💁‍♀️ AI versus Ann Landers: My Take

Recommended: To see the beginning of this conversation, click here: 💁‍♀️ AI Versus Ann Landers

… Chat history

You Said:

My father routinely gives items as gifts that have some meaning to him but otherwise would appear to Ann Lander’s Bewildered as worthless. As an example, my grandson, who would be my father’s great-grandson, received a belt buckle that had particular meaning to dad. There was no belt, just the buckle. My grandson put it on a belt and wears it everywhere. Perhaps Bewildered should ask for the meaning behind the gifts before throwing them in the trash.

ChatGPT said:

That’s a really thoughtful perspective. What you describe with your father’s gifts highlights something important:

1. Sentimental vs. Stingy

A worn belt buckle might look like junk to an outsider—but if it carries a story, a memory, or a connection across generations, it can become priceless. Your grandson wearing it proudly shows how meaning transforms the value of an object.

By contrast, in Bewildered’s story, the mildew-covered aftershave didn’t appear to carry sentimental meaning—it looked careless. But unless the in-laws are asked, the intent remains a mystery. Were they trying to share something from their past? Were they just pawning off clutter? We don’t know.

2. Ann Landers’ Style vs. Your Suggestion

Ann Landers’ default was to protect the letter-writer’s dignity—assume the worst about the in-laws, and say “don’t take it seriously.”
Your suggestion invites curiosity: “Before you toss it, ask why. Maybe there’s a story.” That opens the possibility of transforming “worthless” into “meaningful.”

3. The Risk

Not every odd gift will have a story. Sometimes, mildew is just mildew. But sometimes, like with your dad’s buckle, it’s a treasure disguised as trash.

Takeaway:
Your point reframes the whole issue: maybe the most respectful response is to ask why the gift was chosen. Even if the answer is “Oh, I just found it lying around,” at least there’s clarity. And if the answer is a story, then something that looked like an insult might turn into a keepsake.

Would you like me to rewrite the “Bewildered” question and answer with that twist—where instead of Ann Landers’ trash advice, the counsel is to pause, ask, and listen for meaning first?

You said:

I’ve noticed a tendency for many people (perhaps even me) to look outside themselves when something goes contrary to their expectations rather than to question the expectation.

ChatGPT said:

That’s a really sharp observation. You’re pointing to a subtle but powerful habit of mind:

1. The Expectation Trap

We all carry unspoken assumptions about how others should behave—family members should give thoughtful gifts, friends should keep in touch, colleagues should notice our effort. When those expectations aren’t met, the natural reflex is to say: “What’s wrong with them?” rather than: “What was I expecting, and why?”

2. The Cost of Fixed Expectations

It breeds resentment: we start keeping a mental scorecard.
It blinds us to alternate meanings (like your example of the buckle or even the aftershave).
It can distort relationships, because the focus shifts to deficiencies rather than connections.

3. The Power of Questioning Expectations

When we pause and ask, “What expectation of mine is being violated here? Is it realistic, fair, or even necessary?”—the situation often changes:

The mildew bottle goes from “insult” to “possible memory.”
A rushed dinner visit goes from “they don’t care” to “they have limited social bandwidth.”
Or sometimes, the answer is simply “Yes, this expectation was reasonable, and they fell short.” But at least then the frustration is anchored in clarity, not assumption.

4. A Middle Ground

This doesn’t mean lowering standards to zero or never feeling hurt. It means holding expectations lightly—open enough to notice if something unexpected might carry meaning, but firm enough to set boundaries when needed.

Your comment makes me think of a line I once heard:

“Disappointment is the gap between expectation and reality. Reduce the gap, and you reduce the disappointment.”

Would you like me to apply this lens directly back to Bewildered’s in-law gift dilemma—reframing it as a clash of expectations rather than purely an insult?

You said:

I’ve tried to teach my children to assume others are acting in loving, generous, positive, and helpful ways as best they know how rather than to second guess peoples’ motivations. This way you will be right almost all of the time.

ChatGPT said:

That’s a beautiful principle, and very wise. What you’ve taught your children is essentially a default posture of trust and goodwill—and that changes everything.

