The Bailers' Society

I have had a cough for a few weeks now. Early last week, the cough became a cold. My plans for the week fell through, and I actually had an excuse most people would understand. I felt a lot better on Saturday, and I relieved Meera of her caretaker duties before she departed that day for about a week home with her family in Massachusetts.

To avoid boredom and loneliness, I realized I needed to make plans. My journalistic ability to schedule has not failed me, and I created a robust social calendar within 30 minutes. What a joy to have friends nearby. I relish alone time, but if I am solo for too long, I begin to spiral. Bit of an ambivert. After a Saturday of wild walking before cozy friend hanging, I mentally prepared myself for what was to be a busy Sunday: lunch plans and dinner plans alike. Both of my friends bailed, but five minutes after my day fully opened, my friends Jordan and Jared called to coax me into spending yet another Sunday at Mister Sunday, an outdoor party at Bushwick club Nowadays I’ve talked about in past issues that is nearing its end before November.

Jordan, Jared, and other friends were waiting inside or coming shortly. I arrived alone in hopes of getting a ticket before they sold out, and the line was teeming with fellow losers. Shivering with their friends, all sorts of people chatted in line about other parties, being a gay woman in a gay male bar, and their friend’s new boyfriend (at least this is what I eavesdropped on). Standing alone in an all-black outfit during the day, some people would feel insecure waiting around while the people around them laugh with each other.

Instead, I was embarrassed because everyone just felt like posers. Mister Sunday is Bushwick Fashion Week, or at least Gentrifier Fashion Week. All types of clothes, hairstyles, and accessories. You’d think this means people are comfortable expressing who they are, and a lot of them are doing just that and look great. So many people just look phony! Most of the posers are men. They’re putting on a costume to fit in with their friends, the genders they’re attracted to, or with a version of themselves they want to be. Cool and clubby with a turbulent life. Maybe I hate them because I am one of them. But I chose my outfit because it made me feel confident. Well, I guess they did the same thing. It’s not like they’re looking in the mirror and thinking They’ll like me now. Or are they?

The way I find a poser is by seeing if they have College Boy Yearn Face, a term I just made up. I remember in my freshman year at BU seeing groups of boys walking around, whether in a dorm or to a party, and some of the men had a specific expression that is hard to define. It’s like their eyes are looking deep into their day’s future, imagining the shenanigans and maybe even sexual situations the night will bring forth. Part of it is a sense of wonder that they are in a group at all. This has nothing to do with how good their friends are to them; it’s more about knowing and looking like you’re in a posse. There is a vulnerability and an unsure look in their eyes. Although I first conceptualized this at university, I continue to see it, especially amongst groups of men outside of clubs like Nowadays.

I went into the club, and the disdain washed away as I danced and chatted. What a fun day to have that looked completely different than I assumed it would. This is due to New York City’s unique culture around making and canceling plans. When moving here, this was one of the biggest culture shocks I experienced. Making a plan was as easy as it was in college, especially as someone who can work from anywhere. People book their calendars far in advance but somehow have zero plans for the day you hit them up. It’s fate, and you have to hang. And when you do, it can feel like a fantasy. There is romance in the most grand and humble plans, and every moment spent with someone here feels like it matters. The people here are interesting and have differing life experiences you can observe through their verbal illustrations. Every hang is a treat.

Bailing on plans is just as easy as making them. This was where the real culture shock came in, and my day seemed ruined when someone would cancel on me. In the smaller places I’ve lived, my friends and I were much more consistent about sticking to premade plans. When I hit college and started having more friends and many who wanted to hang often, I wanted to be as consistent of an Omg yes! as I could be. I began expecting that from all of my friends, and people who could not be consistent would fall by the wayside. But now, how is everybody here like this?

