This A.I. sends the nasty emails you wish you could write

This A.I. sends the nasty emails you wish you could write

Yesterday I unleashed a tirade of abuse on my boss in an email. but I didn’t write a word of it. Instead I cc’ed my assistant Reginald into the conversation and he sent Boris the following:

Thank you, Martin (moving to bcc).

Now then, Bruno, was it?

I hope this electronic letter finds you well, you frumpy-assed dilettante. I’ll assume that your ill advised passive aggressiveness is coming from a place of self wrought inadequacy, so in this regard, you shall pass by a narrow margin.

But heed my words sir, this arena is no place for amateurs and children. It would find you well to shut your mouth you no brained, illiterate, oxygen thieving germ. I shall henceforth be contacting your superiors to scold them for their egregious blunder, in giving you a position at this sub par place of employment.

Ta ta,


Reginald is an A.I. (or more specifically a bot) designed to handle email conversations you’ve had enough of.

He’s the creation of one Gabriel Whaley as a reaction to those ’email virtual assistants’ that can schedule calendar appointments for you.

“A colleague was trying to schedule a meeting with a connection from LinkedIn, and that connection handed her off to ‘Andrew’ – her personal AI assistant from,” he says. “This felt passive and pretentious, which it was and is totally something will have to figure out. The two ended up not meeting, because of how uncomfortable this made my colleague.

“I actually found it hilarious that this dynamic actually resulted in not meeting. And it made me think further – as we further automate parts of our lives, I imagine we will get to the point where we create programs that do our dirty work for us as well.”

As a result, Reginald was born. Simply cc [email protected] in your email and ‘your assistant’ will move you to BCC and start a foul-mouthed conversation with the person who has annoyed you. It works with humans and virtual assistants alike.

Whaley says Reginald was easy to set up. “It’s currently a pile of standard ‘if’ statements based on keywords/phrases that I pre-selected… Now I’m collecting data to feed into an algorithm that should eventually be able to respond appropriately to most email situations (although – detecting passive aggression correctly has been pretty tricky).”

Reginald should stand up to heavy usage but some of the replies may take a bit longer to come through if he becomes popular. He’ll even continue the conversation if your target replies.

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Just be careful with whom you try it. Luckily Boris has a sense of humor so I wasn’t fired, but it did leave him a bit confused as to what the hell was going on.

➤ Reginald

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