When someone doesn’t pay you back

The short version

Work out the exact figure, itemize it, send it in one message, and ask once. Do not apologize for asking and do not explain why you need the money. Both of those turn a piece of information into a conversation, and the conversation is the thing you have been dreading for two weeks.

If it does not arrive, offer to split it into three rather than asking again. If it still does not arrive, decide whether the amount is worth more to you than the friendship, and if it is not, write it off properly and stop covering things for that person. Those are the only three moves there are.

Why the vague version fails

Nobody plans to not pay someone back. It happens because the amount was never stated, so it never became a specific thing either person could act on. You remember covering the tickets. They remember getting the coffees. Neither of you has a number, and in the absence of a number the honest position is genuinely unclear to both of you.

Which is why the reply to a vague ask is almost always a vague offer. Someone who thinks they owe “about a hundred and fifty” will send a round $150, and on the numbers below they would be $9.05 short. Not enough to raise, which means it stays with you, which means the thing you did to avoid an awkward conversation cost you nine dollars and did not remove the awkwardness.

Get the exact number

This is the case that makes it hard, and it is the normal one: no single loan, just five ordinary occasions over two months, one of which they paid for.

Which comes to $159.05. Three things about that number are worth noticing, because they are what makes it work:

• It is not round. A precise figure reads as something you worked out. A round one reads as something you estimated, and an estimate can be argued with.
• It includes the coffee they bought. Netting off the thing they paid for is what turns the message from a demand into an account. It also costs you almost nothing and buys you the whole tone of the conversation.
• The present is split three ways, not two. Getting that right matters more than the $7.50 it is worth, because one line they can correct is one line that puts the whole list in question.

What to actually send

One message, the figure first, the list under it, and a closing line that gives them a reason to do it now rather than an obligation to explain themselves.

Send it to them directly, not to a group. A group message about money is a message about someone in front of an audience, and the person in it will feel the audience before they read the number.

Write yours

Put in what you covered. The total is worked out on the numbers, and the message is written for you underneath, ready to copy.

Hey, could you send me $159.05 when you get a chance?

It comes to:
- Concert tickets: $90.00 (half of $180.00)
- Dinner after: $47.25 (half of $94.50)
- Taxi home: $16.00 (half of $32.00)
- Leaving present: $15.00 (1/3 of $45.00)
- Less Coffee: $9.20

No rush, just easier to sort while we both remember what it was for.

If it is a group rather than one person, the figure to ask each of them for is not their share of every expense but one net number each, which is usually far fewer payments than anyone expects. The fewest payments that settle everyone up has that method, and how to split shared costs fairly covers getting the shares right in the first place, which is what stops you being here again.

If nothing happens

Do not ask again the same way

A second identical message reads as pressure and gets the same result. Reply to your own message with the figure again and add the option of paying in parts. Someone who has not sent $159.05 in six weeks quite often cannot send it in one piece, and $53.02, then $53.02, then $53.01 is something they can say yes to without having to admit that.

Note that those three do not divide evenly, and that the odd cent goes on the first payment rather than being lost. If you are going to offer installments, offer ones that add up.

Decide, then actually decide

If it still does not come, the choice is to keep pursuing it or to write it off, and the failure mode is doing neither. A debt you have privately forgiven but still count costs you every time you see them: you have paid the money and kept the resentment. If you write it off, say so, and mean it.

What should change is not the friendship but your own habit. The person who does not pay you back is usually not a villain and usually will not become a better payer. Stop being the one who covers things for them, and the problem does not recur.

Not being here again

The reason $159.05 was hard to ask for is that it took two months and five occasions to build. By the end, neither of you could reconstruct it from memory, so the number had to be assembled before it could be requested, and assembling it was the part you kept putting off.

Three habits remove almost all of this:

• Write it down at the time. Thirty seconds when you tap the card, rather than an evening with a card statement two months later.
• Settle small and often. The same five items asked for in the week they happened are four requests for under fifty dollars each, and nobody finds those difficult.
• Let both directions show. When the record also shows what they covered, asking is not a claim about their character. It is reading out a balance you can both see.

Common questions

The figures in this article were produced by running Halvy’s own split engine on the worked example, which is why the installments add back to the cent. Nothing here is legal advice: rules on recovering money owed between individuals, including time limits, differ by country and by state, so check what applies where you live before relying on any of it.