This post is from Ollie Geiger, a personal finance writer who contributes to MoneyRates.com.

My wife has a friend who likes to talk about how broke she is. This friend – let’s call her “Amber,” since that’s her real name – is fond of complaining about the dire state of her finances each month, even though her income is higher than many of our mutual friends.

But here’s the rub in Amber’s complaints: She is a spender. When she and my wife take shopping trips, she buys some very nice things. We’re talking non-essentials, including lavish gifts for friends and plenty of impulse buys – such as the high-end mountain bike she bought this spring that has since served as a coat rack in her apartment.

Mountain bike/coat rack
Saddest awesome bicycle ever

My wife was fine with not bringing up the obvious to Amber until the irony around the situation began to grow too thick. As my wife put it, listening to Amber complain about money just moments after she showed off her latest purchases was like listening to someone lament their tragic struggle with weight gain as they polished off the last crumbs of a six-foot party sub.

Friends to the rescue?

Eventually, Amber’s complaints over the state of her finances so concerned one of their mutual friends – a friend who makes less than Amber – that she proposed that their group of friends split Amber’s part of the bill for a recent girls-night-out.

“I just couldn’t do it,” my wife later confessed to me. “She thought we’d be doing a great thing for our hard-luck friend, but I knew that all we were doing was enabling her and reinforcing her own bogus story.”

My wife felt bad declining to chip in, but she was now on the brink of telling Amber that she was less a victim of capitalism and more a victim of her own financial obliviousness. Eventually, my wife asked me: Is there any sense in saying anything to her?

I was of two minds. On the one hand, I believe that close friends should be capable of honesty with each other – and Amber and my wife are fairly close. If your friends can’t call you out when we’re doing something foolish, who can? Family may be the answer to that question for some, but critiques from a peer can sometimes ring truer than critiques from your 53-year-old aunt from Jacksonville.

On the other hand, I realize that there’s little sense in criticizing your friend’s behavior if it will only hurt her feelings. Amber can be a bit sensitive, and it’s possible that she might prefer to withdraw slightly from the friendship than change her behavior in the face of a critical comment. If that happened, I couldn’t see an upside to the decision.

I eventually advised my wife to shelve her irritation and move on. If Amber ever directly asked my wife how she could end her financial woes, I’d fully endorse my wife unpacking her true thoughts. But as far as I know, Amber has never done so. It’s possible she even knows the answer to her dilemma, but just likes to vent to her friends about the struggle. I could be wrong, but I wasn’t comfortable recommending anything else under the circumstances.

When is it a good idea to comment on a friend’s spending? How should you do it? Conversely, how would you handle it if someone close to you commented on your spending?

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