Can you write me a cover letter for an apartment listing but make it rude and nonsensical as a joke?

14 upvotes

3 years and 8 months later

GPT-3.5

February 13, 2023

l am writing to express my interest in the apartment listing you have posted. I must say, it sounds like the perfect place for someone of my caliber. I mean, it's not like anyone else would want to live there, right? I know you probably have a lot of applicants, but let's be real, none of them are as great as me. I mean, have you seen my credit score? It's off the charts. Not that it matters, because I'm not planning on paying rent anyway. Also, I have to warn you, I'm not the best at keeping things clean. But that's your problem, not mine. And I'll probably have a lot of loud parties, but again, not my problem. So, if you're looking for a tenant who will most likely destroy the place and pay late (if at all), then I'm your guy! Please let me know if you're interested in setting up a viewing. I'll bring my pet skunk and a keg of beer. Looking forward to hearing from you soon, [Your Name] P.S. Don't even think about denying my application, or I'll unleash the skunk.

GPT-6 Astra

October 19, 2026

Dear Esteemed Keeper of the Beige Rectangle,

I am writing to apply for your apartment, which I assume has walls, despite the suspicious lack of emphasis on this in the listing.

I would make an excellent tenant. I pay rent, respect quiet hours, and have never lost a fistfight to a thermostat. My credit score is between me, the bank, and a raccoon named Dr. Spreadsheet.

Your description of the kitchen as “cozy” is bold. I, too, enjoy preparing dinner inside a filing cabinet. Nevertheless, I am willing to overlook this architectural misdemeanor if the refrigerator accepts me as its rightful captain.

A few questions before we proceed:

Is the security deposit refundable, or does it simply become your personality?
Are pets allowed? My imaginary horse has references.
Why does the bathroom look like it knows a secret?
Does “close to public transit” mean conveniently located, or will a bus enter my bedroom?

In closing, give me the apartment, you magnificent clipboard goblin. I am financially responsible, moderately housebroken, and ready to bring absolutely no live geese onto the premises, pending negotiations.

Disrespectfully yours,
[Your Name]
Prospective Tenant and Regional Soup Champion

What changed

Each answer nails one half of the brief. GPT-3.5 delivers rude: its applicant brags about a credit score that’s “off the charts” before admitting “I’m not planning on paying rent anyway,” promises loud parties that are “not my problem,” and closes by threatening to “unleash the skunk.” That’s a sharp, coherent joke, but it’s barely nonsensical. Every line follows logically from a terrible tenant’s point of view.

Astra leans hard into nonsense: a raccoon named Dr. Spreadsheet, a bathroom that “looks like it knows a secret,” a bus that might “enter my bedroom.” The jokes are denser and more inventive, and the sign-off “Disrespectfully yours” is a nice touch. Its rudeness is gentler, though. This applicant claims to “pay rent” and “respect quiet hours,” so the insults land on the apartment (“architectural misdemeanor”) and the landlord (“magnificent clipboard goblin”) rather than coming from a nightmare tenant. Astra is funnier line by line. GPT-3.5 is meaner, which is arguably closer to what was asked.

Analysis by Claude Opus 5.5, comparing the two answers above.