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Funny Money: How To Collect Money From People Who Owe You

If someone owes you money — a friend, a client, a company — collecting that debt will require you to be persistent and shameless. Although it might be tempting to grab a tire iron and threaten physical violence, these tricks for collecting money owed will help you apply some pressure without landing in prison.

A guide to getting back money from just about anybody who owes you money.Odd how it works — people who owe you money tend to let it slip their mind, but when you owe them, they remember and remind you of it until you finally pay up.

Since you’re financially responsible enough to read this fine site, you surely are the type who makes good on your debts. But not all people are as awesome as we are, and a subset of these unfortunates happens to be the sort who are happy to go on owing people indefinitely, forcing you to figure out a way to get it back from them.

There’s a fine art to fund collection, requiring just the right touch and sense of timing depending on the situation.


Contractors and other work-for-hire types know all too well the feeling of clients who demand your work in a timely manner but don’t reciprocate by paying up quickly. Although being stiffed may feel like a personal insult (cause it is), it’s best to keep feelings out of the matter and stay detached and professional.

Resubmit your invoice every week until it becomes clear that you’re being blatantly ignored. At that point, send them one last request labeled “final invoice” with a note that says you’ll take them to small claims court for the amount you owe unless you hear back within 10 days.

With any luck, you’ll have to follow through with that threat and wind up on a daytime TV judge show.


My favorite trick is to invite the friend to dinner, strategically ordering just enough food to cover the debt, then casually mention when the check comes that, by some crazy coincidence, your portion matches what he owes you for that thing.

If he hems and haws, make it a hard sell by revealing that you’ve forgotten your wallet. You can take this to the next level by actually forgetting your wallet, but he had better bring his unless you want to spend the evening washing dishes.

You can also make a mutual friend, who happens to hold some leverage on the borrower, into a loan shark and sell the deadbeat buddy’s debt to him at a discount. This works particularly well in roommate situations. If the pal owes you $20 that you know he’ll never pay back, have his bills-handling roomie pay you $10 or $15 for the $20 balance, which he’ll tack on to the amount the debt-forgetful amigo owes him for the cable bill.


Everyone warned you not to float the cash for a car down payment to cousin Hank, and they’re all laughing at you because he spent it all on booze just like they said he would.

Maybe he’ll never give it all back to you, but maybe you can work out a payment plan with him, shaking him down for a few bucks at every family function you see him at. Failing that, coax him to work off the debt by doing odd jobs for you or humiliating himself for your amusement. For instance, you can offer to shave $50 off the debt if he shows up at your kid’s birthday party in a Barney costume.

Faceless corporations

Decorum and sensitivity go out the window when you’re dealing with the man. Be loud (meaning firm; don’t yell) and visible (making your calls and emails frequent), and get into the ear of decision makers.

If you struggle to get customer service reps to get you a refund, take to social media or launch an Executive Email Carpet Bomb to get the attention of the powers that be. Always be prepared with receipts and correspondence that serves as evidence of what you’re owed.

Don’t be shy about posting your complaint to the Better Business Bureau, which is the equivalent of an aid at elementary school recess who gets bullies to stop beating up on you.

One last thing

If you don’t like the person who owes you money, you need to watch this scene from A Bronx Tale and apply it to your own situation. If the amount you’re owed is piddling, and serves the purpose of keeping the doofus out of your life for fear you’ll ask for it, just let the debt hang over his head indefinitely and consider it the price you pay not to have to deal with that person.

Published or updated on July 23, 2014

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About Phil Villarreal

Phil Villarreal writes Funny Money weekly for Money Under 30. He lives in Tucson and works for the Arizona Daily Star. He's also an author, blogger and Twitterer.


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  1. Valerie says:

    I have an ex-boyfriend that works for swans that owes me a little over $1000 I have tried to communicate I have been ignored I spoke to his supervisor told him everything and I’m sure he spoke to my former boyfriend I saw the supervisor Who said that he cannot talk about it to me it has been turned over to swans legal department not sure what they can do he is still employed there. I plan on taking him to court next month I am going to argue to the court to either paid me the full amount immediately or face jail or I will seize his car which I paid to get fixed I would love your opinion thank you

    • Valerie says:

      I forgot to mention he is also involved in another court case of not paying back the loan of which he could see jail time over that as well I bonded him out of jail on that that hearing so that’s where The amount came from as well.

  2. Lauren says:

    My boyfriend is currently owed a PAYCHECK from a staffing agency. I’ve never come across this in my entire life. He worked a 50 some hour week with a company, only to be let go due to lack of work, and that was a month and a half ago. No one will talk to him, he can’t get through, and it’s a small agency with about 10 people employed. We know his former company submitted his hours to the agency, but the agency has yet to cut a check. When he calls the agency and actually does get someone, different people tell him different numbers of checks have been cut. Is there anything you suggest in this situation aside from taking them to court? We’re at a loss, and he is in real need of that money.

    • Paul Timmins says:

      Many states have government agencies that handle employment paycheck disputes, labor disputes, and things of that matter. usually having them sniff around is enough to shake the money tree in your general direction.

  3. Brian says:

    I have a cousin who owes me $475 and has failed to pay anything in a year. I have tried to collect on this debt twice and have been stood up both times. The way I look at it is I have 3 options. Wait it out and ask again in a few months. Cut my losses and assume he wont pay back which will probably lead me to not communicate with him anymore. The third option is small claims court which I am trying to avoid because this person is close to me. If it was less than $100 I would care as much. But after a year of not even paying pack a single dollar is quite annoying. What would you suggest in this situation?

  4. Back in my wussier days back four years ago I had a roommate I allowed to stay too long. At the time I was a largely non-confrontal type person so I let it all slide for a year. By the time I finally had enough and gave him the boot he owed me around $3k for rent and his share of heating, electricity and internet. The guy never did pay and is now three quarters the way across the country.

    That experience taught me a nice lesson so I don’t worry about the lost money any more. If he pays ten years from now, awesome. If not, no big deal. All the guilt is on him.

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