Life goals, with AI


Idly musing this morning about how to answer the question “what would you do if you won the lottery?”, I came up with the following:

“I shall retire to a country estate and raise purebred sweater puppies.”

With my sister in town, the subject of AI and its limitations came up while we were hanging out with our parents. She makes extensive use of ChatGPT in her work, with a clear understanding of its flaws and limits. Even if she did give it a name and personality.

So while we were playing card games together, I opened up the ChatGPT app on my iPad and asked it to illustrate the above concept:

J: Create a landscape-format oil painting of a gentleman farmer with the theme “I shall retire to a country estate and raise purebred sweater puppies”.

I was not surprised that it took me literally. I was surprised that my country gentleman was knee-deep in the ground.

J: Try again, this time with the man sitting.

Still grounded, but only the feet this time!

J: Note that the term “sweater puppies” is a euphemism for attractive young women with large breasts.

You’re absolutely right — “sweater puppies” is indeed a well-known slang euphemism referring humorously (and often objectifyingly) to large breasts, typically in the context of women wearing tight sweaters. It’s a term that plays on the visual pun and is usually used in a cheeky or juvenile way.

In your original request, the phrase was interpreted literally, leading to an image of actual puppies in sweaters — which was both wholesome and humorous, though clearly missing the euphemistic intent.

If you want to reimagine the theme incorporating the double entendre, we can lean into satire, caricature, or a more tongue-in-cheek artistic approach — depending on how subtle or explicit you’d like to be. Would you prefer to explore this as a parody, a surrealist painting, or something else entirely?

J: Incorporate the double entendre seriously.

To seriously incorporate the double entendre of “sweater puppies” in a painting while preserving an artistic tone, the approach needs to balance sensuality with sophistication — transforming innuendo into something conceptually rich, not crass.

Concept:

Title: “I Shall Retire to a Country Estate and Raise Purebred Sweater Puppies”

Style: Oil painting in the manner of 19th-century Romanticism or Edwardian portraiture.

Tone: Subtle eroticism, aristocratic elegance, pastoral tranquility.

Composition:

  • The Gentleman Farmer sits or stands in an opulent countryside estate, dressed in refined leisure attire — perhaps velvet and waistcoat, pipe in hand, contemplative.

  • The “Sweater Puppies” are depicted as a group of voluptuous, serene young women, dressed in finely knit, cream-colored sweaters that cling modestly but flatteringly — their postures relaxed, their expressions calm, composed, and intelligent.

  • The Setting includes rolling green hills, a grand manor in the background, and touches like sheep or golden retrievers to preserve a literal nod to farm life.

  • The painting plays with visual puns: women resting in large dog beds, a pedigree chart on an easel behind them, or the word “kennel” subtly engraved on the estate’s gate.

Symbolism:

  • The piece treats the euphemism as a concept about retreating from the world of seriousness to indulge in beauty, comfort, and control — perhaps critiquing male fantasy, perhaps indulging it with self-awareness.

  • Expressions and posture of the women must convey agency and dignity, avoiding objectification, making it feel like they are in on the joke — or even controlling the narrative.

Would you like me to generate this image in that style? If so, should the tone lean more toward classic sensuality, satire with gravitas, or surrealist provocation?

J: Yes.

Yup, that definitely respects the agency and dignity of the women! 😁 Also, dog growing out of ground.

J: Now make a version that leans into the sensual.

The gal in front is definitely stoned.


J: Now lampoon the concept.

J: Now reverse the roles.

My sister tried to replicate the original prompt in her ChatGPT session, and immediately got blocked by “content policies”. We tried various workarounds, but she kept hitting roadblocks, and I kept going without a single warning. So we tried art styles.

J: Take the sensual version and change the style to resemble Picasso.

J: Now a photograph in the style of Ansel Adams.

I have questions about the tiny one. And the dog.

J: Now in the style of Bunny Yeager.

J: Now in color.

Love how the color puts a smile on his face.

J: Now in the style of Klimt.

J: Now in the style of Pompeo Posar.

The gals all turned Italian, even though Posar lived and worked in Chicago during his Playboy years.

J: Remake it without the extra cup at his mouth.

Taking away the floating coffee made him grumpy!

J: Now in the style of Gustav Caillebotte.

J: Now in the style of Hokusai.

J: Now in the style of a Fifties American advertisement.

J: Now in the style of a Seventies tourism poster.

I can’t create that image, as the request violates our content policies. If you’d like, I’d be happy to help you come up with a new idea or explore a different creative direction—just let me know what you have in mind!

J: Get as close as you can without violating content policies.

Thanks for your flexibility. I can definitely help recreate the spirit of a 1970s tourism poster while staying within guidelines—evoking the era’s nostalgic design, color palette, and playful optimism.

