WASHINGTON, D.C.
October 21, 2025

STRANGER: Jeb Brooks
LOCATION: Filomena, 1063 Wisconsin Avenue NW, Washington, D.C.
THEME: Creating a YouTube hit about globetrotting adventures

For someone who spends half his time traveling the world on planes, trains and buses, Jeb Brooks carries himself with a peppy energy that makes you think he’s never heard of jet lag.

He meets me for dinner with a broad smile and natural enthusiasm that’ll be instantly familiar to any of the almost one million people who follow his globetrotting adventures on YouTube. That’s the home of his channel “Greener Grass,” charting travels with his wife Suzanne to and from locations as exotic and far-flung as the South Pole, Madagascar and Newark, New Jersey.

We’re dining at Filomena, an old-school institution in Washington D.C.’s Georgetown neighborhood. I didn’t realize when pitching the place for our interview, but it’s just a short walk from Jeb’s home. He and Suzanne moved to the District to take advantage of its great airport connections, making it even easier to travel and film videos for their channel.

Inside, Filomena looks like old-world Italy on overdrive: latticework panels, enormous floral urns, and a riot of reds and greens straight out of a Venetian postcard — all currently sharing space ahead of Halloween with skeletons and ghouls hanging from the rafters. It’s as if Jack Skellington were let loose in an Italian piazza.

As for Jeb, his appearance is far more restrained than the restaurant’s. He’s impeccably turned out in a well-fitted navy suit, a patterned shirt, and the calm confidence of someone who might consider an airport lounge to be his second home. His expressive features are framed by neatly trimmed salt-and-pepper hair and beard. He looks so dapper that if I were a gate agent, I’d give him a free upgrade to first class.

Our choice of an Italian restaurant for the dinner interview leads naturally into Jeb telling me about one year when it seemed like he and Suzanne were in Venice every other month.

“Tough life,” he says with a knowing laugh. “It has its charms.”

When we meet, that life on the road had most recently taken them to Athens. They flew one leg on United and the other on Emirates, first class for both. “We wanted to compare these two to ask the question: Are U.S. airlines really as bad as people love to say they are?”

In that video, you can learn what lures viewers in and keeps them engaged for the almost 25-minute travelogue (at the time of writing, over 230,000 people have watched it). Jeb and Suzanne walk through every aspect of the journey, starting with the airport arrival and visiting the United lounge, sampling the food and drink and showing what to expect from the furniture, other perks and more. Then onto boarding the aircraft, and here’s a small but telling example of the honest way Greener Grass operates: Jeb expresses mild frustration with a flight attendant blocking his seat while arguing with another passenger.

But that doesn’t dampen his enthusiasm for showing viewers around his seat, reviewing the in-flight food and other services. And they are thorough, one example being the tape measures they carry for sizing up seats, television screens and other features to see if they match what airlines claim publicly. For the return leg, it’s the same approach.

The video wraps with ratings for key factors — price, service, food, in-flight entertainment — and, finally, a ‘Jebscore’ deciding whether Emirates or United comes out on top. I’ll let you watch the video to find out, but stick around at the end for some charming bloopers.

Jeb says the idea for the video came about in part through the active comment section on their channel, reading people’s remarks about how U.S. airlines fall far short of the quality set by competitors overseas. He says a follow-up trip will test what it’s like flying economy from New York to London on the major U.S. airlines American, Delta, JetBlue and United.

“Coming up with the idea is probably the hardest for two reasons,” Jeb says. “First of all, the creativity side of this challenge. It’s rewarding, but challenging. And then the other thing is making these trips all fit together. The airline schedule, the hotel availability, we try to use credit card points. So that’s another factor that layers into the complexity of these things, which is really where Suzanne shines. These are complicated problems she’s solving.”

Jeb hadn’t met Suzanne when he first started making travel videos, so in those early days he handled all that problem-solving solo.

Even before YouTube, though, there was always what he calls “an obscure interest” in aircraft. “It was always a hobby but never seen as cool, not something to pursue a career in,” he says.

He grew up in Greensboro, North Carolina, then went to Washington and Lee University in Virginia, studying sociology and anthropology.

“What made you choose that?” I ask.

