The lost art of being a regular
Online reservations, social-media hype, around-the-block lines, delivery apps – have drinking and dining always been this isolating?
ON A MONDAY in June, like almost every Monday for the past two years, my brother and I walk into Gertrude’s, a bar and bistro at the corner of Carlton and St. Mark’s in Brooklyn. The evening air sways through the covered patio, where the general manager greets us with a smile while sporting a striped party hat – it is, after all, Gertrude’s third-birthday party.
Inside, it’s already buzzing. Whitefish croquettes are shuffled from the kitchen as freshly filled Nick and Nora glasses leave the bar. Balloons bounce on the ceiling, blown around by the air conditioner; someone turns up the stereo. The shelves behind the bar, lined with wooden and rubber ducks of all varieties, are trimmed with rainbow garland. As we settle onto our stools, we’re suddenly congratulated by one of the owners – it is, as it happens, our hundredth visit, or as one server puts it, our centennial.
“This is actually all for you,” quips the director of operations.
When Gertrude’s opened in our neighbourhood, my brother and I made it a point to show up as often as we could. We wanted to support the new spot, of course, but the goal was to become familiar enough that we could always, or almost always, get a spot at the bar. Through sheer repetition and recognition, we’d have a place that wasn’t our apartment where we could get a drink without having to mix it ourselves. The food was unpretentious and delicious, the martinis were freezing cold, and the music was an excellent mix of ’80s pop and ’00s indie. In an area lacking fin(er) dining and relatively kid-free establishments, Gertrude’s checked several boxes. The only question was when we’d go.
Our weekends were crowded with errands and extracurriculars, and there wasn’t a single weekday that felt more special or available than the next. So when Gertrude’s announced a new weekly special – every Monday, its signature burger would get remixed either in-house or by a guest chef – it felt like kismet.
At first, it was a joke between the two of us: The Burger brothers attend burger night. After a few weeks, however, the staff started to notice our continued presence, and they got to know us. Yes, we’re actually brothers. Yes, our last name is actually Burger. Our reputation often precedes us, but every now and then, we’ll meet someone new from the back of the house who inevitably chimes with sudden clarity, “So you’re the Burger brothers.” That’s how we know we’re something that’s not so common anymore, something lost in a world of delivery apps, online reservations, social-media hype, and around-the-block lines: My brother and I are regulars.
ANY self-respecting, occasionally indulgent adult should have a standing reservation at a favourite spot. The New York dining scene, like that of many cities in the U.S., is vast and roiling. In a matter of months, new places open, thrive, peter out, and close. Not only does being a regular simplify your nights out; it also supports the restaurants and bars you love. It’s hardly a good alternative to try to land the right Resy at the right place at the right time or schlep around on an empty stomach, crossing your fingers for a walk-in spot only to wait 45 minutes for a table.
Being a regular shapes my weeks because I know that something enjoyable is always on the horizon. Though we live together, my brother and I don’t always have the time to properly catch up. A couple of hours at Gertrude’s – out of the house, away from computers, TV, and other distractions – gives us a chance to chat about the weekend, plot the week ahead, or simply yap. We people-watch, shoot the shit with the bartender, and meet new neighbours. It’s not about alchemising the most TikTokable moment but rather slipping into the comforting lull of familiarity created over the course of many, many visits.
Now when we walk in, the bartenders know we like to start with martinis and that we can often be persuaded into an after-dinner amaro. Sometimes we’re guinea pigs for new cocktails or treated to duplicate orders of spaetzle or latkes from the kitchen. Our presence has become so expected that it’s not uncommon for us to flag the staff ahead of time if we’re going out of town.
Over time, mundane events become memories: Someone’s first or last day on the job, a shipping mix-up that inflates the typical matchstick fries into steak fries, the night when leftover Jell-O shots from a Pride party cap every meal, that dinner rush when the Toast point-of-sale system fails so receipts are tallied by hand. You learn not just the names of the staff but their birthdays, hometowns, preferred train lines. If you’re lucky, you meet the chefs, dishwashers, bussers, and all the other hands working tirelessly, invisibly, to keep the night going. Over time, you too become a fixture, always expected and always welcomed. As Detroit-based bartender Abigail Jennings puts it, regulars “help define” their favourite establishment.
