It happens to the best of us — we willingly shoulder a dinner or a group trip booking, or a loved one asks you to help with their bills, and we expect the borrower to pay up when able. No matter the situation's gravity, a debt is a debt. And when you want to collect but are too shy to ask, these tips can help:

1. Put it in writing.
It may seem like a weird proposition to write an agreement down with friends, but doing so helps the borrower understand that you’re not taking the debt lightly (without you having to express that point). For a small amount, it can be as simple as showing them you're keeping track of it via a note-taking app. Otherwise, write down the amount, interest or none, and payment terms. Sign the document and have it notarized if you think that’s what the situation calls for. The document's legality almost ensures payment.

2. Give a clear deadline.
Set a date on when you can expect the payment. You can choose the deadline or have your friend offer you the date. This way, you avoid constantly inquiring about the payment.

3. Go digital.
Let technology do the follow-up for you. For starters, you can make a Google Calendar appointment that’ll send the reminder directly to your friend’s email. TIME also lists a few apps you can try. The ones available locally are Splitwise, Settle Up, and Debtmate. If you’re splitting a bill or sharing for a trip, these apps can help keep track of payments and even send reminders.

4. Be polite.
When the deadline has passed, follow-up politely. Rocket Lawyer says that borrowers are more likely to pay a debt back when asked nicely. Even if it’s a given that you’ve held up your end of the deal and they haven’t, don't be aggressive right away. If you can still afford to wait, you can ask them for another deadline. If you’re open to other forms of settling, bring this up.

5. Know when you have to put your foot down.
In our culture, being upfront about a situation isn’t a norm, and when it comes to utang, showing firmness is almost akin to cutting the relationship off. This is the risk you’ll take, which you should consider because the person who owes you is not fulfilling his word. If he’s clearly showing disrespect for your hard-earned money, set emotions aside and follow-up constantly. If worse comes to worst and there's no other way to go about it, sending a demand letter may be effective.

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