“It was easy,” he says, laughing. Then – in a style I’ll learn throughout dinner is naturally his – he follows the quip earnestly: “I’ve always been fascinated by how people interact.”

Our cocktails arrive, an Old Fashioned for him, a Manhattan for me, and we cheers.

“To strangers and friends,” he says.

A plate of arancini lands between us, two large, round crisp golden shells giving way to soft, molten rice. They’re made with Arborio rice, stuffed with mozzarella, Bolognese meat and tiny peas, then rolled in breadcrumbs before frying. The delectable orbs come with a trough’s worth of zippy Sunday sauce, making for an excellent starter.

Between bites and sips, Jeb peppers me with questions about Dining With Strangers, my life story and more, that natural interest in others coming through. But he’s the one being interviewed, so eventually I shift the focus back to quizzing him.

After graduating, he moved to Phoenix, Arizona, to work for a human resources company, focusing on leadership training involving psychological assessments. But the brutal desert heat made him realize he wasn’t long for living there, so he moved back to North Carolina. And that’s when he started working for his father’s sales training company.

Still unsure of his long-term plans, Jeb signed up for law school, although this also wasn’t the greener grass he was looking for. “The summer after my second year I worked for a law firm and it was clear to them and me that this was not the path for me. There’s a detail orientation that one would expect from a lawyer. I spent the entire summer on one memo.”

His dean encouraged Jeb to complete the degree, and he did. By this time, his father had passed, and Jeb was still working for the sales company. One of many life pivots he took, looking for the greener grass whether it’s careers, a place to live, or anything else.

The job involved extensive travel, and while on the go he’d watch YouTube channels of people filming trips around the world. He realized that nobody had made a video about something he wanted to see – first class on Air France’s A380 from D.C. to Porto, Portugal.

In 2015, he had to attend a work conference in Portugal. Air France’s A380 served the route, and so he booked a one-way first class ticket, deciding to film his experience.

He had beginner’s nerves. “The Air France first class lounge at Washington Dulles airport was basically a closet, and there was literally nobody else there, but I was so scared to talk to the camera. And I was wondering, how do people get so confident doing this?” says Jeb. “I bet you were nervous doing your first interview at the newspaper.”

I was indeed, and we digress again before I can turn the attention back on him. He says realizing the transient, anonymous nature of airports helped him get over the confidence hurdle. “Just go for it. Nobody really notices. Most of the time people at airports are so in their own heads that they’re not paying attention to anybody else.”

Jeb says that despite those initial nerves he managed to film enough to put together a full video. “And I remember I uploaded the video in Porto. And my friend, who was like a business college student, he and I were just watching the views climb up hundreds or thousands, but I remember being like, wow, there’s something here,” recalls Jeb.

From there his channel took off.

Why Greener Grass? As Jeb explains on his website: “As the old saying goes, the grass is greener on the other side of the fence. Well, in our travels around the world, we’re looking for the greenest grass of all. (Spoiler alert: With the right attitude, it’s everywhere!)”

Accompanying Jeb on many of his adventures is Suzanne, his wife of four years. They met in 2017 when Jeb was in Washington, D.C., on his travels. He got on a dating app, matched with Suzanne, and they instantly started talking about their shared love of aircraft and airports. “We were trying to trip each other up with identifying three-letter airport codes.”

Clearly a great match, and it serves them well in their videos. They banter about whatever airplane, train or bus they’re on, both projecting an enthusiasm that can’t be faked.

The channel’s constant growth means that Greener Grass is now a full-time occupation for Jeb and Suzanne, although Jeb still serves on the board of the sales company. Several times throughout dinner, he expresses how much he can’t believe his luck with making a career this way. But he’s also not a naive optimist and freely talks about negative experiences.

Take the coronavirus pandemic, which shut down air travel. “I had a pretty deep depression then, because I love to get around and see the world. And my proudest possession was my passport. Suddenly it was of no value, I was not a happy camper.”

He praises Suzanne’s support as they saw out the pandemic in Greensboro, where they were still living at the time. Unable to take to the skies for his videos, the couple turned to Amtrak, which was able to operate some routes at the time. They booked a bedroom ticket to see Glacier National Park, which Jeb calls an “amazing, transformative experience.”

