‘I’m obviously a radical centrist’: Cities by Diana says how she really feels

Diana Regan has a perfect social media strategy: Choose one city that’s in the Bay Area and one that’s not. Assert that the Bay Area city (Fairfield, perhaps) is not actually in the Bay, and the other city (let’s say Davis) is. Watch the 😡 and 😂 reactions roll in.

This is just one of several provocative formulae that Regan, 38, has employed online, where she has amassed more than half a million followers under her persona Cities by Diana. Her hyperspecific videos about highway infrastructure, car-centric city planning, and archetypes of the Western U.S. have won fans ranging from democratic socialist state legislator Alex Lee to right-wing streamer Asmongold.

She’s not an urbanist by trade. Regan, originally from Fresno, moved to the Bay Area in 2013 and worked the rat race, cycling through retail, receptionist, and sales jobs for a decade. During the pandemic, she was locked up indoors playing the video game “Cities: Skylines,” in which players create, manage, and drive through cities. Soon, she was using footage of herself playing to make YouTube satires and commentary (opens in new tab), which spun off into her popular Instagram (opens in new tab) and TikTok (opens in new tab) accounts. When she was laid off in 2023, she was making enough money from these social platforms to support herself. The rest is history.

We spoke with Regan about memes, radical centrism, and, alas, the Great Highway. 

This conversation has been condensed and edited for clarity.

I want to give you a list of places, and you tell me if they‘re in the Bay Area. 

OK.

Tracy. 

No. 

Livermore.

Technically yes.

American Canyon.

Technically yes. 

Gilroy. 

Technically yes, but hell no. 

Fresno.

No. 

Palm Springs.

No. 

Salt Lake City. 

Yes. 

And, of course, the Tuscan countryside (opens in new tab). 

Oh, absolutely.

Did growing up in Fresno inform your urbanism?

I have no urbanism. I mean, I do, but I don’t really. What got me thinking about it was that during the pandemic, I spent a lot of time in San Jose. I had been living in the East Bay for 10 years at this point, and I was car-free for five. And then I was visiting a lot of people in the South Bay and dating somebody there, and I was just like, damn, you have to drive everywhere. That brought me back to where I grew up, which was the same thing but worse. 

You were also an early member of the popular Facebook group New Urbanist Memes for Transit-Oriented Teens (opens in new tab).

I was in that group when there were like 2,000 members, but I got banned from it for making a joke about a Republican politician being closeted. I literally joined it because it said “memes.” I mean, I’ve always kind of known about this stuff. I ride my bike everywhere. But I didn’t think about it on the level that a lot of people in that group do. 

Your posts have a mix of leftism and urbanism that seems to resonate. But why do so many Bay Area urbanists love market solutions?

I don’t know. I think that the whole YIMBY thing is really popular here because it’s in opposition to NIMBYs. I do agree with them — obviously, we need to make it easier to increase the housing supply. But what do you do with the people that are already there once commercial landlords are like, “I can renovate my building and charge more rent”? 

In Downtown Oakland, the new housing did help. Rent stabilized for a while. But at the same time, commercial speculators pushed out the legacy businesses, because they saw dollar signs. 

There are lefty urbanists, though. [Assemblymember] Alex Lee has followed me for longer than almost anyone. He’s on my Close Friends stories on IG.

What’s your favorite passage from Robert Caro’s “The Power Broker”?

It’s the one where Robert Moses emerges out of the East River, and he’s 50 feet tall, and he screams at the city: “Just one more lane, bro.”

Would you ever want to be a city planner?

I don’t know. I’m pretty happy with what I do now. Planning is not necessarily my passion. I have so much other shit that I care about too. People just focus on the planning shit because it gets views.

Have you gotten into any crazy beefs or fielded threats from strangers online?

Oh, all the time. I remember the first time it really happened was when I made a video saying that Amsterdam needed more freeways. I had all these Dutch people sending me death threats. “Why would you say that? Why would you do that?” And I thought, oh, maybe they didn’t catch the humor because of cultural differences. But then Americans were doing it too. 

But some people who thought it wasn’t satire were like, “Hell yeah. This, but unironically.”Everybody projects their own ideas onto me, whether they are on the left or the right.

How would you describe yourself politically?

Obviously, I am a radical centrist. I only believe in centrism. No, I’m just kidding. I generally lean to the left, but I have some unorthodox opinions. I support the Second Amendment. With regard to planning, I’m just like, housing is not going to save you. More housing is not going to fix you. 

High-speed rail, too. I was visiting family in Fresno, and I was driving through where they were building the high-speed rail, and it divided a lot of the poor neighborhoods. I made this little video like, highways divide cities — we should build high-speed rail! And then I showed all the high-speed rail under construction. These projects do the same thing and are planned with the same hostility as highways. Look at the West Oakland BART station. Why the fuck did they make that above ground? What was happening on Seventh Street before the BART was built? They had all the jazz clubs and all the blues clubs and all the Black people that lived there. 

A lot of people don’t understand that, or they’re like, “No, but transit is good.” And it’s like, sure, but how do you build it to ensure it’s not going to do the same exact thing that highways did?

The power woker. 

Yeah.

You get so specific with your regional profiles. Do you have on-the-ground consultants?

Sometimes yes, sometimes no. I did a video about Cedar Rapids, Iowa, and I have a friend who’s from that area who gave me a lot of help. Sometimes I will ask followers on my story: Does anybody know about this place? But a lot of times I’ll just do the research. And some of it is just based on my real-life experience, like when I drove three hours in Montana to buy a Labubu. I’ve been to 32 states or something, so a lot of it is just based on having gone through a place.

Can we get an earnest Great Highway take?

[Sunset Dunes] is nice, but I understand why some residents are pissed. It has made traffic worse, and they did nothing to offer up any alternatives. But on the other hand, the road was going to go away anyway — they had to take it out because of erosion. So it’s like, what do you do? I don’t have the answer for that. I made a video (opens in new tab) about it and tried to interview people who were not in support of the park, and I couldn’t find anybody when I was there. People got really mad at me for that. 

The big problem is that they gave nobody any alternatives. Like, hey, let’s make it easier for you to take a bus. Let’s build a Muni train line that goes north-south. They won’t do that. 

People misunderstand what you do and want to project their own views and ideologies onto it. Does that bother you?

A lot of men don’t listen to me because they hear my voice and they think, “Oh, you’re annoying.” Some people who misunderstand me are kids. And then a lot of people who like me are projecting what they want onto me because they have developed a parasocial relationship. They think all my takes are based and awesome, and then they get really upset when I say something they disagree with.

I am spending time editing video because I love to edit video. I love to write voiceover scripts, I love to find music, I love to compile it all into a piece. Essentially, that is my job, but it is also performance art. 

If people project something really nasty onto me, and say I believe something I don’t, I’m gonna say something. But if they want to believe whatever they want to believe, let them. I can’t control how people interpret my content. Once you create a piece of art, so to speak, it’s not for you anymore. People love that Radiohead song “Creep.” But the guy that wrote it hates that song. He wrote it because he felt like a creep because he liked this girl that didn’t like him. And now he has to relive this weird feeling every time he has to sing it. Other people, they just love it.