It started so innocently. They were a bit short one night. Maybe it was dinner, maybe it was a cab, maybe it was that third round of drinks that somehow cost $87. “I’ll get you back,” they said, already pocketing their wallet with the confidence of someone who had absolutely no intention of remembering this moment ever again.
That was four months ago.
Since then, you’ve watched them buy new sneakers. You’ve watched them order Uber Eats three times in one week. You saw them post an Instagram story from a rooftop bar last Saturday — the kind of rooftop bar that charges $24 for a glass of wine that tastes like regret. And the whole time, a little voice in the back of your head has been quietly screaming: “WHAT ABOUT MY TWO HUNDRED DOLLARS?”
But you haven’t said anything. Because saying something feels weird. It feels petty. It feels like you’re putting a price tag on the friendship, and what kind of person does that over a couple of hundred bucks?
You do. You do that. Because it’s your money and you want it back. And that’s completely, entirely, one hundred percent reasonable.
Why This Conversation Is So Bloody Awkward
Money between mates occupies this strange cultural no-go zone in Australia. We’ll happily shout a round, split a bill, lend someone cash for a parking meter — but the moment it comes time to ask for money back, we seize up like a laptop with forty browser tabs open.
Part of it is the mateship thing. We’re raised on this idea that good mates don’t keep score, that generosity is a virtue, and that bringing up money makes you tight. There’s an unspoken rule that you’re supposed to just trust that it’ll all even out in the end — and if it doesn’t, well, that’s the price of friendship.
Which is a lovely philosophy until you’re down $300 and your mate is ordering smashed avo at brunch like their bank account isn’t built on your loan.
The truth is, asking for your money back isn’t petty. It’s not tight. It’s not rude. What’s actually rude is borrowing money from someone and then conveniently forgetting about it while they quietly stew about it for months. That’s the breach of the social contract. Not you asking for it back.
Before You Say Anything, Work Out What You Actually Want
This sounds obvious, but hear us out. Before you bring it up, get clear in your own head about what outcome you’re after. Because there’s a big difference between “I want my money back” and “I want my money back and I want them to feel terrible about it.”
If your goal is to get repaid and keep the friendship — which, for most people, it is — then your approach needs to match that. This is a practical conversation, not a trial. You’re not there to prosecute. You’re not there to list every social media post that proved they had money while you didn’t. You’re there to remind them about a debt and sort out a plan to settle it.
If your goal is to get repaid and you don’t care about the friendship — maybe this is a pattern and you’re sick of it — that’s valid too. But know that going in, because it changes how direct you need to be.
And if the amount is small enough that you’d genuinely rather let it go than have the conversation? That’s also a legitimate choice. Sometimes the cost of the awkwardness is higher than the cost of the money. There’s no rule that says you have to chase every dollar. But if you do let it go, actually let it go — don’t silently hold it against them for the next three years while keeping a mental tab. That’s not generosity, that’s a grudge with a running total.
The Casual Approach (For Amounts Under $100)
If we’re talking about a relatively small amount — say $20 to $100 — the best approach is to keep it light and slip it into a natural moment. No formal sit-down required. No serious voice. Just a casual, breezy mention that gives them an easy way to sort it out without anyone feeling like they’re in trouble.
The next time you’re out together, or grabbing a coffee, or splitting something: “Oh hey, do you reckon you could grab this one? I think you still owe me from that dinner the other week.”
Or even simpler: “Hey mate, any chance you could flick me that fifty bucks from the other night? My account’s looking a bit sad this week.”
Adding a self-deprecating reason — “my account’s looking sad,” “I’ve just been hit with a rego bill,” “I’m trying to actually budget for once in my life” — takes the pressure off them and makes it feel like a normal request rather than an accusation. You’re not saying “you owe me and I’m angry.” You’re saying “hey, remember that thing? Cool, let’s sort it.”
Nine times out of ten, this is all it takes. They’ll go “oh crap, sorry, totally forgot” and PayID you before the conversation’s even finished. Most people aren’t deliberately dodging you — they’ve genuinely just forgotten because their brain filed “owe Dave fifty bucks” somewhere between “buy bin bags” and “call the dentist” and it never resurfaced.
The Direct Approach (For Larger Amounts or Repeat Offenders)
If the amount is bigger — say $200 or more — or if the casual approach has already bounced off them like water off a duck’s back, you need to be more direct. Not aggressive. Not confrontational. Just clear.
Pick a private moment. Not in front of the group. Not at a party. Not in a group chat. A one-on-one conversation, either in person or over a call. Text can work too, but only if you’re confident it won’t be misread — tone is hard to convey in a message, and “hey can you pay me back that $300” can read very differently depending on what mood the recipient is in when they open it.
“Hey, I hate to bring this up because it’s awkward, but I lent you $300 a couple of months ago and I do need it back. Is that something you can sort out this week?”
Notice what that sentence does. It acknowledges the awkwardness (so they don’t feel ambushed), it states the amount clearly (so there’s no room for “I thought it was less”), and it gives a timeframe (so “I’ll get you back” doesn’t become another four months of nothing).
If they can’t pay it all at once, that’s fine — suggest a plan. “No worries if you can’t do it all in one go. Could you do $100 this week and the rest over the next couple of weeks?” Most people respond well to this because it shows you’re being reasonable while still making it clear that you actually expect to be paid.
