Chat GPT Speed Dating
HOW TO TRAIN AI
Most agents pop into ChatGPT or Claude or Perplexity, toss out a request to write something, get an answer, and decide AI just “doesn’t work because it doesn’t sound like them.”
Here’s the deal — AI isn’t psychic. It’s a mirror, so…… what you put in determines what you get out.
Garbage in = garbage out. Sort of like speed dating. In speed dating, a lot of questions are asked so you can quickly get to know the person on the other side of the table, right?
Think about your closest friends. They can finish your sentences because they know you— your tone, your humor, your pet peeves.
Now imagine meeting someone at a coffee shop and expecting them to know and understand you in the same way as your inner circle, after just two minutes of small talk. Sort of ridiculous, right?
AI is the stranger at the coffee shop that can quickly become your best friend if you ask the right questions and deliver the right answers during your speed dating. That’s exactly what I’m going to show you how to do here.
Let’s Cozy Up to AI
If you want AI to sound like you — to really get you — you have to spend a little time together.
You have to show it how you talk, what you care about, and how you do business.
That’s where ChatGPT Speed Dating comes in.
It’s your onboarding conversation — a quick but meaningful “get to know me” session so AI can start sounding less like a stranger and more like your business partner.
When you take the time to train it — to feed it the right context, examples, and boundaries — it becomes the most scalable assistant you’ll ever have.
I’M REBECCA
Nice to Meet You.
Chat GPT + I are old friends.
Excited for you to get to know eachother
Rules of Engagement
You want Chat GPT to remember your “conversations” for future use. Here are the steps to take to be sure that happens.
Check if Memory Is On
Click your name or profile icon (bottom left on desktop or top right in mobile app).
Select Settings → Personalization → Memory.
Make sure the toggle is ON.
If it’s off, ChatGPT forgets everything when you close the chat.
If it’s on, it can remember facts you share (your name, role, style, business details, preferences, etc.) and apply them automatically later.
How to Teach It What to Remember
You can literally say things like:
“Remember that I’m a real estate agent in Oregon and Washington.”
“Remember that I prefer short, direct writing with no fluff.”
ChatGPT will confirm:
“Got it! I’ll remember that.”
That means it’s stored in your memory profile and will apply across future chats — not just the one you’re in.
How to Check or Edit What It Knows
Go to Settings → Personalization → Manage Memory.
You can view what ChatGPT remembers, delete specific items, or clear everything.
If something feels off, just say:
“Forget that I’m in Oregon,” and it’ll erase that memory.
What Memory Doesn’t Do (Yet)
It doesn’t automatically “save” your whole conversation text.
It only remembers key facts or patterns it’s explicitly told to store.
If memory is off, ChatGPT resets every time — no continuity between chats.
Voice Users: Same Rules Apply
If you’re using voice mode, ChatGPT can still learn from what you say, as long as memory is enabled.
Speaking naturally helps it understand your tone and phrasing, which strengthens how it mirrors your style later — but it won’t “record” or store audio; it simply remembers the details you provide.
📌Pro Tip #1
After you finish your ChatGPT Speed Dating session or any important session, say or type:
“Remember everything you’ve learned about my voice, tone, and market so you can apply it in future chats.” OR
“Remeber these specific details from this chat so you can apply it in future chats.”
And then list the details. You’ll get a confirmation — that’s your signal that it’s saved.
📌Pro Tip #2
Type your name, market, and title into ChatGPT and say:
“Tell me what you know about this person.”
After you read the results, then ask:
“Is this person a good real estate agent?”
Read that response and then….
“I am this person. How can I improve my presence online and in AI search results?”
Your new friend is going to give an unbiased answer. Pay close attention to this! You’ll get a clear picture of how you show up online and in AI searches — what’s consistent, what’s missing, and where you could be more visible. You’ll use this information to create your to-do list, and once ChatGPT knows you better, it’ll be able to help!
The Prompt
You’re going to help ChatGPT get to know your voice, goals, and vibe — plus you are setting the stage for what questions the chat should ask you in order to best do that. Answer thoughtfully. Be honest. Be detailed. The more you share, the more useful it becomes.
Copy and paste everything below into a new ChatGPT chat. This is your first “date.”
I want you to act as my creative, strategic writing and business partner.
Before we start creating content, I want you to get to know my tone, my market, and my personality.
Think of this as “Speed Dating” — your goal is to learn how I talk, what I value, and who I serve so you can write, plan, and strategize like me, not every other agent online.
Here’s what I want you to do—
Ask questions first. Start with 10–15 open-ended questions that help you understand how I sound, who I serve, and what I stand for.
Study my tone. Ask for examples of my writing (emails, bios, social posts, listing descriptions) so you can analyze my word choice and rhythm.
Clarify preferences. Ask how I feel about emojis, exclamation points, and punctuation style.
Find my boundaries. Ask what phrases or tones I hate so you can avoid them.
Uncover intent. Ask about my business goals, audience, and where my content will live (Instagram, newsletter, blog, etc.).
Summarize. Once we’ve talked, summarize what you’ve learned about my voice, values, and goals — and confirm with me before writing anything.
Think of this as building a relationship. It’ll take a few rounds of honest conversation before we click, but once you get me, I’ll use you for everything from listing descriptions to full-blown marketing campaigns.
Start by asking me your first 7–10 questions to get to know my business, tone, and goals.
Voice Command
If you’d rather talk than type, use ChatGPT’s voice command feature instead of copy-pasting the prompt.
How to do it:
Open the ChatGPT mobile app (voice input isn’t available on desktop yet).
Tap the microphone icon and say the same instructions you’d normally paste.
Answer ChatGPT’s questions out loud, just like a real conversation.
Why it works:
Most people write more formally than they speak. When you use voice, ChatGPT picks up on your natural tone, rhythm, and pacing — how you actually phrase things, what words you emphasize, and where you pause or get animated.
That subtle context helps it mirror your personality more accurately in future writing.
If you sound better out loud than on paper, start here. It’s faster, more natural, and helps ChatGPT learn your real voice — literally.
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