129 Ways To Get a Life
129 Ways To Get a Life (The Podcast!)
10. "Carry a Hat Box."

10. "Carry a Hat Box."

The story of Hat Box Night, aka the greatest Friday in recent memory.

My favorite New York nights are the ones where the parks buzz with picnickers, frisbee throwers, and people on blankets with their nose in a novel; the sidewalks bustle with outdoor diners and makeshift thrift shops; the streets teem with dog walkers, joggers, parents pushing strollers, and people like me – reveling in the magic of it all. Our story takes place on one of these evenings: a Friday in mid-March, the first beautiful spring weekend after a woefully wet winter. The sun is out and won’t be setting until 7:00pm and there’s a certain energy in the air, like anything can happen and everything is possible.  

It is a recipe for a perfect adventure. In my case, that was Hat Box Night – the first of its kind, but hopefully not the last. Necessity is the mother of invention, and in this situation we have list item #10. “Carry a Hat Box” to thank for what has become one of my favorite evenings, and activities, in recent memory. 

So without further ado… this is the story of Hat Box Night.

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1. Acquire a hat box. 

Step 1 was relatively easy. Back when I was in high school, my mother inexplicably brought home not one, but two vintage hat boxes. I think she’d found them at a garage sale and thought I might have a use for them. She was right, even if it took ten years to identify the proper project. 

2. Text your most down friends. Invite them out for a night of shenanigans. Insist they wear their fun pants. 

This is where I write a love letter to Erin and Annamarie, the girlfriends who heard my pitch for a night of “hat box related weirdness” and blindly said yes. 

3. Cut up slips of paper and grab pens. Stick ‘em in your purse and pockets.

I thought 40 slips would be enough; I was sorely mistaken. 

4. Go to dinner and brainstorm a few dares. This step is optional, but the mental pump up pregame is mandatory.

My roommates and I wrote out initial ideas over martinis (gin, dirty, espresso) and mozz sticks at Bernie’s, a trendy Brooklyn neighborhood hot spot masquerading as an old-school style American joint. 

Early slips included: 

  • Ask someone for their email 

  • Send someone soup (a nod to Randa and Harry, see Item #9

  • Get someone to buy you a drink 

  • Use an Australian accent for at least 10 minutes 

5. 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.

I wandered across a picture-perfect McCarren Park to Ray’s, the Brooklyn offshoot of a popular Lower East Side bar. Ironically, another hip locale pretending to be a divey pool and BBQ saloon, Ray’s occupies a corner of Greenpoint that is known to locals as “cursed.” The building is a revolving door of real estate; it seems no restaurant can manage to stay open for more than a year. This latest addition has brought intrigue to the area as passersby wonder if Ray’s will be the bar to break the curse. Only time will tell, but I can promise that on this particular Friday night, we did our part to help it stay open.  

6. Write out as many “bar dares” as you can think of. Be creative. 

Inside Ray’s, I was met by Annamarie, one of my favorite people and my first roommate when I moved to New York. Annamarie and I lived together for three months in an Upper West Side apartment that can at best be described as “sort of legal.” She slept in a loft bed an inch from the ceiling and I slept in a twin bed in the “living room.” It was chaotic perfection. 

We spent the first thirty minutes of the night catching up at a table across from the bar, the hat box placed awkwardly between us. The idea was to have one drink and write out a few more slips before we really jumped into action. Though I didn’t vocalize it, I was worried. What was the plan, exactly? 

At this point, Hat Box Night was a half-baked notion inspired by a Girls Night Out and a list item (#10) which read, “Carry a Hat Box.” My thought was to bring the hat box from bar to bar, randomly picking and acting out tasks, hoping someone would talk to us. I figured the hat box would be enough and folks would line up to investigate the strange round cardboard contraption. I was wrong. Thus far, all it had warranted were a few curious stares and an annoyed huff when it took up too much room on the table.

Annamarie and I finished our drinks, still waiting for something to happen. 

And as the barback – let’s call him BB, Barback Barry* – came by to clear our cups, a lightbulb flickered on. We went through the effort of bringing a hat box to a bar, writing dares on slips, buying drinks, and we were waiting for something to happen? No way! Nothing fun comes from sitting around hoping adventure will occur. You have to make it yourself. 

As BB went to pick up our glasses, we thrust the hat box in his face. “Pick one!”

*to protect the innocent, and because I didn't get explicit consent to use their names, we'll be having fun with pseudonyms today. 

7. Stick your hand in the hat box and pull a slip out. Read it. 

BB looked at us, bewildered and bemused. Then to our delight, he obliged. Holding the dish bin in one hand and a paper slip in the other, BB smirked as he opened his slip. “Improvise a choreographed dance.” 

