💁‍♀️ AI Versus Ann Landers

What happens when you ask ChatGPT for advice as opposed to asking the same question of Ann Landers? I explore this very idea as I examine the boundaries and nature of Artificial Intelligence in my conversation with AI below.

Chat history

You said:

Here’s a scenario (not me): I have always maintained it’s the thought that counts when it comes to gifts. In that light, I’d like to know what you think. Over the years, my husband, our children and I have received an odd selection of gifts from my in-laws. They are always used — from their attic, a thrift shop or a fire sale, or otherwise recycled. We have laughed it off, decided that they are eccentric and disposed of the gifts. I can understand used books, clothing, jewelry and toys, but last Christmas, they went a bit too far. Our teenage son received an assortment of used aftershave — complete with mildew on the bottles. He just laughed and tossed it in the trash. My husband and I, however, felt insulted. These people are financially well to-do. They see our children only when they visit on birthdays or Christmas. They stay through dinner and leave just before dessert is served. Then, we don’t hear from them until the next major event. When we ask them to spend more time with the grandchildren, they make all kinds of excuses for why they can’t manage it. After being rebuffed numerous times, our children have stopped asking about them. Ann, if it’s “the thought that counts,” what thought can there be behind such insulting gifts? I hesitate to ask them, because I do not want to hurt my husband, but I would appreciate your opinion.

ChatGPT said:

This is a tough one. On the surface, the gifts themselves seem less about generosity and more about getting through an obligation. Used aftershave with mildew is not “eccentric”—it’s careless, if not insulting.

But gifts are symbols, not just objects. When people who are financially comfortable repeatedly give secondhand, thoughtless items, it can signal a few possible “thoughts” behind them:

1. Obligation Over Relationship

They may feel that gift-giving is simply a box to check. Instead of using it as a way to connect, they grab whatever is at hand to fulfill the duty. The lack of effort can communicate distance rather than affection.

2. Avoidance of Closeness

Their pattern—brief visits, leaving before dessert, dodging time with the grandchildren—suggests that they may not want deep involvement. The gifts may reinforce this distance: impersonal, token gestures instead of meaningful connections.

3. Self-Centeredness or Eccentricity

Sometimes people project their own values—perhaps they think “used is quirky” or “waste not, want not.” They may genuinely believe they’re being resourceful, without realizing it’s hurtful.

4. Passive-Aggression

In less charitable terms, the gifts could carry an undercurrent of hostility or control—showing up, but not showing care. If they know how the gifts land and persist anyway, that suggests intentional disregard.

What You Can Do

Separate your husband’s feelings from your own. He may feel caught between loyalty to his parents and awareness of how their behavior hurts his family.
Don’t expect the gifts to change. It’s unlikely they suddenly become warm, thoughtful grandparents.
Focus on your own family’s traditions. Your children already seem to have figured out that the in-laws’ gifts don’t define their worth. Emphasizing love and meaningful exchanges at home can offset the sting.
Consider gentle honesty (if it feels safe). Something as simple as: “We appreciate the thought, but the children don’t really need more hand-me-downs. What they’d really enjoy is time with you.” Whether they accept or retreat further, you’ll at least have stated the truth kindly.

If, as you say, “it’s the thought that counts,” the thought here seems to be: “We are unwilling or unable to invest ourselves in you in a meaningful way.” Painful as that is, the clarity can help you decide how much emotional energy to spend hoping they’ll change.

Would you like me to suggest how you might phrase a direct but tactful conversation with them—one that protects your husband’s feelings but still sets boundaries?

You said:

Here’s Ann Lander’s response: Here are a few adjectives: cheap, no-class, stingy, tightwads, and toss in stupid, weird and kooky, since they apparently believe they are getting away with it. How sad that they’re missing out on their grandchildren’s lives. When their crummy gifts arrive, just toss them in the trashcan, and let it go at that. Would you believe a woman in Minnesota wrote to tell me that last Christmas she got the same fruitcake she had given the woman two years before? Any comments?

ChatGPT said:

Yes—that response is classic Ann Landers: blunt, cutting, and just a touch amused.

A few thoughts:

1. Tone

Ann doesn’t bother with nuance—she goes straight to calling out the behavior as “cheap” and “stingy,” and then escalates to “stupid, weird, and kooky.” That’s her way of giving the letter-writer permission to feel insulted rather than guilty about it. She validates the frustration by putting the blame squarely on the in-laws.

2. Practical Advice

Her advice—“toss them in the trashcan, and let it go at that”—is pragmatic. She’s not recommending confrontation, soul-searching, or diplomacy. Instead, she recognizes that the in-laws aren’t likely to change, so the healthiest move is to stop giving the gifts any power.

