The Experiment: Can a Serial Planner Enjoy Spontaneity?

240703 D1 A RESTAURANTHEADER 2
  • Text Sinead Chang
  • Design John Portis

My iPhone screen time is steadily climbing up, and no, it’s not because of my nightly doom scroll. On the contrary, I blame this increased time spent on my phone on a desire to get off of it: to sing at the top of my lungs, to shut off my small screen in favor of a big one and to split an order of fries with all my best friends. But, it feels like in order to find the joy of IRL connection, I have to hit refresh over and over again, battle the bots and plan far out in advance, whether it's for a once-in-a-lifetime concert experience or a dinner out at a trendy restaurant. Even movie tickets now require advanced planning. This all begs the question, whatever happened to spontaneity, last minute plans and exploration?

I’m the most guilty of refusing to eat out without a reservation, so for this experiment I, a brave Gen Z serial planner, went on a Saturday Girls’ Night Out with two of my friends, Anika and Devon, to investigate unplanned dining and unlearn my toxic relationship with needing to have everything mapped out. I wanted to find out what a night out in the West Village—a neighborhood with notoriously hard-to-get-into restaurants—would look like with no reservations.

Screenshot 2024 07 08 at 2 35 12 PM

Anika lives in the West Village and had told me previously that if she doesn’t have something booked, she doesn’t go out to eat in her neighborhood. Devon is apathetic towards dining out and probably couldn’t name a single West Village restaurant. The three of us used to dine on cafeteria food together every lunch back in high school, but it had been a minute since we last shared a meal.

Going into Saturday, the question was: Would we finally be eating at Don Angie, a restaurant I’ve tried and failed to get a reservation at for years? Or, would we be eating pizza on the floor of Anika’s apartment? The lack of a plan was stressing me out, and I felt responsible if my friends had a terrible time.

The Waitlist

At 6 p.m., I put on my new pink skirt and hopped on the subway. As luck would have it, the weather was perfect that day—the best of summer in the city. Patrons spilled out of every restaurant and bar I walked past, aperol spritzes in hand. The West Village was packed.

Half an hour later, I was standing at the corner of Grove Street and 7th Avenue, observing Bar Pisellino’s sidewalk line. (Not surprising, given their viral aperol spritzes). Once Anika arrived, we crossed the street and I gave my number to the host at Via Carota, an Italian restaurant most recently known for being one of Taylor Swift’s go-to spots. It’s virtually impossible to book a table there online, and we were ready to wait. The host quoted us three hours, meaning that we’d be seated at around 9:30 p.m. Ever-so-optimistic, Anika and I agreed that it didn’t sound that bad.

Resturant Article asset 1

I’d like to think that I’m above going places just because everyone else is talking about them on TikTok, but I’ll admit that I Sodi and Don Angie, two upscale Italian restaurants, were next on my list. The former had filled their walk-in list for parties larger than two for the night, so we turned to the latter. With my best smile and hiding my underarm sweat stains, I confidently asked the host at Don Angie if they had any more space for walk-ins and was pleasantly surprised when she told us that while the waitlist list had filled up, we could be put on a list for cancellations.

Finally, Anika suggested American Bar, a restaurant I frequent that always reminds me of what I think a country club would be like. Though I worried we’d be seated immediately based on past experience—and we were still waiting for Devon—the line of people spilling out from beneath the dark green awning and onto the sidewalk dispelled my concerns, as did the three-hour wait. Anika gave the host her number, and it was time to play the waiting game…

Resturant Article asset 2


The Waiting

The part of the night I was most looking forward to was the waiting: I had an idyllic picture in my head of the three of us sitting on metal folding chairs on the sidewalk, ice-cold drinks in hand. How hard could it be to get into a bar in a neighborhood where there’s one on every corner? (Hard, it turns out.)

Anika and I started walking towards Buvette, a French restaurant and bar, alongside a group of four girls dressed in a matching color palette of black and white. It seemed like they were in a similar situation, discussing where they could go for a seat and a drink. We quickened our pace, and I nearly ran into a blonde ponytail when the group stopped in front of Buvette to ask for a table. They left when the host said it would be a few hours wait.

When it was our turn, the host said that they could squeeze us in at the bar soon if we waited on the sidewalk. Not yet realizing that we couldn’t afford to be picky, we left, hoping for a table with a view somewhere else.

We raced the same group of girls down Bleeker Street to the one empty table at St. Jardim, but it didn’t matter. A very harried server informed us that they were only seating people for dinner, not drinks.

Resturant Article asset 3

Defeated, Anika and I decided to return to Bar Pisellino, where I had started this whole adventure. The line, which was already terrifyingly long, seemed to have doubled in size. Having found no better place to wait, however, we decided to linger while we waited for Devon.

The Eating

At 7:26 p.m., 20 minutes after Anika got a confirmation text from American Bar saying that she had been added to the waitlist, she got another text: our table was ready, and it would be held for us for 10 minutes. With an eye out for Devon, we weighed our options: eat at American Bar immediately or wait two more hours for Via Carota, a restaurant that was undeniably more clouty. (I mean, Taylor Swift!) We were pretty excited about Via Carota, so we decided that we could continue to kill time by waiting for and then drinking at Bar Pisellino.

A few minutes later, Devon arrived, notably wearing an I Love NY t-shirt. (She was coming from a New York themed birthday party.) After explaining the situation, Devon pulled us out of our delusion: she was hungry and content to go to American Bar. Suddenly, I saw our situation in a new light: why did Anika and I want to go to Via Carota so badly? All that mattered was that the three of us would get to have a nice dinner together, so American Bar it was.

Resturant Article asset 4

It was now 7:32 p.m. and we were a six minute walk away from American Bar. If they were strict about our arrival time, they’d be giving the table away to the next party in line at 7:36 p.m. We took off running.

Putting aside the stress of whether or not we’d make it in time to claim our table, there was something magical about running down the street whooping and hollering and giggling with two friends I grew up with. I can’t remember the last time I embraced the frenetic joy of being alive in this big, big city and let go of the ringing and pinging of alarms and alerts. It was an epic culmination of the evening’s experiment, a metaphorical shaking up and resetting of my obsessive dining planning. It was a reminder that eating out, like the rest of life, is really about the joy of being with other people. The rest is just background noise.

American Bar seated us right away. We discussed the gossip that our friend had texted us from the high school reunion that we missed the night before, sipped on palomas and snacked on onion strings. I paid $27 for the TikTok-viral peanut chicken salad for dinner—at least some part of my night had to be on trend—and unfortunately, it was worth the price. In the dark interior of the dining room, I could barely make out the faces of the diners around me, but the candle on our table illuminated our conversations like a campfire, and that was more than enough for me. I sunk into the plush booth, and the stress of the waitlists melted away. This is what eating out with friends ought to be like.

Resturant Article asset 5

We walked out of American Bar at 9 p.m., and Anika and Devon repeatedly emphasized what a wonderful time they’d had, even just running around. We learned it’s much easier than we thought to eat at Via Carota, and while it’s great to have the assurance of a confirmed table at a hot new restaurant, we could definitely embrace spontaneity again sometime soon. Life is too short to be spent constantly planning ahead: I’ll continue to find my way into all of the restaurants on my ever-growing list, but perhaps with a little less screen time and a little more stopping by.