What can I ask ChatGPT? 20 plain-English prompts to start with on day one
You can ask ChatGPT to draft an email, prepare questions for a doctor's appointment, simplify a confusing letter, suggest a recipe from what is in your refrigerator, translate a sentence, or help you start a difficult piece of writing. Twenty plain-English prompts are below — copy any of them and type it into the box on the same day you sign up.
The single most common reason people quit ChatGPT in the first week is the empty box. The blinking cursor. The faintly accusatory blank space — and the moment of complete blankness that follows. The people who type a real question in the first five minutes are the ones still using it a year later. The people who sit staring at the box close the tab and never come back.
So this piece is the list I have learned to hand people before we sit down. Twenty prompts. Each one is a sentence you can type, exactly as written, on day one. Each one produces an answer that is useful inside about thirty seconds. The point is not that these are the only twenty things ChatGPT can do — the point is that the first question only has to happen, and after it happens, the rest gets easier.
Group one — Writing things that are hard to start
These are the prompts that account for, in the AARP's 2024 Tech Trends report on adults 50 and older, the largest share of how older adults actually use generative AI. The hardest sentence in any letter is the first one. ChatGPT will not write better than you. It will give you a draft you can edit into your own voice, which is the difference between staring at a blank page and rewriting a serviceable one.
1. Draft a thank-you note. Help me write a four-sentence thank-you note to my neighbor Carol, who brought a casserole during a difficult week. Keep it warm but not gushing.
2. Write a stiff but polite letter. Help me write a polite letter to the property manager about a faucet in the kitchen that has been leaking for three weeks. Firm tone, not angry.
3. Draft a difficult email. Help me write a short email to my brother declining his invitation to Thanksgiving, in a way that is honest but does not start a fight.
4. Start a eulogy or wedding toast. Help me write the opening paragraph of a five-minute eulogy for my older cousin, who was a postal carrier for thirty-six years and liked vintage cars. I will edit the rest.
5. Rephrase something that sounds wrong. Read this sentence and tell me three ways to say the same thing in plainer English. Then paste your sentence.
Group two — Doctor's appointments
This is the use case I quietly believe is the single most valuable thing ChatGPT does for anyone over 65. According to the Pew Research Center's March 2024 survey on ChatGPT usage, only a small fraction of adults 65 and older have tried the tool for this purpose, and the ones who have tend to say the appointment that followed was different — calmer, more thorough, less rushed — than the one before.
6. Prepare questions for a specialist visit. I am 74. I have type 2 diabetes, diagnosed six years ago. My A1C at the last visit was 7.2. I see my endocrinologist next Tuesday. Help me prepare seven questions to ask, in order of importance.
7. Understand a new diagnosis in plain English. My doctor said I have something called atrial fibrillation. Explain what that means, in plain English, in six sentences, as if you were a thoughtful family friend who happens to be a nurse.
8. Compare two medications already prescribed. My doctor has me on metoprolol and is considering switching me to bisoprolol. What is the practical difference between the two? What questions should I ask before agreeing?
9. Prep a script for a difficult call. Help me prepare what to say when I call my insurance company tomorrow morning about a claim that was denied. I need them to reconsider it. Three short paragraphs, polite but firm.
Note the rule that applies to every prompt in this group: ChatGPT is upstream of your doctor, not a substitute for one. The answers help you ask better questions. The answers are not the answer.
Group three — Paperwork that arrives in the mail
The insurance company sends a four-page letter. The Medicare statement looks like a bank ledger. The HOA notice is written in legalese. The lease addendum has fourteen paragraphs and the one that matters is somewhere in the middle.
10. Simplify a long letter. Explain the attached letter in plain English in five sentences. Then tell me what, if anything, I have to do. Paste only the readable paragraphs — no policy number, no Social Security number, no full name and address. (More on what never to paste is in the safety piece.)
11. Translate a Medicare summary. I am going to paste a Medicare Summary Notice. Explain in plain English what each charge is for, which ones were paid by Medicare, and which ones I still owe.
12. Decode a legal-looking paragraph. Read this paragraph and tell me, in plain English, what it is asking me to agree to. Then list the three things I should ask a lawyer before signing.
13. Compare two written quotes. I have two written estimates for the same roof repair. Help me make a side-by-side table comparing them on price, materials, warranty, and timeline.
Group four — Cooking and the kitchen
This is the gentlest use case and the one most people enjoy first. ChatGPT will not be the best recipe you have ever cooked. It will be a usable one, at six in the evening, with what you actually have in the refrigerator.
14. Cook from what is on hand. I have one chicken breast, a can of black beans, half a yellow onion, two cups of rice, and a half-empty jar of salsa. I do not feel like going to the store. What can I make in under thirty minutes?
