John D. Spooner is an investment adviser, author and novelist. His most recent book is No One Ever Told Us That: Money and Life Lessons for Young Adults. Here, he responds to queries from advice seekers of all ages. Send your conundrums to

My girlfriend asks people what things cost. It’s getting embarrassing. It seems like every time we go out with friends, she has to know what the other couple spent on their vacation or dinner or that new dress. Isn’t it enough to say, “You look nice,” without having to know what everything cost? One of these days she’s going to ask the wrong person, and I think they’re going to put her in her place.

She is a great person in so many ways, but clueless about money matters. She recently asked someone what they paid for their wedding. I cringed. What can I do to wake her up and avoid this pending disaster? I tried telling her that people don’t like to discuss such personal things, but she doesn’t believe me. Sex and money are the two things people are most dishonest about. I know it’s true; I wrote a book with that title, which haunts me wherever I go. Personal questions in the workplace are particularly tricky. These days, in offices, you could be called into the HR police to explain your insensitive questioning. And there are those who see affront in every sentence and facial expression. So you have to be very careful about your conversations in the workplace.

For years, people have asked me about my writing life, things like “Do you ever make any money from that?” Or “How about my free autographed copy?” Or “How many copies did your latest book sell?”

I usually answer them, “Your wife is a dermatologist. What would you think if I asked her what she makes annually?” No one asks people how much money they make, unless they’re clueless or insensitive or rude. Sadly, the average person thinks that people who write or paint or act are not really working for a living. So I never answer the question. But I tell them, “Well, let’s put it this way. I have a seven-figure retirement account.” And leave it at that.

We all know people who care about the cost of everything and the true value of nothing. Like friendship and civility and common sense. Your girlfriend likely wouldn’t want to be mistaken for one of them, so you may have to be a little dramatic. Tell her that it’s rude to ask what people paid for various things. You can say, “Didn’t your parents ever teach you anything?” The strong messages make an impact. Of course, you may have to listen to her complain about her parents. But it all may teach her to wise up.

I’ve recently been elected to the board of the condo association where I live. Already, people are calling, emailing, stopping me in the lobby, complaining about things. I feel like quitting before I’m even officially on the board. How do I play this job, for which I don’t get paid? I’ve felt for a long time that certain organizations—country clubs, condo or co-op boards, gated communities—should be run by benevolent dictatorships, not democracies. Do you remember the Dr. Seuss description of “Tweetle Beetle battles”? Basically, they’re arguments about things that don’t matter much at all, small issues that nonetheless stick in people’s craws and obsess them, to the point that they cannot let it go. You’ll encounter many of these if you stay on your condo board, but you will also learn a lot, particularly about people: the good, the bad and, occasionally, the very ugly.

This can be a real education for you, because condo management is basically a small business, and it can be like graduate school as well. You’ll learn economics, finance, psychology, psychiatry and negotiation, as well as down-and-dirty human nature. You won’t get paid. But it can be a priceless experience.

Just do it. There are term limits; it’s not a lifetime sentence. And you’ll learn a lot about yourself.

My boss caught me looking at LinkedIn on the office computer. How can I convince him I wasn’t job hunting? (I have no problem lying since I was looking at job openings at other companies!) I’d love to see a figure on how many dollars in productivity businesses lose annually to employees shopping online, watching sports, texting friends and family or job hunting. It happens in every office and is almost impossible to police.

The most successful person perhaps ever in Boston advertising had “Burn no bridges” as his premier principle in life. But you’ve now poisoned the well with your boss. He will never look at you quite the same way again, no matter how strongly you protest your innocence.

So good luck on your job hunt. And try to not make the same mistake again. Keep your office computer wanderings to things like and fantasy football.

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