8. Let the games begin. 

His face fell. BB sighed, frowning. “I can’t do this.” We proceeded to encourage him. “Yes, you can! You can do anything!” 

“No really,” he shot back. “There’s not enough room for me to dance. I can’t create in these conditions.” His fellow barback – Coworker Carl* – joined the fray as we tried to get him in on the game. Carl had the same response. I guess people need a lot of room when it comes to creating a masterpiece with their feet. 

BB and Carl shuffled off, blissfully unaware of the evening that they had just set into motion by taking a slip out of the hat box. The first string in the Rube Goldberg Machine had been pulled, and the chain-link reaction was inevitable. 

Behind the barbacks, two intrigued men had been eyeing the interaction. These are the guys who really deserve the credit for making the night the hit it became. We’ll call them The Originals (OG1 and OG2). Annamarie and I asked if they wanted to play. Or maybe they asked what we were doing. Regardless, before we knew it, our new friends OG1 and OG2 had pulled dares out of the box. 

OG1: “Tell someone their shoe is untied when it isn’t.” 

OG2: “Ask someone for a celeb shot at the pool table.” 

They read their tasks and laughed. OG1 retorted with a question. “What do we get for completing it?” Understandably, as we live in a quid-pro-quo society, I guess even a bar game requires some back scratching. 

So this is where the first in-action rule of Hat Box Night came to be. 

8. You can write a dare after you do a dare.

OG1 walked over to the bar and told a girl in loafers that her shoe was untied. He returned to our corner giggling. “That did not go over well.” But still, he did it. As OG2 worked up the courage to interrupt a (probably expensive) pool game, the boys wrote out their dares and the four of us began chatting. 

Three new ideas were tossed into the box: “Tell someone you recognize them from Hinge,” “Ask someone the last place they’ve traveled,” and “Ask someone for advice about something real.” 

OG2 marched over to the pool table and requested his celeb shot. He soon returned, laughing and red faced. “That also did not go over well.” Knowing nothing about OG2’s pool skills, I feel confident saying it was their loss at the pool table. He could have won those players the game. 

“We need more people to get involved,” OG1 announced. Though impressed by his commitment and his investment in the evening, I nervously cringed when he tapped the group of girls behind him and invited them to play. But to my delight… they couldn’t have been more into it. 

The gaggle of six gals passed the box around their circle, tentatively sticking their hand in the Pandora’s Hat Box, unsure what would be released from within. 

“Ask someone for their email,” Email Ellie* sputtered, cackling as she read the dare. She shrugged. “If it helps me meet my husband, why not?” 

“Get someone to buy you a drink,” Not Single Sally* announced, grinning from ear-to-ear. “Sure, why not?” She headed over to the bar and tapped the first girl she saw. 

“I can’t do that. Or that. Or…” This was Debbie Dare*, who plucked item after item, grimacing after each, not ready to do the tasks at hand. “Can I write one out instead?” We acquiesced and made an exception. Good that we did — Debbie Dare would go on to write some of the wildest slips of the night. One of her best was, “Ask a stranger for their chapstick. And even maybe a smooch!” 

Soon, three other central characters joined us. My best friend Erin entered just in time to add her secret sauce of charm and fun. Then came along the Greenpoint Guys – Guernsey and Calyer, we’ll call them. 

Guernsey: “Convince someone you know them and double down on it.” 

Calyer: “Ask someone for advice about something real.” 

Guernsey shot off to another end of the bar and before we knew it, he was chatting up some tall guy, who for the purposes of this piece, will be called Tall Guy. We watched as the two men interacted and potentially became best friends. Meanwhile, in our little corner of the world, Calyer was thinking hard about the advice he needed. What transpired was a very honest conversation about his upcoming wedding and some concerns he had regarding the guest list. “Wow,” Calyer remarked after Erin, Annamarie, and I finished sharing our thoughts on the matter. “I really needed this.” 

The heartfelt moment was interrupted by the return of Guernsey and Tall Guy, “friends from camp in Michigan,” a convincing lie that took me half the night to realize was part of the bit. Quite embarrassing considering I was the one who wrote out the dare. 

Regardless, Tall Guy and his friend (Manhattan Max*) soon joined the fray, bringing our once small posse to 15. To my utter amazement and absolute delight, at this point, everyone was in on the game with no signs of slowing down. We were collecting players faster than an NBA team during the big draft (I have no idea if this is how the draft works, but since it’s March Madness, it feels topical). 

To write out the rest of the evening is a Herculean task. And frankly, I don’t think I could do the magic of the night justice. I could give a play-by-play of the people we met, the conversations we had, the shots we took, but honestly it was such a joyful blur of chaos and new friends and laughter and awkwardness that I think the best summary I can share is via the notes app diary I scribbled at 2 a.m., moments before my happy head hit the pillow. 

