We asked ChatGPT to roast Winston-Salem

And the AI chatbot didn’t hold back on the Twin city.

WStoday: Winston-Salem skyline

Like Charlie Chaplin once said, “A day without laughter is a day wasted.”

Photo by @tim_hutch

We set our sidesplitting sights on a good old-fashioned, lighthearted comedy roast of Winston-Salem and took our humorous intent to ChatGPT, the online AI chatbot that uses natural language processors to generate text-based responses.

Here’s what it had to say — if you can handle it.

Fun fact: Comedy roasts date back to 1949, when the former Friars Club in New York City roasted vaudeville actor and singer Maurice Chevalier.

Can you roast Winston-Salem, NC?
Winston-Salem: A city that feels like it was half-built, then paused for BBQ. It’s all coffee shops, tobacco nostalgia, and a food scene that’s all comfort, no thrill. If you’re into quiet, quirky vibes, it’s your spot — if you’re craving excitement, maybe drive through to somewhere else.

How’s the traffic?
Winston-Salem traffic is like a lazy river—nothing moves fast, but nothing really blocks you either. Rush hour’s just a couple of extra cars, and the worst bottleneck is probably when everyone’s trying to figure out how to merge at the one confusing intersection. It’s like a traffic yoga class.

OK, but our food scene isn’t all that bad.
Winston-Salem’s food scene is like a never-ending buffet of Southern comfort—heavy on fried chicken and mashed potatoes, light on variety. It’s the place where “fresh” means “from the freezer,” and your taste buds will be confused by how many different ways you can cook a biscuit.

Alright, alright. What’s the most overrated thing about Winston-Salem?
The most overrated part? Probably the “hip” downtown bar scene. You get overpacked spots with overpriced cocktails, people trying to be “seen,” and DJs playing the same top-40 hits from five years ago.

WStoday: Streets of Old Salem in Winston-Salem, North Carolina

At the end of the day, we love living here and wouldn’t change a thing that makes Winston-Salem special — even if ChatGPT thinks Old Salem is just ride-less historical themepark.

Photo by WStoday

Poke some fun at the weather here in Winston-Salem.
Winston-Salem’s weather is indecisive — sun one minute, rain the next, then back to humidity. You’ll need a T-shirt, hoodie, and umbrella just to leave the house. It’s like the weather’s playing hide and seek with your wardrobe.

What three words summarize your roast of Winston-Salem?
Slow, humid, quirky.

Give Winston-Salem a backhanded compliment.
Winston-Salem: It’s the perfect place if you’re into small-town charm… with just enough weirdness to keep you wondering if you’ve accidentally stepped into a time loop.

Give Winston-Salem a real compliment.
Winston-Salem has a unique charm with its blend of history and modern vibe — whether it’s the growing craft beer scene or the picturesque downtown, there’s a real sense of community and creativity. Plus, you can’t beat the Southern hospitality; it’s the kind of place where people still wave at strangers.

Editor’s note: The ChatGPT responses have been edited for brevity.

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