The Money You're Owed, and the Message You Keep Not Sending

"I'll send it tonight."

Your friend said it, and didn't. Add the refund a company promised in March and the deposit on the flat you left in the spring. Now you're owed a few hundred quid, with a low hum of irritation you've learned to ignore.

Why haven't you chased any of it? You can't remember the details, and chasing feels awkward.

AI's good at the first problem. The second stays yours, though it's easier with the facts in front of you.

Tonight, find what's outstanding

You can connect your email to AI so it can read your inbox, and then AI can search a year of email in a minute. If yours isn't connected, read what to check before you connect your email. Either way, keep it read-only, which means AI can look but can't send, delete or change anything.

Search my email from the last 12 months for money I may still be owed. That includes refunds I was promised, deposits due back, orders I reported as missing, and anything a company said it would "process" or "arrange". For each one, read the thread and tell me whether it was later resolved. List only the unresolved ones. For each, give the company, amount, what they promised, the date, any reference number, and a one-line quote as evidence. Don't send anything or change anything.

You'll get a short table, and some of it you'll have forgotten entirely.

Some of the table will be wrong, because AI only sees email. A thread that looks open may have been sorted on the phone, and promises made in a shop or a group chat won't appear at all.

Now and then AI even reads "We've processed your refund" as the promise, when in fact that line means the problem was sorted.

Before bed, check your own bank

First check whether the money arrived anyway. An emailed promise doesn't prove the money never came. Refunds land under odd shop names, arrive in two parts or go back to a card you've since cancelled.

For each item, open your banking app and search for the company and the amount. Do this bit yourself. Connecting your bank to a chatbot to save five minutes is a poor trade.

Cross off everything that arrived, and what's left is the real list, which is shorter and more annoying.

Tomorrow evening, one email per company

Companies respond to specifics, which means a date, an amount, a reference number and their own words quoted back. Last night's search pulled those out for you.

Draft a short, polite, firm email to [company] about [item]. Include the date they promised the refund, the reference number, and quote their own words back to them. Ask for the money within 14 days and a confirmation of when it was sent. No threats, no long story, under 120 words. Then tell me in one line what my options are if they don't reply.

Read the draft before you send it from your own inbox, and change anything that doesn't sound like you. Keep the one-line note on what comes next.

In the UK that's often a chargeback, where your card company takes the money back for you. Otherwise it's a complaint route the company has to tell you about.

Send one email per item, all in one evening. Most get paid within the fortnight, because specific emails get answers.

Later in the week, the friend

This is the one people most want help with, and it's also where AI should do least. Don't let AI search your texts for "I'll pay you back".

You know who owes you, but how to ask without costing the friendship is a judgement about someone AI has never met.

Use AI to get past the blank screen, and stop there.

My friend owes me [amount] from [what it was for] a few months ago. We're close and I don't want it to be a thing. Give me three ways to bring it up by text. Make one casual, one straight, and one that gives them an easy out if money's tight right now. Each under 40 words.

Pick the one that sounds like you, or more likely take half of one and write the rest yourself. AI's drafts drift towards a debt-collector tone if you let them, so keep the person in the message.

Then send the message from your phone, to your friend, in your words. If they're skint, you'll find out, and that's worth knowing too.

In a fortnight, let the small ones go

Anything still unpaid gets the next step from that one-line note. If there's a £4 item on the list, cross it off.

You set out to stop the hum, and nobody's keeping score.

AI remembers what you were promised. You decide who gets the message.