
Chat GPT Roasts Wallingford and it’s Not That Bad
I was scrolling through my TikTok feed the other day when I stumbled upon a video that hit a few of my sweet spots — it had a Connecticut theme and then came the word roast.

The video was posted by a u/wesleykrombelrealtor who wrote:
"I asked ChatGPT to roast Wallingford, CT. Here is the Result"
@wesleykrombelrealtor I love my hometown, but this is funny #Roast #ChatGPT #Wallingford #Connecticut ♬ original sound - WesleyKrombelRealtor
Not bad for a robot.
Joke rundown:
"Welcome to Wallingford, the senior citizen capital of Connecticut, where the median age is 'get off my lawn.'"
"The Dunkin' District, with more Dunkin' Donuts than common sense. Caffeine is the only thing keeping this town awake."
"Consider riding the train via the town's state-of-the-art, multi-million-dollar train station that no one uses."
"The Bermuda Triangle of Highways, where Route 5, I-91, and the Merritt Parkway form a cursed vortex where drivers forget basic traffic laws."
"Wallingford Weather Roulette: it's either 95°F and humid, or bitterly cold and dark."
"Looking for a good dive bar? Try Lenny's Cafe or Grand Central Cafe — sure to impress."
"Wallingford has one of the highest number of liquor stores per capita in America."
"Wallingford Facebook groups are a circus: one part town news, two parts people arguing about leaf pickup like it's life or death."
"Choate is a prep school in town. It's like having a millionaire relative who lives in your basement but pretends they don't know you."
"Route 5, the highway of car dealerships. Car broke down. No worries. Just walk 10 feet from your vehicle and you'll be touching a car for sale."
First off, dive bars are amazing so I'm not laughing at that. Instead, I'm writing the names of those bars down, so I know where to go the next time I pass through Wallingford.
That last joke about Route 5 being the highway of car dealerships had great potential but fell flat at end. It got too wordy with "touching a car for sale." it just needs to end more like this, "just walk 10 feet from your vehicle and grab a new one." The idea being that there is such an overwhelming number of vehicles for sale that you can just get in one and drive off. It's almost like no one would notice. AI is better at crafting jokes than I thought it would be but it still needs an assist from humans to punch it up.
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