15. Adapt for a health condition. I have high blood pressure, so cut the salt in this recipe by two-thirds and tell me what to use instead. Keep the flavor close to the original.
16. Scale a recipe down. This recipe serves eight. I am cooking for two. Rewrite the ingredient list with the smaller amounts already done, so I do not have to do the math.
17. Make a grocery list from a week of dinners. Here are seven dinners I want to cook this week. (List them.) Make me one consolidated grocery list, organized by section of the store — produce, meat, dairy, pantry.
Group five — Translation, family, and the small useful things
18. Translate a note from a piano teacher. Translate this Spanish note into plain English, and tell me what the teacher is actually asking me to do. Then paste the note.
19. Help with a grandchild's homework, without doing it for them. My grandson is in fifth grade and stuck on a word problem about fractions. The problem is below. Walk me through how to explain it to him without giving him the answer.
20. Look up the word you can't remember. I am trying to remember a word that means "the feeling of being homesick for a place you have never actually lived." Five sentences explaining what the word is and how it is used.
How to use this list on day one
The honest workflow for day one of ChatGPT is small. Sign in, which I wrote out step by step in a separate piece. Open the box. Pick one prompt from this list — the prompt that sounds most like something you would actually need today, not a test question. Type it in. Press Enter. Read the answer.
That is the whole assignment for day one. One real answer to one real question. The reason this works is that one usable answer makes the tool feel real in a way that ten test questions never do. Test questions get test answers. Real questions get real ones, and the real one is the moment the tool stops being abstract and becomes a thing on your desk you can use.
A note on the printed version: because the screens shift every few months, and because most people in this age range learn better from a list they can keep next to the keyboard than from one they have to scroll back up to find, the twenty prompts above are reprinted on a single page in our binder, in the same order, on the kind of paper that lays flat next to the computer. It is part of the $19 setup binder we ship to your door. None of this is secret. It is just useful to have it on paper at the moment you need it.
FAQ
What is the best first question to ask ChatGPT?
The best first question is one you actually wanted the answer to before you opened the tab. The most common useful first question for adults over 65 is: Help me prepare four questions to ask my doctor about my blood pressure medicine at my appointment this week. It produces a list, it is genuinely useful, and it takes about thirty seconds. Test questions are the wrong way to start — they produce test answers that do not help you decide whether the tool is worth keeping.
Are there things I should never ask ChatGPT?
You should never paste in your Social Security number, bank account numbers, passwords, full medical records with identifying information, or anything that identifies a minor in your family — their full name, school, address, or daily schedule. Helping a grandchild with homework is fine. Pasting in their full name and the name of their school is not. The full safety list is in the safety piece.
Can ChatGPT answer questions about current events?
Not reliably. The free version of ChatGPT has a knowledge cutoff — the date after which it does not know what has happened. In mid-2026 that cutoff is sometime in early 2026 for the standard model. For yesterday's news, today's weather, or this week's election results, use a news website. ChatGPT is for writing tasks, not for current events.
Will ChatGPT remember what I asked it yesterday?
By default, no. Each new conversation starts fresh. If you started a chat last Monday and you start a new chat this Tuesday, ChatGPT has no memory of Monday's conversation unless you have turned on the memory feature in settings. For most adults over 65, leaving memory off and pasting the relevant context at the top of a new chat is the simpler model.
Can I ask ChatGPT for medical or legal advice?
You can ask it to help you prepare questions for a doctor or a lawyer. You should not ask it to replace one. ChatGPT does not know your specific health history, your specific contract, or your specific situation — and every real medical or legal question has details the tool does not know and cannot ask the right follow-up questions about. A doctor can. A lawyer can. ChatGPT is upstream of them, not a substitute.
How long should the prompts be?
A useful prompt is usually three to five sentences. The first sentence is the task. The second is the relevant context — your age, your situation, what you already tried. The third is the constraint — how long, what tone, what to leave out. Short prompts get vague answers. Five-paragraph prompts confuse the tool. Three to five sentences is the sweet spot.
What if the answer is wrong?
Some of the time, it will be. ChatGPT can be confidently and fluently wrong, especially about facts that have to be exactly right — a phone number, a date, an address, a price. The rule is: use the writing, check the facts. If the answer is a thank-you note, use it. If the answer is a phone number for a federal agency, look it up on the official website before you dial. The wider explanation of why this happens is in the safety piece.
What's striking is that one usable answer on day one — a thank-you note that gets sent, an appointment that goes better than usual — is often what moves the tool from abstract to indispensable. If you want the one-page version with the twenty prompts printed on it, it's the free plan. If you want the full setup binder on your desk before the weekend, it's $19. And if you haven't actually signed up yet, the numbered walkthrough is here.
— Shawn Ivie Founder, Plain English Company