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Home / Features / I let AI reply to my emails in my style for 24 hours, here’s how it went

I let AI reply to my emails in my style for 24 hours, here’s how it went

A custom ChatGPT looked at a stack of emails I sent to get my style. I then let it write replies for me for 24 hours.

ChatGPT writing emails on iMac

People are running wild with AI, outsourcing it to do all manner of things on their behalf. It was only a matter of time before we started using AI systems like ChatGPT to write emails.

In fact, there are a few email apps that are starting to trickle out AI writing features. Some are smarter than others, picking up on your writing style, but they’re all a bit broad. What if you could have a hyper personalised chatbot to help with your emails?

Since there are few things more monotonous than tapping out replies, I built a custom ChatGPT bot that could reply to emails for me. I gave it a stack of my sent emails (I’m sure there’s nothing that could go wrong with that…) so it could learn how I write and gain some context behind what’s normally in my inbox. After that, I tasked it to replying to emails for me. Here’s what happened in the 24 hours I used it.

“Sent from AI”

So the first thing to do was build the custom chatbot that can reply to my emails. Thanks to ChatGPT, you can build mini custom chatbots to fulfil a specific purpose. Part of the training process here was to feed the AI a bunch of replies I’d sent in the past, so it could learn the way I write. Since I’m not totally unhinged, I hand-picked a variety of examples that had nothing too personal in them. Hopefully, this helps the chatbot to be more versatile and write better responses, no matter what I throw at it.

Unfortunately, there’s a bit of manual work to be done here. I have to paste each email I get into the ChatGPT bot, and then copy the response out back over to Gmail. It’s certainly not as sleek as using some swish new email client with AI built in, but hopefully the personalised angle can make me overlook that.

Screenshot to build the ChatGPT to reply to emails

Then it came time to use the AI email bot… and things took a slight turn. I can’t show a lot of the responses it wrote due to embargoes and various other reasons, but I’ll do my best to pick out some of the key quirks of the chatbot. It managed to get my greetings right, and was good at matching it to the context of the email. “Hey” when it can be more casual, or a “Good morning” if it’s something more formal. The same can be said about the sign-off, typically opting for “Best, Connor”.

But it couldn’t quite handle writing the actual email. You could instantly tell that the email was following some sort of template. It would essentially repeat what the email said, usually with a “Thanks for telling me about…” slapped on the front. It would often times sound too keen or excited, and write 20 words where 5 or 6 would do. Ever got a spam email you thought was written by AI? That’s exactly what this sounded like, just with a sprinkling of how an email from me might look.

This isn’t the email-beating hack I hoped for

It was somewhat disappointing that this custom chatbot couldn’t write emails for me. Even with about 50 samples given to the bot at the start, it still couldn’t stray away from sounding generic and like it was written by a chatbot. As with any AI, the more data you give it, the better it will be. Perhaps I could retrain the chatbot with hundreds of email samples? But then it becomes a bit too impractical, it would be easier to just reply myself.

So for now, if you get an email from me, you can rest assured that I did actually write it. Perhaps an email client will come around where it can read all of your replies and sound a bit like you. But AI isn’t quite the email-beating hack I hoped for just yet.

Profile image of Connor Jewiss Connor Jewiss


Connor is a writer for Stuff, working across the magazine and the Stuff.tv website. He has been writing for around seven years now, with writing across the web and in print too. Connor has experience on most major platforms, though does hold a place in his heart for macOS, iOS/iPadOS, electric vehicles, and smartphone tech. Just like everyone else around here, he’s a fan of gadgets of all sorts! Aside from writing, Connor is involved in the startup scene. This exciting involvement puts him at the front of new and exciting tech, always on the lookout for innovating products.

Areas of expertise

Mobile, macOS, EVs, smart home

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