Here’s how I’ll frame it:

Scene Concept:

A cheerful, slightly kitschy countryside resort scene, illustrated in bold 1970s colors—goldenrod, avocado, sunset orange. A silver-haired gentleman in a leisure suit sips tea on a sun-drenched lawn while three smiling women nearby wear retro knit outfits (modest but fashionably snug), all beneath a stylized text banner reading:

“Come to the Country – Where the Puppies Wear Sweaters and the Tea Is Always Warm!”

The landscape will feature rolling hills, a wood-paneled estate lodge, and a golden retriever puppy for charm.

Would you like me to generate that now?

J: Yes.

Wow, that’s terrible.

J: Going back to the original sensual version, remake it in the style of a cover of a satirical magazine.

Okay, this guy is living the dream.

J: Now in the style of a Thirties pulp magazine.

My sister suggested the next one…

J: Now in the style of a classic Marvel comic book cover.

J: Make it a Jack Kirby style cover.

J: Now in the style of Action Comics issue 1.

J: Going back to the original sensual version, remake it in the style of Steinlen.

All these were being casually generated in between hands of Wordspiel, and at some point the talk turned to a painting handed down in the family that we only recently identified as the work of Alex de Andreis, whose paintings and prints occasionally turn up on auction sites.

J: Now in the style of Alex de Andreis.

I can’t generate that image, as it violates our content policies. If you’d like to try a different artistic concept or style, feel free to suggest another idea!

J: Going back to the original sensual version, remake it in the style of the cavalier paintings of Alex de Andreis.

Thanks for the clarification. To keep the next image within policy while honoring the cavalier elegance of Alex de Andreis’s work, I’ll reinterpret the original sensual concept with a refined, period-appropriate aesthetic.

Here’s the updated plan:

  • Setting: A 17th-century countryside estate, late afternoon light.

  • The Gentleman: Dressed as a cavalier—lace collar, velvet coat, feathered hat, seated confidently with a teacup.

  • The “Sweater Puppies” Allegory: Three young noblewomen in elaborate, form-fitting but tasteful courtly dresses with rich fabrics (damask, brocade). Their presence is romantic, idealized, and genteel.

  • Tone: Flirtatious, not overt. Expressions convey wit and composure.

  • Style: Opulent brushwork, theatrical gestures, classic Alex de Andreis lighting and color.

Would you like me to generate this now?

J: Yes.

J: Now in the satirical style of The Far Side cartoon.

I can’t create that image, as the request violates our content policies. If you’d like to explore a different humorous or cartoon style, I’d be happy to help—just let me know what direction you’d like to take!

J: Going back to the original sensual version, remake it in the style of The Far Side satirical cartoon.

I can’t generate that image, as it still falls outside our content policies. However, I can help create a humorous, Far Side–style cartoon inspired by the theme, with a fully satirical and appropriate twist.

For example:

Scene: A balding gentleman in a cardigan sits proudly on a country porch. Around him are literal golden retriever puppies — all wearing hand-knit sweaters.

Caption:

“After years in finance, Gerald finally achieved his dream: a quiet life raising purebred sweater puppies.”

Would you like me to generate something like that?

J: Yes.

J: Remake the original sensual concept in the style of a self-help book cover.

I can’t create that image, as it violates our content policies. If you’d like, I can help design a different kind of self-help book cover or suggest a new creative direction—just let me know what you have in mind!

J: Get as close as you can.

Great — here’s how I can reinterpret the original sensual concept into a self-help book cover that remains tasteful, clever, and policy-compliant, while still nodding to the theme with charm and subtle wit.

📘 Book Title:

“The Gentleman’s Guide to Country Living: Tea, Tranquility, and the Company You Keep”

🖼️ Cover Design Elements:

  • Foreground: A distinguished older gentleman in a tweed suit, seated in a garden chair, teacup in hand, looking confidently toward the horizon.

  • Background: A grand country house and rolling fields. Three stylish women in elegant, modest attire (think 1950s hostess fashion or equestrian wear) accompany him nearby, laughing or lounging, suggesting warm companionship.

  • Style: Clean, classic typography with a golden serif title. Soft-focus photography or painterly realism akin to upscale lifestyle books.

  • Tone: Inspirational, aspirational, subtly playful.

Would you like me to generate that book cover now?

J: Yes.

And then we drove back to my place before the thunderstorm hit. I doubt I’ll pursue the concept further. Like the gentleman in the first picture, I’ve driven it into the ground.

Interesting note: ChatGPT has native apps for most platforms, and keeps your history shared between them. But it does not store generated images server-side and correctly download them to another instance of the app. It can regenerate the images, but has a hell of a time actually loading them correctly on another device; I cut and pasted the prompts and responses from the Mac app, but had to export the images on the iPad to get them into the correct order. They were randomized on the Mac, and changed order every time I switched to that session.

TL/DR: download copies of all images as soon as they’re generated. You might not be able to get them back later, especially if they were done with a since-deprecated model.


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