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That email you've been dreading? Let AI write the first draft

Issue #1 · By Dontè

Hi friend,

We all have one. The email to a landlord about the broken heater. The "sorry I went quiet" text to an old friend. The polite no to a favor you really can't do. It sits there for days, not because it's hard, but because finding the right words feels like a chore.

Good news: this is one of the things AI is genuinely great at. You tell it what you want to say, and it hands you a clean, friendly draft you can tweak and send. Here are three free tools to try, from easiest to most powerful.

1. Microsoft Copilot: easiest to start

copilot.microsoft.com

If you use a Windows PC or the Edge browser, Copilot is probably already a click away. The free version handles chat and writing help. There are usage limits, but for a few emails a day you're unlikely to hit them.

Best for: people who want zero setup.

2. Google Gemini: great if you already use Google

gemini.google.com

Free with any Google account. One heads-up: as of October 9, 2026, free users only get Google's lighter "Flash-Lite" model, and the stronger ones now need a paid plan. For everyday emails and texts, the free version is still plenty.

Best for: people who already have a Google account.

3. ChatGPT: most powerful free option

chatgpt.com

ChatGPT's free plan now includes unlimited text chats, so you can ask for as many drafts and rewrites as you want ("shorter," "warmer," "less apologetic"). Things like file uploads and voice chats are limited on the free plan, but you won't need those for writing messages.

Best for: going back and forth until it sounds exactly like you.

Try this prompt (copy and paste)

I need to write a [email / text message] to [who it's for]. Here's the situation: [explain in a sentence or two]. What I want to say is: [your main point]. Keep it [friendly / professional / short], sound like a real person, and keep it under 120 words. Then give me one shorter version too.

Fill in the brackets, paste it into any of the three tools above, and you'll have two drafts in seconds. Don't love it? Just reply "make it warmer" or "less formal" and it'll try again.

One mistake to avoid

Don't hit send without reading it out loud. AI can sound a little stiff, add details you never mentioned, or get a name or date wrong. Read the draft once, fix anything that isn't true or doesn't sound like you, and then send. Also skip pasting in private info like account numbers or passwords. The AI doesn't need them to write a good message.

That's it for this week

Pick one message you've been putting off and try it today. I'd love to hear how it went, so just hit reply.

Next week: planning a week of meals and a grocery list with AI in five minutes.

Talk soon, Dontè, Ask It Simply

Sources: ChatGPT plans and pricing · Google Gemini plans · Gemini Apps limits

P.S. Know someone who's been "meaning to try AI"? Forward this to them.

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