old rules went out the window. This Hat Box Night was going to be different than the one in March. I made peace with the present: it would be what would be.
But still, it would be fun if like, someone took the bait.
That someone was No Shot Sal*, an older gentleman with a fancy scarf and a stuffy attitude.
*Similar to last Hat Box Night I will be using pseudonyms, because they’re fun.
We presented our hat box filled with papers. No Shot Sal pulled out, “Ask someone their thoughts on the Wicked movie.” His brow furrowed. “But it hasn’t come out yet.” We consoled him, explaining someone could have thoughts on a movie even before its release. No Shot Sal couldn’t wrap his brain around this concept. He grabbed another slip. “Buy everyone shots!”
“Okay!” Sal agreed, then left. We never got our shots.
We did, however, make two new friends: the gregarious Upper West Wendy* and Just Left LA Lily*. They’d witnessed the Sal saga with wide eyes, wondering what on Earth was going on. Upper West Wendy pulled a slip. It was a classic: “Pretend you know someone and double down on it.” She walked over to a loner at the bar and we watched as she really, truly, desperately tried to convince him they had met. It didn’t work, but at least she tried.
Two strikes and it was time to move on from Congress Bar. Not that I cared — I was being chill, remember — but the problem was the place. As we plotted a secondary location, our group expanded: we were joined by friends Lexi and Ayla, and another recurring character: Tall Guy, first found during Hat Box Night one. He brought his friend, who we shall call Button Down Ben*.
We had high hopes for Talea, a brightly lit brewery down the street; it was about as bumping as a sheet of glass. Gathered around a long table, box in the center, down-to-clown Tall Guy grabbed a slip: “Ask someone their favorite song and sing it to them.” He approached someone who we will call HOW IS YOUR FIANCÉ* (this man had a fiancé and the group he was with made sure we knew) and started to sing. It was funny and sweet, a flicker of the game's original premise.
But that was the only one. The box got lost at the other table (the home of HOW IS YOUR FIANCÉ) where it was forgotten and shuffled around. After rescuing the hat box, it was time to move on… again. Our group, though smaller, remained determined. We would find our place.
We wandered like Goldilocks through South Brooklyn — Brooklyn Inn was too quiet, Public Records too pricey, but the Hollow Nickel, with its pickleback shots and unpretentious vibe, was just right. Sweet relief sank in as I settled into a seat and set the box on the table. The item of the eve was, “Challenge someone to a thumb war.” One valiant battle with Tall Guy later (he won), we called it a night.
The next morning, I sat on the floor of my apartment with a cup of coffee and looked over the unused slips. I’d promised an adventure but when the dust settled, all we had to show for the night were 10,000 steps and a bunch of blank paper.
Despite my fun night, I worried — I let everyone down? Had I failed my friends?
With a start, I knew the solution: we’d have to do it again.
Hat Box Night: The Threequel
One week later. Saturday in New York City and this time, I was going to get it right.
The issue was not the place, but rather the neighborhood. Cobble Hill, though lovely, is known for its booming population of babies and dogs. We needed to go where the young people were. We needed to go where the scene was. We needed to go to the Lower East Side.
I’d come prepared with a list of every potential bar in the area so we wouldn’t be a wandering crew carrying a hat box. We were going to have fun, dammit!
The night began again with Hat Box OG Annamarie. In the movie version of this story, she gets top billing and by the threequel, ideally a fat check. (For the record Annamarie is an amazing actress, so if anyone actually wants to make a movie adaptation of HBN, you need to cast her).
We convened at my apartment (which now had a table and chairs, but still no couch), before hopping on the train to Dimes Square, where we were met by friends Grayson and Anna.
For those thinking, “Do you mean Times Square? Copy edit your work, my God.” This is not a typo.
Dimes Square is a micro neighborhood between Chinatown and the Lower East Side that was established during covid as a hub for the internet’s coolest and grungiest writers, podcasters, artists, and scenesters. I think at one point Dimes was considered the 21st Century answer to the beat generation’s Tompkins Square Park / Greenwich Village. Allegedly the Kerouac and Ginsberg of the 2020s can be found smoking cigs and drinking natural wine on a car-free street between Delancey and Allen.
Dimes is also a hub for New York’s finest and frattiest. On any given night, the bars within the tiny geographic designation are packed and pushy and no one’s polite about their space. So obviously, it seemed like a good place for a good time.
We bopped. We hopped. We shopped. We could not get the bar right. Consider the following my guide for you: places to go (or perhaps to avoid) in Dimes Square.