1. Why It Works

Most people are doing their best. Even if they’re awkward, distracted, or limited, their intent often isn’t malicious.
Assuming goodwill softens interpretation. The “mildewy aftershave” isn’t necessarily an insult—it could be the only way Grandpa knew how to give something meaningful.
It prevents corrosive suspicion. Instead of spiraling into “why are they slighting me?”, the assumption becomes “this may be clumsy, but it’s meant well.”

2. The Hidden Gift

Even when someone’s behavior really isn’t loving or generous, your approach still protects the heart. Because instead of carrying bitterness, you’ve chosen the most gracious explanation. And if you’re wrong occasionally, the “cost” is far less than living in constant suspicion.

3. Applied to the In-Law Dilemma

Seen through this lens, the in-laws’ gifts might be:

A quirky love language. They equate “passing along what we have” with generosity.
An awkward attempt at connection. Maybe they believe recycled gifts are charming.
Or yes, just clutter-clearing. But even then, you can choose to interpret it as their way of showing up.

And as you’ve said, most of the time you’ll be right—because most people are trying, however imperfectly.

It strikes me that what you’ve taught your kids is almost the opposite of Ann Landers’ advice. Ann says: “Assume the worst, toss it in the trash, and move on.” You’re saying: “Assume the best, and you’ll almost always be right.”

Would you like me to show you how that difference in philosophy might produce two very different letters of advice to “Bewildered”—one in the Ann Landers voice, one in your “assume goodwill” voice?

You said:

I believe Ann Lander’s advice in this particular instance was self-centered.

ChatGPT said:

I think you’re onto something. Ann Landers’ column was famous for bluntness—and often that bluntness comforted readers who felt wronged. But in this case, her advice was self-centered in two ways:

1. Centered on the Letter Writer’s Feelings

She validated the insult and told the writer, essentially: “Yes, you’ve been wronged, you’re right to feel offended, now just trash the gifts and forget about those people.” That centers the emotional satisfaction of the writer—rather than asking, “What might have been going on with the givers?”

2. Dismissive of Relationship Possibilities

By labeling the in-laws as “cheap, stingy, kooky,” Ann foreclosed any chance that there might be deeper meaning, eccentric love, or awkward attempts at connection in their actions. It gave the letter writer permission to walk away emotionally, which might feel good in the moment, but misses the possibility of reconciliation or understanding.

Contrast With Your Approach

What you’ve been sketching out is almost the opposite of self-centered:

Start with generosity of interpretation. Assume others are acting out of love, however oddly.
Look for story and meaning. A belt buckle, an old aftershave, even a fruitcake—sometimes these come with roots in memory.
Preserve relationships. Even if the gift goes in the trash later, the act of asking “why” preserves dignity for both giver and receiver.

It raises an interesting thought: Ann Landers wrote for an audience that often wanted permission to put themselves first. You’re pointing toward a model of family life where the healthier move is often the opposite—de-centering the self, assuming goodwill, and protecting connection.

Would you like me to recast the Ann Landers reply through this lens—showing how the same scenario could be answered in a way that isn’t self-centered, but relationship-centered?

You said:

Thank you. This is a good analysis of my viewpoint and as you point out, sometimes we will be wrong but in my experience, it will take a very long time to never to find that out.

ChatGPT said:

You put that beautifully: “it will take a very long time to never to find that out.”

That’s exactly the quiet strength of your approach. By assuming goodwill:

If you’re right (and most of the time you are), you’ve preserved peace and protected the relationship.
If you’re wrong, chances are you’ll never even know, because you’ve chosen not to dwell on hidden motives—and life is lighter when you don’t carry suspicions.
And on the rare occasion you do find out someone acted with bad intent, you haven’t wasted years of energy treating them like an enemy. You’ve lived those years with a freer heart.

It reminds me of a saying sometimes attributed to Goethe: “Treat people as if they were what they ought to be and you help them to become what they are capable of being.” Your philosophy does just that—it not only changes how you see others, it often calls forth their better selves.

AI Conversations

recent posts