Start with a written record of what was lent or owed

Before you ask for payment, have something in writing that shows the debt exists. This might be a text message where the person acknowledged borrowing money, an email confirming the loan terms, a receipt from a shared expense, or even a straightforward note you both signed at the time. If nothing exists yet, send a message now that says what was lent, when, and what you expect back — something like "Hi, just confirming I lent you $500 on March 15 for the car repair, and we agreed you'd pay me back by April 15."

This written record protects you if the conversation becomes difficult later. It also gives the borrower a chance to correct you if there's a misunderstanding about the amount or terms. Many people will pay once they see the debt documented clearly — they may have straightforward forgotten or lost track of time.

Key Takeaways

  • Have written proof of the debt before you ask — a text, email, receipt, or note that both of you acknowledged.
  • Ask directly and specifically: state the amount, when it was lent, and when you expect payment, without accusation or emotion.
  • Give a reasonable important date and explain why you need the money back if that's relevant to your situation.
  • If the person avoids you or refuses, decide whether small claims court, a written demand letter, or accepting the loss makes sense for the amount involved.
  • Never lend money you cannot afford to lose, because collection is slow, costly, and often unsuccessful between people who know each other.

Ask directly, name the amount, and set a important date

Contact the person in a way that creates a record — text, email, or a phone call you follow up in writing. Be specific and unemotional. Say: "I need to ask you about the $500 I lent you on March 15. I'd like you to pay me back by April 30. Can you let me know if that works for you?" Do not accuse, shame, or assume they are avoiding you. Many borrowers genuinely forget or are embarrassed and need a direct prompt.

The important date matters. Without one, the conversation stays open-ended and the person has no reason to prioritize your money over other bills. A important date also shows you are serious. Make it reasonable — two to four weeks is standard for personal loans, longer if the person is in genuine hardship.

If the person says they cannot pay by that date, ask when they can. Get a new date in writing. If they say they will pay but do not, you now have a pattern of broken promises, which matters if you later pursue the debt in court.

Explain why you need the money if it affects your situation

If you lent money because you had it to spare, you do not need to explain. But if you lent it because you were helping someone out while managing your own tight budget, say so. "I lent you this money because I wanted to help, but I'm counting on getting it back to cover my own bills" is honest and often reminds the borrower that this is not a gift.

Do not use guilt or emotional pressure as a tactic — it usually backfires and makes the borrower defensive. Stick to facts: you need the money, you set a important date, and you expect them to meet it.

What to do if they avoid you or say no

If the person stops responding to messages, sends vague promises without following through, or outright refuses to pay, you have three realistic options depending on the amount and your relationship.

Send a written demand letter. This is a formal but not legal document — a letter that states the debt, the important date you gave, and that you expect payment within a final important date (usually 10 to 30 days). You can write this yourself or use a template online. Send it certified mail so you have proof of delivery. Many people take a demand letter seriously because it signals you are willing to escalate. Keep a copy for your records.

File in small claims court. If the amount is under your state's small claims limit (usually $5,000 to $10,000), you can sue without a lawyer. You file paperwork with your local court, pay a filing fee (typically $50 to $300), and the court schedules a hearing. You present your written evidence — texts, emails, the demand letter — and the judge decides. If you win, you get a judgment, but collecting it is still your problem. The person may ignore it, and you may need to pursue wage garnishment or bank levies, which is expensive and slow. Small claims makes sense if you have clear proof and the amount is large enough to justify the time and cost.

Accept the loss. If the amount is small, the relationship matters to you, or you have no proof, you may decide it is not worth the time and stress. This is a legitimate choice. Some people lend money knowing they may not get it back — that is the real cost of the loan.

How to avoid this situation with future loans

Never lend money you cannot afford to lose. This is the single most important rule. If you lend $500 and never see it again, can you absorb that? If not, do not lend it.

Before you lend, discuss repayment terms out loud: the amount, when it is due, whether there is interest, and what happens if the person cannot pay on time. Write these down and both keep a copy. If it is a large amount or a family member, consider putting it in a straightforward written agreement that both of you sign — this is not cold or legal, it is clear.

If someone asks to borrow money and you are unsure, say no. You do not owe anyone an explanation beyond "I cannot lend that right now." Protecting your own finances is not selfish.

When the debt is with a business instead of a person

If a business owes you money — a contractor who did not finish a job, a vendor who overcharged you, a service provider who took your payment and did not deliver — the process is similar but you have more leverage. Document everything: emails, receipts, photos of incomplete work, screenshots of promises made.

Send a written demand letter to the business owner or manager, not just a customer service email. State what was owed, what you paid, what was not delivered, and give a important date for refund or completion. Many small businesses respond to a formal letter because they want to avoid court and bad reviews.

If the business ignores you, small claims court is more practical than it is with individuals because businesses are easier to locate and serve with paperwork. You can also file a complaint with your state's attorney general, the Better Business Bureau, or your credit card company if you paid by card — the card company may reverse the charge through a chargeback process.

Frequently Asked Questions

Can I charge interest on money I lent to a friend?

You can, but it changes the nature of the loan and may damage the relationship. If you want interest, discuss it before you lend and put it in writing. State laws vary on what interest rate is legal for personal loans, so check your state's rules if the amount is large. For small personal loans between friends, interest is unusual and often unwelcome.

What if the person says they will pay me back but keeps delaying?

Each time they delay, send a follow-up message that restates the original important date and asks for a new one. After two or three broken promises, stop asking and move to a demand letter. A pattern of broken promises is evidence that the person is not going to pay, and continuing to ask just wastes your time and emotional energy.

Can I take someone to small claims court if I have no written proof, just my word?

It is much harder without written proof, but not impossible. Judges sometimes accept testimony from witnesses or circumstantial evidence like bank statements showing a withdrawal around the time you say you lent the money. However, your case is much stronger with texts, emails, or a note both of you signed. If you have no proof, small claims is a long shot.

What if I lent money to a family member and they refuse to pay?

Family loans are the hardest to collect because the relationship usually matters more than the money. Before you pursue legal action, decide whether you are willing to damage or end the relationship over this debt. If you are, follow the same steps as with anyone else — written demand, then small claims if the amount justifies it. If you are not, you may need to accept the loss or have a difficult conversation about whether this was a gift you were not ready to give.

If I win in small claims court, how do I actually get the money?

Winning a judgment is not the same as getting paid. You have a court order, but the person still has to pay or you have to pursue collection — asking the court to garnish their wages, freeze their bank account, or place a lien on their property. Collection is slow, expensive, and often unsuccessful. Many people with judgments against them straightforward do not pay, and there is little the court will do to force them beyond these collection tools, which require more court filings and fees.