At Gertrude’s, I’ve gotten to know a group of people I might never see outside the walls of the restaurant. It’s community building in the most basic sense – it’s not home, it’s not work, and while it’s not necessarily private, it’s an experience I opt into. In a time when we’re constantly, if subconsciously, self-selecting our worldview and algorithm into hyper-personalised bubbles, getting to know someone who’s not your age, who’s not in your tax bracket, who doesn’t live in the same corner of the Internet as you – that’s needed now more than ever.
I’ve also found that being a regular is one of the best ways to hear local news. What new restaurant is moving in where, who just got their liquor license, whose backyard is underrated? With so much of our modern social life funnelled through frictionless, abstract interaction, neighbourly gossip is a godsend.
BECOMING a regular necessitates repeated visits, but how often is enough?
“A couple times a week, a combination of weekday and weekend, I could see you as a regular,” says Lauren Rojas, bartender at Jac’s on Bond in New York.
The process of becoming a regular varies, however. Your status begins and ends with, well, you. If you like the vibe of a certain spot, try going on a slower day. Places need to make money on Tuesdays as much as Fridays, and not only are you more likely to get a seat, but you’ll probably have more opportunities to get to know the staff.
Of course, showing up is only half the story. The easiest way to make a good impression? Sit at the bar and get off your phone. You should be ready and willing to get good at small talk. Introduce yourself – more than once, if you have to. Chat up the bartender or server when you can, knowing they’ll likely have to pop in and out. If you haven’t had to bridge the gap between complete stranger and friendly acquaintance since kindergarten, treat this as a useful refresher. It’s not about schmoozing, though.
“You can’t just come in and want to be my best friend – sometimes that comes off as really creepy. If your bartender just wants to be your bartender that day, you don’t have to be buddies,” says Jennings.
Part of what makes a good regular, says Jessica Foster, a bartender at Bumbo’s Bar in Detroit, is “interacting with people who aren’t the people you came with, being a part of the community of the bar.” The person next to you might not become your best friend, but you already have one thing in common. Therefore, you have to invest in the space – literally. If you go into a bar or a restaurant with hopes of getting something for free, you’re doing it wrong.
“My mindset is always that I’m happy to be there and happy to pay for everything, and anything extra is just a bonus,” Jennings says of being a regular herself. “I usually end up giving it back in tip anyway.”
As much as the staff is working to provide a satisfying experience, so too must you be a willing and gracious guest—not simply reveling in the ambience but helping uphold it. No matter how comfortable you might soon become, it’s still someone’s place of work.
“It’s natural that the more something feels like home, to treat it like your house – you’re not going to leave a mess behind you,” says Jennings. “There’s a little bit of responsibility with anything you reap extra benefits from.”
Jennings notes that regulars are not only friendly faces but also a reliable means of support. If she has to pull her attention away from the room for whatever reason, knowing that there’s a handful of people who have her back is a relief. Unsurprisingly, the qualities that make a good person make a good regular.
“Be nice, kind, gracious, patient. A sense of humor is always welcome,” says Rojas, “and a good tip.”
BEING a regular starts in one physical place but, if you’re lucky, extends beyond it. The success of Gertrude’s recently led its team to open a new spot, Trudie’s Tavern, where my brother and I were invited for a friends-and-family preview. We sat at the bar, per usual, and scanned the new menu, comparing and contrasting it with the one we see every week. Since it was the same night as game five of the 2026 NBA Finals, we bemoaned what would obviously become a futile search for a watch party elsewhere—until someone taped a tablecloth to one of the walls and busted out a projector. One of the owners, a lifelong Knicks fan, waited until the third quarter to turn on the sound.
By the final minutes of the game, most people had filtered out, while a few—the true friends, the literal family, and us – hovered around the projection together. The final buzzer rang out and the room erupted as the New York Knicks won their first championship title in more than 50 years. We hugged and high-fived strangers and floated outside, where the streets filled with cheers, car horns, and orange-and-blue jerseys. I don’t think we ever said goodbye to anyone, but it didn’t matter. We’d see them next week.
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