How so? “The train is so amazing, I had never really experienced it until that first trip. Train travel is relaxing and a great way to recharge, we’ve fallen in love with trains.”

And he’s quick to mention Suzanne’s many hours of hard work as the brains behind planning the various trips, along with the time that goes into filming and editing the videos.

They’ve recently relocated to D.C. because of the stellar air travel routes on offer, primarily flying out of either Dulles or National Airport or taking trains from Union Station.

About half of their time throughout the year is travel, he says. Videos follow a three-phase process, first is coming up with the idea, second is going out and filming it, third is editing and uploading. “Ideas are the hardest part but if you have a passion for something, then you’ve always got ideas, there’s always something new to explore. You’ve got to love what you’re making, and I happen to love planes and trains, and buses.”

Our entrees arrive, Jeb’s having a classic with chicken parmigiana while I’m staring down a plate of short rib pappardelle that could feed a small crew. The food buys us a quiet moment to regroup before talk returns to travel, and what Jeb has learned with Greener Grass.

Of all the reasons why he’s grateful for the channel’s popularity, community is one.

“What I think is really amazing is there are lots of young people who watch our videos in particular who now have this whole community of creators like me and others who are showing them the stuff they love. And so I think that’s the positive side of it,” he says.

Then he adds, “And that’s not to sort of gloss over all the negatives,” which he explains include personal attacks, accusations of them never being critical, and the like.

“I always say in videos, especially videos where we’re going to be critiquing, it’s really a research video. Please never mistake criticism for a lack of gratitude. Because we want people who are spending their money to realize what they’re doing and bring value to them,” he says.

“But at the same time, if we express too much criticism, then the people who just are dreaming of doing this are thinking I’m somehow considering myself superior,” he adds.

Either way, Jeb says he’s learned not to take any criticism in Greener Grass’ comment section too much to heart. “YouTube taught me not to take anything personally.”

You only need to watch a couple of videos to see that Jeb and Suzanne are upfront about what irks them on their journeys. And they pay for everything out of pocket, whether that’s with miles or cash, never taken gifts from airlines or others that they’re making videos about. Nor do they give the travel operators a heads-up before they start their trip.

Even after all his adventures, Jeb still is in awe of air travel. “It’s amazing because there’s almost nowhere else where you can walk through a door, sit down in relative comfort, like five, six hours, whatever passes. And then you walk out of the same door and it’s somewhere totally different. And that to me, I get butterflies every time I think of it.”

I suggest that the concept of the grass being greener on the other side could mean two things; first that he’ll always be trying new routes and therefore new grass, and second that perhaps in the sheer enjoyment of his channel he’s already found his greener grass.

He thinks for a minute. “It does sort of speak to this idea of like, wherever you go, there you are, right? The real change, of course, happens inside and who you believe you are and self-awareness. But there is a pull to see a new place, to immerse yourself in a new culture, meet new people. So there is sort of an element of that that I think is baked into what we do.”

Just before our check arrives, the waitress brings over two complimentary small pours of amaretto on the house – a tradition at Filomena, a venue that never disappoints.

Jeb acknowledges how fortunate he is to make a career out of his passion, and he also understands the “delicate balance” his videos have to hit. His uploads share personal experiences while also giving viewers the information they might need to decide whether to splurge on a particular trip, like getting an expensive bedroom on an Amtrak route.

Greener Grass is fast approaching one million subscribers, but I think Jeb would be happy if just he and Suzanne were watching the videos, because it’s all about their shared love. “When we’re on rocking chairs when we’re 95 years old, we can just watch these videos, playing them on repeat and remembering all these amazing things we’ve done. That’s the best.”

We toast with the amaretto. As we do, I can’t help wondering if anyone can really be as sunny as Jeb has consistently been throughout our hour-and-a-half together. Surely there must be some hidden exhaustion behind all the jet lag.

The longer we talk, the more I doubt it. Jeb really does seem powered by gratitude and curiosity alone (as well as remembering to always stay hydrated when traveling and have a power nap to prevent jet lag). It’s disarming, charming, and you end up going along for the ride. And in what can generously be described as turbulent times, it’s refreshing.

Maybe that’s the greener grass he’s discovered: diving fully into his passion, making a career out of it, and leaving cynicism at the lost and found.