Start with a direct, unemotional message

The fastest way to get paid is to ask once, clearly, without anger or apology. Send a message—text, email, or in person—that states the amount, what it was for, and when you expected payment. Do not soften it with "I hate to bother you" or "whenever you get a chance." Those phrases signal that the debt is optional.

Use a sentence like: "You borrowed $200 for groceries on March 15. I need that back by March 29." If it was a loan with no agreed date, pick a reasonable one—usually within two weeks of the original conversation. Write it down so there is a record, even if you spoke in person first.

Do not ask why they have not paid yet. That opens a conversation instead of closing one. You are not investigating their finances or their character. You are stating a fact and naming the deadline.

Key Takeaways

  • State the amount, the date borrowed, and the repayment deadline in your first message, with no apology or explanation of why you need it.
  • Give a specific date two to four weeks away, not "whenever you can" or "no rush"—vague timelines let debts drift.
  • If they miss the deadline, send one follow-up message within a week, then decide whether to pursue it further or let it go.
  • For amounts under $500 and people you want to keep knowing, small claims court is usually not worth the filing fee and time.
  • Keep all messages and any written agreement, because you will need them if the debt becomes a legal matter.

What to do when they miss the first deadline

Wait three to five days after the deadline passes, then send one follow-up message. Keep it short: "I have not received the $200 yet. Can you send it by [new date, usually one week away]?" Do not accuse them of forgetting or lying. Assume they are busy or short on cash.

If they respond with a reason—job loss, unexpected bill, medical expense—you now have information. You can decide whether to extend the deadline, accept a partial payment, or set up a payment plan. If they do not respond at all, you have your answer: they are avoiding you.

After the second deadline passes with no payment and no message, send one final message: "I need to know your plan for repaying this. Please let me know by [date]." Then stop. You have asked twice. A third ask becomes nagging, and nagging does not make people pay—it makes them avoid you harder.

When to involve a written agreement

If the amount is large (over $500), if it is a loan between family members who have a history of money conflict, or if the borrower asked for time to pay, put the terms in writing before you hand over the money. This is not insulting—it is protecting both of you.

A simple text message counts as a written agreement: "I am lending you $1,000 for your car repair. You will pay me back $250 on the 15th of each month for four months, starting April 15." If they agree by text, you have a record. If they do not agree, you know before you lend.

For loans between family members or close friends, a handwritten note signed by both of you works just as well as a formal contract. It does not need legal language—just the amount, the date, the repayment terms, and both signatures. Keep it somewhere safe.

How much effort is worth the amount owed

If someone owes you $50 and you have to spend three hours chasing them down, you have lost money in time. Before you send the first message, decide what you are willing to do to collect. Will you ask twice and then let it go? Will you pursue it to small claims court? Will you ask a mutual friend to intervene?

Small claims court costs between $50 and $300 to file, depending on your state and the amount. You also have to take time off work to appear. For debts under $500, the math usually does not work unless you are very angry or the person has a pattern of not paying.

If the person is a close friend or family member and the amount is small, you may decide the relationship is worth more than the money. That is a valid choice—just make it consciously, not by accident. Say to yourself: "I am choosing to let this go," rather than letting it fester.

What to do if they refuse to pay or disappear

If someone says they will not pay, or if they stop responding to messages, you have a few options depending on the amount and your relationship. For small amounts (under $200), you can write it off, block them, or ask a mutual friend to pass along a message. For larger amounts, you can pursue small claims court, send a demand letter, or report the debt to a credit bureau if the person is a business.

A demand letter is a formal written request for payment, usually sent by mail or email. It states the amount, the date it was owed, and a final deadline (usually 10 to 30 days). You can write one yourself or pay a lawyer $100 to $300 to write it. A demand letter does not force payment, but it creates a paper trail and sometimes shocks someone into paying.

Small claims court is an option if the amount is within your state's limit (usually $5,000 to $25,000) and you have a record of the debt. You file paperwork, pay a filing fee, and appear before a judge. If you win, you get a judgment—a court order saying they owe you. Collecting on that judgment is a separate process and is not may provide.

How to avoid lending money you cannot afford to lose

The simplest way to handle a debt that goes unpaid is to never make the loan in the first place. Before you lend money to anyone, ask yourself: "If I never see this money again, will my life be okay?" If the answer is no, do not lend it.

This is not cynical. It is realistic. People borrow money with the best intentions and then life happens—job loss, illness, a bigger emergency. They may feel too ashamed to tell you, so they avoid you instead. You cannot control their choices, but you can control whether you put yourself in a position where their choices hurt you.

If someone asks to borrow money and you want to help but cannot afford to lose it, offer an alternative: a smaller amount, a gift instead of a loan, help finding a low-interest personal loan, or a connection to a community resource. You can be generous without being reckless.

Frequently Asked Questions

Should I ask in person, by text, or by email?

Text or email is better because you have a record. In-person conversations are easy to misremember or deny later. If you have already asked in person, follow up with a text or email that says: "Just confirming—you owe me $300 by March 29." That creates a paper trail.

What if they say they will pay but keep missing the deadline?

After two missed deadlines, they are not going to pay without outside pressure. Stop accepting new promises. Ask for a payment plan with specific dates and amounts, or ask for partial payment now. If they refuse both, you know the money is gone.

Can I charge interest on a loan to a friend?

You can agree to any interest rate you both accept, but it must be in writing before you lend the money. Some states cap interest rates on personal loans, so check your state's law. For small loans between friends, interest often makes things awkward—a flat fee or no interest is more common.

What if I lent money to someone years ago and they still have not paid?

Most states have a statute of limitations on debt collection, usually between three and six years. After that time passes, you generally cannot sue. If you want to pursue it, check your state's rules. Otherwise, the debt is old enough that pursuing it will damage the relationship more than the money is worth.

Should I ask a mutual friend to help collect the debt?

Only if the person is avoiding you and the amount is significant. A mutual friend can pass along a message or confirm that the person is dodging you, but they cannot force payment. Using a third party can also make the situation more tense, so use it as a last resort before small claims court.