3. Perspective and Humor

She defuses some of the sting by adding humor—the anecdote about the recycled fruitcake. That’s both a wink to the reader (“you’re not alone, this is a common silliness”) and a way of saying, “don’t take these people too seriously.”

If I contrast it with the more nuanced approach I offered earlier:

Ann Landers’ style: Name the behavior for what it is, laugh at it, and refuse to let it matter.
My earlier style: Analyze the motives, consider the relationship dynamics, and offer ways to communicate or cope.

Both are valid, depending on what the letter-writer needs—quick validation and a laugh, or a thoughtful path forward.

Do you want me to rewrite your original scenario’s question-and-answer in Ann Landers’ biting style—so you can see how different it feels side by side?

You said:

Yes, that would be helpful.

ChatGPT said:

Great—here’s your original scenario re-cast in Ann Landers’ sharp, no-nonsense voice:

Dear Ann Landers,
Over the years, my in-laws have given our family an odd assortment of gifts. Every single one has been used—pulled out of their attic, snagged at a thrift shop, or dragged home from a fire sale. We’ve laughed it off, but last Christmas they went too far. Our teenage son got a bundle of used aftershave—bottles complete with mildew. He laughed and threw it out. My husband and I, however, felt insulted.

These people are well-to-do. They visit only on birthdays or Christmas, leave before dessert, and avoid spending time with the grandchildren. Our kids have stopped asking about them. If it’s “the thought that counts,” what thought is behind such gifts?

— Bewildered

Dear Bewildered,
Here are a few adjectives: cheap, tacky, stingy, and dumb as a box of hair. Toss in “classless” and “kooky” while you’re at it. Your in-laws aren’t fooling anyone—they’re pawning off their junk and pretending it’s generosity. How sad that they’ve chosen mildew and attic clutter over a real relationship with their grandchildren.

My advice? When their “gifts” arrive, don’t waste your breath. Drop them straight in the trash where they belong. And don’t let it ruin your holiday. Consider it comic relief—at least you’ll have a funny story for next year’s dinner table. Believe me, I once heard from a woman in Minnesota who got the same fruitcake back two years after she gave it!

You can’t buy love, but you sure can spot a cheap imitation. Enjoy your own family traditions, and let the tightwads keep their mildew.

— Ann Landers [a.k.a. ChatGPT]

Would you like me to also do a modernized version—the same snappy style, but framed more like today’s advice columnists (slightly less biting, slightly more “self-care” oriented)?

You Said:

Here’s one of the reader’s comments. What do you think of this idea?

Momma Reyes’s Comment: Dear Daughter-in-Law, what a crazy situation! What stood out to me was that you didn’t want to hurt your husband. I get that. I love my husband too. So let’s brainstorm some solutions because family is important and we know there are no perfect families. Here’s what I’m thinking. Continue to invite your in-laws for family occasions. Ask them, in lieu of gifts, to bring the birthday cake or dessert or side dish. Have them participate in some other way and let them know you’d prefer no gifts. In the end, the important thing is time spent together, not the gifts.

ChatGPT said:

That’s a thoughtful and very different take than Ann Landers’ blunt dismissal. A few observations on Momma Reyes’s comment:

1. Shift in Focus

Instead of zeroing in on the gifts (and their mildew), she’s redirecting attention toward building family connection. By asking the in-laws to contribute something practical like dessert or a dish, the focus moves from “What junk will they bring?” to “How can we share the occasion?”

2. Non-Confrontational

It sidesteps conflict. Rather than telling the in-laws “your gifts are insulting,” it reframes the situation as “we’d love you to contribute in a different way.” That’s less likely to bruise feelings, especially the husband’s.

3. Realistic Optimism

She acknowledges that families aren’t perfect and suggests working with what’s possible—accepting that the in-laws may never be the warm, thoughtful gift-givers one might hope for, but maybe they can still show up in small, useful ways.

4. Potential Pitfalls

If the in-laws are resistant to being more involved, this strategy could backfire (they might decline entirely rather than bring a cake).
It assumes they want to be helpful, when their history suggests avoidance.
It also doesn’t address the emotional insult of the past gifts—just avoids repeating the cycle.

Bottom line:
Momma Reyes’s suggestion is gentle, practical, and preserves dignity for everyone. It won’t fix the deeper issue of emotional distance, but it might reduce friction at family gatherings and give the children a better chance at seeing their grandparents in a positive role.

Would you like me to compare this “constructive compromise” approach side-by-side with Ann Landers’ “trash it and forget it” approach—so you can see the contrast in style and likely outcomes?

AI Conversations

recent posts