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I have a friend who’s been unemployed on and off the past three years. Recently, she lost her job again. I’ve tried being as supportive as possible but even when she was fully employed, she was living beyond her means – and still is, mainly at the expense of her two friends (I’m one). Many people including her two friends have tried warning her, but to no avail. The situation has become a burden not just financially, but emotionally and physically. I care about her deeply, but I’m reaching a point where I can’t really handle the situation any more, and I feel like I’m being a terrible nag around her.

There were a few things I didn’t understand about your question.

Like why do you sometimes refer to yourself in the third person (as in “her two friends”)?

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I don’t know what that means, exactly, but can’t imagine that’s a good sign. If I’m complaining about a friend and I suddenly switch to the third person – e.g. “Fred’s killing me! Dave doesn’t know if he can take it any more” – you can guess I’m probably already starting to moonwalk away, mentally, from the guy.

But let’s talk about thrift. Sounds like you’re lending your friend money on a continuing basis. Big mistake. I don’t mean to sound too Jane Austen-y here, but it seems almost axiomatic to me, a universal aspect of human nature, that when we lend money, we want the recipient to be careful in the spending of it.

It’d kill me, for example, to lend money to a friend who was crying the blues financially (“I just don’t know how I’m gonna make ends meet, Dave!”), then pass the patio of a ritzy restaurant only to spot him or her waving the waiter over:

“I’ll have the bay scallops followed by the lobster.”

“Excellent choices, sir.”

“Do you think the Montrachet would pair well?”

I’m a Scrooge by nature – I can barely stand to watch my money being spent by me. To watch someone else splash my money around? It would gnaw like a fox at my innards; it would bend my mind into a pretzel.

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What I’m trying to say is: Stop lending your friend money. Be supportive of her emotionally, spiritually – just not financially.

I believe that turning off the cash-flow tap to your friend will have a two-pronged effect: First, it’ll release you mentally and emotionally from the gut-churning hamster-wheel of monitoring her spending habits. Second, it’ll help send the message that now, perhaps, it is time for her to get up on wobbly legs and stand on her own, financially.

Lord knows, it can be hard. I’ve always thought of it as a full-on battle, bullets pinging off my helmet, metaphorical (thank God) mustard gas rolling toward my foxhole as I attempt to storm the ramparts of a mocking, largely indifferent, shame-dispensing world.

It’s a melee out there, a brawl, a no-rules knife-fight: anyway, so it’s always seemed to me. That’s my weltanschauung, for better or worse.

These days, with a pandemic gripping the globe by the throat, more so than ever.

Convince your friend the time for flitting around, borrowing from friends and complaining over chardonnay is over, at least temporarily. That these are what the Bible calls “childish things”: time to set them aside in favour of a steely determination vis-à-vis career, life and the future.

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It won’t happen overnight, of course. But if “her two friends” can be patient (and you’ll be surprised, I predict, how much more patient and even-keeled you’ll be once you stop lending her money), you can get there eventually, incrementally.

Meanwhile, maybe share some of your thoughts and tips on the gentle art of thrift.

You’ll be doing her a massive favour. Thrift is a lost art, I believe. Our great-grandparents would be aghast and awash in disbelief at our spending habits.

And it’s one I have a funny feeling we may all need to relearn in the days ahead.

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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