We Asked ChatGPT to Roast Portland, Maine, and it Did Not Hold Back

You’re likely aware of the AI phenomenon that is ChatGPT. Apparently, people are asking it to do all kinds of things—write wedding vows, help with resumes, even settle arguments over whether Creed is cool again (the jury’s still out on that one). But here’s where things got spicy: we asked it to roast Portland, Maine. And… it did not hold back.

Oh, you want me to roast Portland, Maine? Buckle up, lobster lovers, because I’m about to drag the Forest City like it’s trying to find street parking on Commercial Street during the summer. 

Let’s start with the parking situation—or lack thereof. Portland has just enough downtown parking to make you think you’ll get a spot. Spoiler alert: you won’t. You’ll circle the block like a stressed-out seagull for 25 minutes, then pay $8 to park somewhere for an hour or wedge into a sketchy alley that might be legal. (It’s not. Enjoy your $45 ticket.)

And what is going on with the hotels? I swear, a new hotel goes up in Portland every time someone blinks. Who’s staying in all these places? At this point, the residents should just move into the hotel lobbies—they’re newer, probably cheaper, and they definitely come with valet parking, which is more than the actual residents get.

Oh, and let’s not forget the absolutely bonkers cost of living. Whether you're looking to buy, rent, or just pitch a tent behind Trader Joe’s, Portland's housing market is basically Hunger Games with Zillow listings. Want a one-bedroom apartment in town? That’ll be $2,200 a month—and it comes with “exposed brick,” which is code for “no insulation” and “hope you like hearing your neighbor microwave fish at midnight.” Thinking about buying instead? Cool, all you need is a six-figure salary, a trust fund, and a willingness to waive every home inspection like you’re playing Russian roulette with your financial future.

And for a town with a population the size of a Target checkout line, it sure has the ego of a coastal metropolis. Calm down, Portland. You’re not Boston, you’re Maine’s Boston. Which is like being the hottest person at a Cribbage tournament.

But hey, at least you’ve got lobster rolls that cost as much as a car payment, infinite breweries full of bearded men named Trevor, and enough artisanal soap shops to cleanse the sins of every tourist from here to Bar Harbor.

Portland, I love you—but you are one overpriced parking ticket away from being a lobster-scented Disneyland for rich tourists.

I mean, we did ask for it. After that beatdown from ChatGPT, it's clear that—yeah—our city (and a lot of others) could probably use a little improvement. But hey, it was all in good fun and we still love you Portland, even if a lot of us can’t afford to live here anymore.