Money in a glass

I'll Pay it Back, I promise

October 05, 2026•6 min read

"I'll Give You the Money Back Next Week" and Other Things That Never Happen

"I'll get it all back to you in a week or two." They're still waiting.

"Can you stop and buy me a coke on the way home? I'll give you the money when you get here." They never get the money.

"Your sister is struggling at the moment. Can you lend her some money? I promise she'll give it back." She never sees that money again.

Does any of this sound familiar?

Have you been hit up by family and friends, made to feel guilty until you helped them out, and then become the worst person in the world when you asked for your money back?

An alarming number of women tell me stories like this. For some it's a small amount here and there. For others it's a large sum. Most never see the money again, and if they do, it's only a fraction of what they're owed.

So why do we lend money when there's a good chance we won't get it back?

Because humans are caring, and we want to help. There's also often an underlying belief that if we don't help, they won't love us anymore. Then there's the guilt, because we have dollars and they don't.

Plenty of us also grew up hearing, "Oh, your poor sister, she has nothing. Couldn't you help her out?" Now you're stuck saying no to your mother, which comes with a whole other set of beliefs.

Newsflash. Anyone who stops loving you because you didn't give them money never loved you in the first place.

One of my first serious boyfriends borrowed $5,000 from me to buy a car. I didn't hesitate. I was young, extremely trusting and thought he loved me. At first he paid a bit back each week, then every two or three weeks. Then the excuses started, and they got bigger and bigger until the payments stopped altogether.

We broke up before I got the rest of it back. Should I have stayed until I did? Hell no. You don't stay in a relationship because someone owes you money.

So how do you say no without feeling like the worst person in the world? Here are three things to try.

1. Get in first

Don't give them the chance to ask. When they start telling you about their money troubles, respond with something like, "Gee, that sounds like a tough situation. I hope you get it sorted." Then change the subject.

2. Say it plainly

If they do ask, keep it simple. "I'm unable to lend you any money."

Their financial needs are not more important than yours, regardless of what you're spending your money on. I've seen women go without because they bought their partner smokes and grog on demand. I've seen women left embarrassed after lending money to a partner, only to find him at the pokies.

It's not really about the money. It's about having the confidence to set boundaries with the people you love and to hold them when someone tries to walk straight through. I know, it's easier said than done. But if we don't start, nothing changes.

3. Hold the line when the guilt card comes out

The first no is the hardest, especially with someone you love. It will take all your courage. This is your Hurdle in Tight Jeans moment, and it won't feel comfortable.

They might ask why. They might try to make you feel guilty. They might get angry, or play the "I'm so disappointed you can't help your sister" card. Here's what's worth remembering. They can't see what lending this money costs you, or what it does to your relationship with them. All they see is a no. That doesn't make you the bad guy.

So when the pushback comes, say no again. Don't explain, don't negotiate and don't apologise.

Look them in the eye and say, "I won't be lending you any money."

If they keep going, offer what you can genuinely give. "I'm happy to support you in other ways, like being someone to talk to, but I'm not lending you any money."

If Mum is asking on your sister's behalf, try, "Mum, my sister is an adult. It's time she put her big girl pants on and worked this one out herself."

Then watch your voice. Keep it steady, and don't let the pitch climb or the volume rise. A higher pitch tells them you're nervous, and anyone good at manipulation will see that as an in. Say it slowly, breathe, and let the silence sit there (it feels like an hour, it's actually about four seconds).

The "just until payday" crowd

These are often harder to deal with than the big asks, because it's a little bit here and a little bit there. They're also the most likely to get angry.

You know the ones. They let you pay for everything, then disappear when it's their turn. They give you a bullshit excuse about where the money went, or tell you it's none of your business.

With these people you'll need to say no again and again. Have a line ready for when you're out together, like "I've only got enough for my meal." Leave out words like "sorry" and "not at the moment", because they invite another go.

You also need to be prepared to walk away from the relationship. I know that's confronting. Sometimes the hardest choice is still the right choice.

What happened when I held the line

Remember my boyfriend and the $5,000?

When I stopped accepting the excuses and asked for the rest of my money, he lost interest in me. Pretty much overnight.

That told me everything. The money was never really about the car. It was the start of him having control over me, and I could see exactly where that road led.

So I walked away. I never saw the rest of that money, and I'd make the same call tomorrow.

That was my Loosen the Top Button moment. Holding the line didn't leave me worse off. It showed me who he really was, and it showed me I could do a hard thing and still be standing.

That's how confidence gets built, through action, not by waiting until you feel ready. Each time you hold the line, you collect a bit more evidence that you can. Nobody is coming to do this for you.

You already have everything you need. The strength, the smarts, the ability to do hard things. You just need to be willing to shake in your boots while you do it.

Have you been the one handing over the cash and carrying the guilt? Send me a message at [email protected] if you need someone in your corner.

Yes, I just quoted Dirty Dancing in a blog about money, and I stand by it. No one puts baby in the corner.

Kylie Kerr
Engineering leader turned confidence coach, change navigator and founder of The Big Girl Pants Movement.
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