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  • Debbie Dare not wanting to do any items but writing the most insane shit you’ve ever read

  • The girl who was like, “Yeah no problem I’ll go pick up the pool cue and move it but we will have to promptly leave the bar after”

  • Girl who asked the bartender for a spare condom (he didn’t have it) 

  • Annamarie and Erin being the most supportive, wonderful friends ever 

  • The guys who wrote “go home” and “commit arson” as their dares (woof!!)

  • OG1 pushing for other people to get involved 

  • The girl who didn’t know how to cut things off with a guy she was seeing so she instead asked a random girl for advice 

  • The girl who brought me a glass of water (her item was to hand someone water, iconic dare)

  • Guernsey telling me about a random underground party on a LIC high line (have the LinkedIn screenshot for the guy who runs it, check photos)

    • Also, is there a High Line in Long Island City? 

  • Learning that CIA training requires you to get a stranger to buy you a coffee

  • Strangers becoming friends!!!  

  • Creating a weird mini impromptu community 

  • Low key running Ray’s 

  • Seeing how many people were down to play and wanting to meet new people 

  • Manhattan Max getting “Ask a stranger to borrow their chapstick,” DOING IT

  • The girl who pulled out “Eat this paper,” and no questions asked, ate the paper and chased it with a swig of beer 

  • Disappointed no one sent someone bar snacks or soup  

  • Annamarie + Tall Guy thumb war 

  • The amount of people who were like, “How often do you do this?”

  • I’m going to trademark hat box night

    • Should I become a CEO? Tbd, figure out in the morning

      • Or go on shark tank to sell this as a kit ? yes def trademarking  

  • Girl that took a selfie and posted it to IG 

  • Learning how planes are refueled mid-flight 

  • Australian accents are so much fun we should use them always 


  • New York is so cool people are so cool wtf i love it here :) 

The next morning, I woke up beaming. Still floating from the high of the night before, I grabbed a bagel and sat in the park, basking in another beautiful spring day, giggling my way through my camera roll. It was packed with photos of strangers holding slips of paper, visions in red highlighted by the dirty neon lighting at Ray’s. I sorted through my hat box, reading through the items we never got to and reflecting on the ones we did. I texted the number on the slip which read “are you hot? are you funny? are you single?” 

I asked Erin and Annamarie for their recap of the evening. 

Annamarie: “I think what was so cool about it was it really brought so many people in a very surprising way. There were definitely some cool Brooklyn girls there and I know where I stand, I don’t have a leather jacket, they thought they were so cool. And then this hat box… they were putting in suggestions, pulling things out! I thought that was also really cool, was it brought people together as friends as well. I know it came from a list of how to get a significant other but those guys that became friends didn’t know each other, a bunch of those girls I think didn’t know each other, WE didn’t know them. It was an incredibly unifying presence inside of Nicholas Braun’s cool bar. I feel like sometimes you want to do these fun silly things at bars but you’re a little scared to and this was like, “I have to, the hat box said it!” Anyways. Hat box night for life.”  

Erin: “Hat box night was one of those favorite nights you have. You have nights that go down in your memories forever. It was the first time in a while where I feel like I actually met new people. We had a whole bar of people who are actually interested and making new friends and getting to know each other. People always talk about how difficult it is to meet people in NYC. However, hat box night illustrated that if you’re just daring enough, just confident enough, just silly enough, you can leave a night out with 25 new friends. too often, we stay in the bubbles we know, but if we put ourselves out there more, great things can happen.”

And then I thought about mine. How would I explain Hat Box Night to my younger self? What would I tell her about the evening that felt like New York in a nutshell? 

I’d probably say how lucky I felt the next day. Not only because the evening was weird and wonderful and silly, but also because of the friends which made it so special. In life, we get the privilege of picking our people. We get to surround ourselves with folks who make our world better. Without good friends, Hat Box Night would not have been what it was.

So yes, sure, the fun of the night was that we met so many wonderful folks. We were reminded that people do want to meet in real life and they want to engage at a bar. We made the bar fun again! We walked away with phone numbers and fun facts and new Substack subscribers (hello, pals!). But the heart of the night – the memory I will hold on to, the story I would tell my younger self – rests in the fact that my friends showed up in a big way. 

Cherish your people. 

And if you can get your hands on a hat box, go out and have a night. Who knows what’ll happen. 

Thank you for reading 129 Ways To Get a Life. This post is public so feel free to share it.


129 Ways To Get a Life
129 Ways To Get a Life (The Podcast!)
A series in which a 20-something exclusively follows the advice of a dating column published in 1958 to explore modern love and life.