Money confessions – Frugal friends

Money messes, meet real talk — straight-up advice on your biggest financial dilemmas

This week's money confession:

I've known my childhood best friend for over 25 years. We were best friends right through school and our friend group is still close. I love her like family. But my big gripe is: she's a massive cheapskate.

She grew up without much money at all and had a rough upbringing, so I try to cut her some slack. Still, her habits are really starting to bug me. She often "forgets" her wallet and says she'll pay me back, but never does. She's always the last to pay when we have a group dinner and often doesn't pay more than a few bucks, because everyone else has rounded up. If I buy her concert tickets for $80, she'll buy my $20 dinner and 'call it even'.

The final straw was our girls' weekend this Easter. Everyone had a different task – some bought the drinks, others paid for petrol for the drive, and she and I were to go halves on the groceries. We filled up a trolley together and I paid, and she still owes me $120. It's not a huge amount, but it's the final straw. I've asked for the money back 3 times and she keeps brushing me off.

I don't like confrontation and I don't want to impact our friendship – but I can't afford to keep being her friend! What should I do?

Sarah Megginson, Head of Editorial at Finder, says:

There's a couple of things to deal with here: what's happened in the past, and what's going to happen in the future.

A dynamic has been set and you've ended up stuck in a rut with your friend, where she now expects you're going to pay the bill or cover her share. She may not even intend to turn up without her wallet or short of cash – but you keep bailing her out and enabling the behavior, and she keeps taking advantage. I'm not suggesting you're responsible for her poor choices at all; moreso pointing out that you're a willing participant, so you have the ability to change this dynamic.

It sounds like she's important to you and you don't want to throw away such a long friendship over this, so you have to make a decision about all that money spent so far. Do you want to tally it up and ask for it all back? Are you happy enough to get the grocery money back? Or would you be okay with the idea of leaving all of that in the past and starting fresh?

There's no right or wrong and you should try your best to park any resentment, and focus on the boundary you're trying to create for the future. You might feel that recouping that money is important for accountability, and that you can't move forward without hashing it out with her. Or you might decide, for your own peace of mind, that you're okay with letting bygones be bygones and you'll leave it all in the past, but you want to set a clear new boundary going forward.

From there, you have a chance to set a new boundary and you don't have to be rude, mean or confrontational about it. Just stick to the facts and keep it simple and straightforward. When they invite you to do something, say: "That sounds great, I'm keen! But I've paid for you so often in the past and you haven't repaid me, even when reminded. Shall we grab a coffee and go for a walk instead?"

This way you haven't said no and you've kept the door open for your friendship. But you've also stopped enabling the stingy behaviour by establishing a clear boundary that shows you're no longer willing to foot the bill. Depending on their reaction and how that next catch-up goes, you can decide where to go from there.

Does OP need to have a straight-up chat with her friend?