In the summer, this restaurant spills out into the street, giving a certain Parisian quality. In the fall, or because outdoor dining has been shut down, Le Dive is confined to a tiny indoor space. It was packed by 9:00 pm. “Come back at 10,” the bouncer sternly announced, eyeing my hat box with genuine confusion and disdain.
It came recommended by friends who excel at going out. Unfortunately, it seems to be recommended to a lot of people. “We can put you in the sister restaurant until there’s room at the bar,” the hostess told us. She too looked curiously at my hat box.
To some, this is an indie movie theater known for playing films on 35 mm (a big deal for cinephiles). To others, this is a bar full of people who are really excited about movies on 35 mm. We got out of there before someone could tell me that my hat box reminded them of their favorite Frank Capra film that they would soon describe in detail.
More like ClandestiNO! This was the only place the hat box got some action but, much like dating a man in finance, it was quick and disappointing. Wall Street surfer bros Zyn Zach* and Juul Jack* pulled slips out, frowning as they struggled to read in the dim light. “Challenge someone to a thumb war?” “Ask someone their favorite color?” To Juul Jack’s credit, he tried. but the jam packed bar made it nearly impossible for a thumb war. “This is dumb.” The boys shoved their way back into the throng and we exited.
It was time to leave.
Walking down Essex Street, the box suddenly felt heavy. What had on previous nights been a delightful prop and conversation starter suddenly seemed cumbersome and stupid.
But we soldiered on, moving out of Dimes and up to the Lower East Side proper. Our destination was The Back Room, a prohibition era speakeasy (no, really, look it up) known for serving drinks in teacups. Surely this would be the right home for a hat box!
Womp womp. The bar’s two-story set-up and reserved tables meant holding the hat box with one hand and a teacup in the other. Once again, I found myself wanting to throw the box into a corner, to ditch the dang thing and be free. I was embarrassed, maybe even a bit sad.
“What is that!” We were stopped by a gaggle of girls in the alley on the way out of The Back Room. They gaped at the hat box. My heart soared.
“Want to do a dare?”
“Hell yes.” The girls pulled their slips out the hat box and read them, giggling. FINALLY! The moment was here, people were catching on, it was happening —
“HEY!” A bouncer in a fedora bustled towards us. “No standing in the alley. Get out. Go!”
“Maybe next time we do this, we won't bring the hat box.” I remarked to Annamarie as we wandered through the East Village later that night. We’d parted ways with our friends. “Maybe we just go out with the mentality and a few of our favorite dares instead?”
The heart of the hat box, we concluded, has nothing to do with a bulky vintage blue contraption. Sure, it’s a conversation starter. It removes a barrier. It gets you off your couch (if you have a couch). But it’s not entirely necessary. The important factor, what matters most, are the people you are with. Night after night, friends who love and care for each other participated, leaning in and saying yes to an objectively weird activity.
People want to be with each other, to be pushed, to have an excuse to go out and be silly. People want to show up.
Our evening ended at Amor y Amargo, a biters bar in the East Village. Danielle met us with her friend Molly. We didn’t touch the hat box. We had a great time anyway.
As I think about bar hopping and dating, I realize how the two are similar: both are hard to get right when you’re searching for something so specific. Instead of wandering for hours, maybe we’d be better off giving places and people more of a chance, even if one or the other doesn’t fit everything you’re looking for. Perhaps there’s something to leaning into imperfection, and discovering the good in what’s right in front of you. (Of course this doesn’t always work. Sometimes a bar can be really boring and a person can be really wrong).
There’s also a note about removing expectation from reality, how the most fun was when caution was thrown to the wind, and we followed each night wherever it went. HBN1 was a raucous round of dares at Ray’s. HBN2 was a slow burn with a big finish. HBN3 was for the girls.
Finally, before this movie smashes to black, credits roll, and you leave my little theater, the last lines offered are these: Hat Box Night was started and resurrected in honor and pursuit of friends. Time and time again, I’ve walked away from these evenings with a full heart, reminded how fortunate I am to be this age in this place with these people. Kind, brave, smart, fun, strange people. The pressure to provide a perfect party was self-inflicted, brought about from a desire to ensure everyone felt seen and that the night was worthwhile. But nothing is perfect, and everything is worth it if you just appreciate the moment, let go, and follow the fun.
For now, the hat box is back in my closet, where I assume it will stay for some time. Eventually, it will be needed again. But for what, who, or why? We’ll have to wait and see.
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