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The question

We have a dear friend with a heart of gold - and a history of impulsive, short-sighted behaviour. After a couple of tough years as a freelance writer, she has decided the solution to her job insecurity is to pay $3,000 to a charity so that she can build houses in South Africa. She's taken to haranguing people on her Facebook page to sponsor her, threatening to "out" anyone who hasn't donated.

When I told her she could be alienating potential donors, she posted this: "I don't need a lecture in psychology. …The money is not for me, I am merely a tool that the donators can use to make a difference. I don't understand why any decent human being wouldn't want to give to charity. SUBJECT CLOSED!"

While I don't doubt my friend wants to do good, I'm worried she's running away from her problems and using the charity as an excuse. Your thoughts?

The answer

Before I mouth off, please bear in mind I don't know the history of your relationship with your "heart of gold" friend; nor have I been exposed to her personal charms.

Perhaps she lights up the room when she enters. Maybe her eyes sparkle with brio, sprezzatura and joie de vivre. Perhaps her bon mots, her eccentric clothes and the insouciance with which she tosses her hair when taking off her bike helmet has everyone in the vicinity, men and women alike, in a state of pinwheel-eyed enchantment.

Because otherwise, based on what you've told me, she just sounds annoying. The type I'd give money to just so she would leave the continent for a while.

I should probably also mention I'm not the most pro-charity person. My wife gets dewy-eyed over televised charity appeals, and seems to donate her time and money to just about anyone who asks.

Me, I'm more the miserly/misanthropic type, with a heart more of stone than gold, muttering darkly as I write the cheques. My feeling is: I've had to pry every dollar I've earned from the tightly clenched fist of the world, in suffering and shame. I'm supposed just to open my wallet and let all the cash be hoovered out whenever I'm asked?

And the people guilt-tripping me for donations always seem to be such ultra-flush, high-flow characters themselves: doyennes, mavens, "ladies who lunch" looking to fill the afternoon hours with worthy activities; fat-cat, haute bourgeois businessmen looking to put a philanthropico-artistic gloss on their stacks of cash.

In your case, of course, it's the opposite. Your friend is flat broke, thus effectively double-guilting you into forking some dough in her direction.

Because not only would your donated dinero be helping put a roof over the heads of needy South Africans, it would also prevent her from having to move into a cardboard box herself any time soon - not to mention giving her self-esteem, motivation, and so forth.

If I were you, though, I would not start tripping on either type of guilt.

I know it's tough when we're talking about a friend who needs help. And no one knows better than me how tough it is to be a "freelance writer."

But I agree it seems like she is running from her problems. From what you've said, I'm not so sure you'd be doing her a favour, in the long run, by slipping her some loot. It's that old charity chestnut: "Give a person a fish, they fish for a day; teach them to fish, they fish for a lifetime." In this case you'd be more giving her a fish than teaching her to fish, I think.

True, she might learn some marketable skills in her South African sojourn and make useful connections. But I think it more likely she winds up right back where she started: broke and "pitching" ideas to editors who get back to her at an incredibly leisurely pace.

Go ahead and give if you want. But based on the aggressiveness of your friend's cash-extraction campaign, it seems unlikely your generosity will leave her awash in gratitude. She'll be more like: "Well, it's about time."

In the end that's my biggest beef: She didn't ask nicely. If someone wants you to give them money without offering any type of goods or service in return, I think they should at least ask nicely.

My advice would be different if she came to you and said: "Listen, it's been a tough couple years, do you think you could spot me some cash until I get on my feet again?" But your friend's attempt to pry open the pocketbooks of her Facebook friends fairly reeks of entitlement.

Bottom line: Unless she is willing to demonstrate a little humility, you should simply not engage. She sounds frustrated with the world. The less you post and point things out, the less her frustration will be focused on you.

One of the beauties of being the one who has the cash, as opposed to the one who wants it, is you can afford not to respond, let alone initiate contact.

So when she utters high-handed iterations like "subject closed," just mildly say "Okay."

And let her sweat it out from there.

Have you created any damage that needs controlling? Send your dilemmas to damage@globeandmail.com.

David Eddie is an author and the co-creator of the TV series The Yard , airing this summer on HBO Canada.

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