Moving here and still learning how to use my wings, I would meticulously build skyscrapers of plans only to be knocked down by the real and fake excuses of others — and I was crushed under the rubble. I used to take bailing very personally because that’s not the kind of friend I wanted to be with others, especially when trying to foster new routines. But as I kept being a yes, I grew wearier. Hungover mornings at work or evenings I yearned for blankets and solitude kept piling on. After a few months, I started drowning in plans, and being the best version of myself for others did not provide any space for self-grace.

Somewhere in the heat of summer, I, too, became a bailer. A combination of moving, settling into a new neighborhood, doing all of this with a partner, and sun that propels you outside until you dry up gave me the security in myself to start saying no. I am still not a pro at this and do not plan on being one anytime soon, but I try to bow out respectfully.

There are two policies that I lead with: timeliness and honesty. As soon as I know that I’m a no, I let them know. Sometimes if I feel myself getting wishy-washy, I let them know, too. This allows them to have a sigh of relief and cancel or push me into socialization, which I oblige based on my mood. I am reminded of a once-viral New York Magazine modern etiquette guide published earlier this year, and one of them was You may callously cancel almost any plans up until 2 p.m. I agree wholeheartedly with this policy as it pertains to evening plans, as it allows the cancellee to mobilize a backup plan for their night. As for what I say when I cancel, I am sincere and I try to avoid lying. I hate when people create an excuse and I can tell. Instead of thinking you just want to watch a movie with your boyfriend, I’ll think you hate me and am waiting for me to stop trying to be your friend. Because of this, I’ll tell you if I’m just lazy and don’t want to leave the house. I’ll be sorry about it, but not sorry enough to sacrifice my time.

I have officially entered this bailers’ society, a group of robust 20-somethings that try to outrun their calendars when it’s too late. Now when someone bails on me, it is like a handshake, a contract we have signed that we can allow ourselves to be human and inconsistent. Obviously, if someone cancels consistently or invents excuses, this is different. But even good friends here bail, and I try to be a good friend. So I can bail now…and it says less about my friendship and more about myself.

This easygoing yet intense planning and bailing dynamic feeds into another core value of New York gentrifiers: individualism. Being the protagonist of our story is the vehicle of finding purpose in our lives. We all have multiple jobs because yearning is an extra gig we all pour energy towards. We yearn for connection but only on our own terms, vulnerable only when ready, feeling things when we feel like feeling them. We are incredibly open to experience but limited in our view of what that could mean. There is merit in this security, but we lose out on meeting our community where they are. We might be disappointing the millions not in the bailers’ society, especially if we pack this individualism elsewhere for those of us who travel and eventually move.

My friend Andje and I are members of the bailers’ society, whether we like it or not, and we usually don’t. I texted her Monday last week to see if she was busy and she luckily wasn’t. More of a walker than a runner, I met her physically (the Lower East Side) and she met me emotionally (wanting to take a long walk because I can’t be a runner girl like her). We walked along a track and path on the East River right near the Williamsburg Bridge. We swapped stories and giggles under the dark sky and bright buildings across the water. We walked next to Big Boo from Orange is the New Black (Lea DeLaria, and no I didn’t see her but Andje did), picked up a bizarre note someone dropped, and got hit on by the cashier at the original 7th Street Burger location.

The spontaneity we indulge in as new New Yorkers may lead to disappointment, but we chase the thrill of planning because of nights like these. One of the best qualities of this city is its ability to prove you wrong every day and show you something you didn’t expect. This is as whimsical as it is exhausting, so sometimes we need to take a night off — especially a night that was meant to be very much on.

Just moved to Boston and have a few days of pto / wanna use for a road trip nearby. Where should I go?

— New New Englander

Welcome to New England! Not that I can welcome you as I am not a native and no longer live there…but I still feel slight ownership. I’ve had my driver’s license since high school, but New England is where I learned to drive well and have fun doing it. It’s getting cold, but that shouldn’t stop you from seeing the beauty of the region. I’ll give you five places you can go.

Want advice from someone as unqualified but possibly more confident than you? Send in a question for Olympic Coaching.