The “I’ve Already Asked and They’re Still Dodging Me” Approach
Right. So you’ve asked. Casually. Then directly. And somehow the money still hasn’t appeared. The excuses are getting more creative. “I’ll transfer it tonight” — nothing. “Oh my banking app is playing up” — convenient. “I get paid on Friday” — Friday comes and goes like a ghost.
At this point, you’re dealing with one of two things: either they genuinely can’t afford to pay you back and they’re too embarrassed to say so, or they’re hoping that if they stall long enough you’ll eventually just drop it.
For the first scenario, a bit of empathy goes a long way. “Look, I’m not trying to make this harder than it needs to be. If money’s tight right now, just tell me and we can work something out. I’d rather know where things stand than keep chasing it.”
That gives them an out to be honest without losing face. And if they are genuinely struggling, you can agree on a realistic timeline — even if that means getting paid back $20 a week over the next few months. Slow money is better than no money, and it keeps the friendship intact.
For the second scenario — the deliberate dodger — you need to be firmer. “Mate, I’ve asked about this a few times now and I really do need it sorted. Can you transfer it today?” No softeners, no escape routes, no “whenever you get a chance.” Today. The specificity matters.
If even that doesn’t work, you’ve got a decision to make about how much the friendship is worth versus how much the money is worth. But at the very least, you now know something important about this person’s character — and that information is valuable even if the cash never shows up.
The Group Situation (Splitting Bills, Group Trips, and Shared Tabs)
Individual debts are one thing. Group money situations are a whole different circle of hell.
You organised the Airbnb for the group trip and everyone was supposed to pay you back their share. Three people have. Two people haven’t. One person has “forgotten” despite being in the group chat where you posted your bank details four separate times with increasingly passive-aggressive captions.
Group debts are harder to chase because there’s a weird dynamic at play — nobody wants to be the person who makes the group chat awkward by bringing up money. It feels like you’re punishing the whole class because two people didn’t hand in their homework.
Here’s what works: don’t chase individuals in the group chat. Send private messages. “Hey, just sorting out the final payments for the Airbnb — your share was $180. Could you flick it through when you get a chance?” It’s polite, it’s specific, and it doesn’t put them on blast in front of everyone.
For future reference, apps like Splitwise are genuinely useful for group expenses. They track who owes what, send reminders automatically, and take you out of the uncomfortable role of being the group’s debt collector. Use them. Your friendships will thank you.
And here’s a golden rule for group trips and events: collect money upfront wherever possible. “I’ll book the house but I need everyone’s share before I pay” eliminates the problem entirely. Yes, it feels a bit transactional. But it’s a lot less transactional than chasing five people for money for the next six months while slowly resenting every single one of them.
What Not to Do
A few approaches that seem tempting but will absolutely make things worse:
Don’t bring it up when you’re angry or drunk. “You know what, you still owe me three hundred bucks” delivered at midnight after four schooners is not the calm, mature conversation you’re imagining. It’s the start of an argument that’ll be screenshot and sent to four different group chats by morning.
Don’t involve other mates. Going to mutual friends to complain about the debt — or worse, asking them to bring it up on your behalf — turns a private matter into group drama. It makes the person feel ganged up on, and now instead of one awkward friendship you’ve got five.
Don’t use social media. A vague tweet about “people who borrow money and conveniently forget lol” is not as subtle as you think it is. They’ll know it’s about them. Everyone will know it’s about them. And now you look petty while they get to play the victim.
Don’t keep a visible running tab. “That’s okay, I’ll add it to the list” said with a tight smile after they fail to shout a round is not the power move you think it is. It just makes every future interaction feel like a transaction.
Don’t lend them more money. This one sounds obvious but you’d be staggered how often it happens. “I know they still owe me $200 but they really needed help with…” No. The first debt gets sorted before any new lending happens. You’re a mate, not a bank. And even banks have lending criteria.
How to Stop This Happening Again
Once you’ve been burned by a mate-debt situation, you tend to develop a pretty solid policy for the future. Here are the rules that most people land on after going through this once:
Never lend more than you can afford to lose. This is the big one. Before you hand over any cash, assume you might never see it again. If that amount would genuinely hurt you financially, don’t lend it. Suggest other ways to help instead.
Set expectations at the time of lending. “Yeah no worries, can you get it back to me by next Friday?” is so much easier to say in the moment than it is to bring up three months later. A casual agreement at the point of lending saves an awkward conversation down the track.
Use payment apps immediately. If you’re splitting a bill or covering someone’s share, get them to PayID or bank transfer you on the spot. “Just flick it through now while we’re thinking about it” is perfectly normal and eliminates the forgetting problem entirely.
Know your repeat offenders. Everyone’s got one mate who’s perpetually broke, perpetually borrowing, and perpetually “getting you back next week.” You love them. They’re great fun. But they are not getting another cent until the current tab is cleared. Boundaries aren’t mean — they’re self-preservation.
The Bottom Line
Asking a mate to pay you back is uncomfortable. There’s no way around it. Money makes things weird, and no amount of “it’s fine, don’t worry about it” actually makes it fine when you’re quietly fuming every time they tap their card on something frivolous.
But here’s the thing — a friendship that can’t survive a polite request to settle a debt isn’t much of a friendship. Good mates pay each other back. Good mates don’t make you feel guilty for asking. And good mates definitely don’t buy a new pair of Nikes while pretending they forgot about the $200 they owe you.
Keep it calm. Keep it kind. Keep it direct. And next time? Get the PayID transfer before the second round.
