3 rude money questions that pay to ask

Breaking the code of propriety can translate to big bucks. (Think Stock Images)Breaking the code of propriety can translate to big bucks. (Think Stock Images)Questions about spending and salary are best kept to oneself. So say arbiters of etiquette at the Emily Post Institute. "Deflect the question with humor," advise the experts at Post's EtiquetteDaily.com. "When asked, 'How much do you make?' respond with, 'My boss thinks he's paying plenty.'"

That may have been proper last century, but in 2010 it pays to break the rules. Fessing up about your salary, your rent or the cost of your designer purse can shed light on financial expectations, insider deals, and cautionary rip-offs. It also grants you access to return the question and reap the benefits.

Sometimes, unspoken rules of privacy are there to protect us. But they can also be instituted to protect those bosses, retailers and landlords looking to profit off our ignorance.

But if you're going to unlock this costly information, you'll need to break the safe like a pro. Proceed with caution, scope out the trustworthy, and weigh the risks of a quid pro quo against the rewards. "A rule of thumb is to share your financial information to the same extent you talk about your lifestyle choices, from dieting to relationships," says Alexa Von Tobel, founder and CEO of the women-oriented financial website LearnVest.com. When it comes down to it, only a few pieces of information are always off limits. "You should never share your social security number, PIN number, or any other sensitive information like that," warns Von Tobel. Aside from that, apply the old adage: it can't hurt to ask. If you're lucky it won't just be painless, it'll pay off.

How much do you make?
It's one of the boldest questions you can ask in our professional culture. But it can be the most rewarding. If you're looking to break into a new industry, salary information from a friend in the field is more useful than any published statistic. You get the benefit of knowing her career trajectory, her responsibilities and the specifics of her employer. While blurring the friendship line with work talk can be daunting, asking a peer to be a mentor will facilitate full disclosure.

But the real high-stakes game of truth or dare is sharing salary specifics with a co-worker. It's awkward, paranoia-inducing and the answer can be hard to stomach. But the benefits can't be underestimated. If you're feeling undervalued at work, finding out about a colleague's salary can serve as hard evidence or surprising consolation. The knowledge can also promote confidence come time for raise and salary negotiations. "With an average inflation rate of 3 percent, you need to make sure that your salary is keeping up with the changing value of the dollar," says Von Tobel, whose site covers salary negotiation tactics. "Not talking about money benefits your boss far more than it benefits you."

But before you embark on an honesty session, cover your bases. Some companies have official rules about discussing salary specifics, while other employer-employee dynamics dictate unspoken guidelines. Breaking them can harm you more than help you if you haven't assessed the situation properly. "Do not do anything that could get you in trouble, so don't break official rules or talk about your salary if you signed a non-disclosure agreement," she says.

If you're in the clear, the next step is scoping out your truth buddy. Von Tobel suggests a trusted friend and ally in the workplace. Ideally, it's someone who is invested in your personal relationship as much as your professional connection. "As long as you don't break any rules, we're not opposed to your conquering the faux pas around money by bringing up the conversation-very tactfully-with a close friend at work," she says.

Explain your concerns and your mutual interests. And when you swap answers, don't freak out. "Money is a sensitive subject, and common social graces would tell us not to talk about salary with coworkers-after all, doing so can make for awkward conversations if you find out that you make a lot more or less than someone with a similar title," warns Von Tobel. "The important thing to remember is that a big difference in salaries is probably not a sign of how much your employer values you; the difference almost always comes down to who was a better negotiator. Treat this as a learning experience and always remember to negotiate for your worth."

How much do you pay for rent?
What's a good deal and what's a rip-off? In renting a home, the answers are hard to find. You can spend months following real estate blogs, checking out listings on Craig's List and talking to realtors in your area. But the real scoop comes from asking friends about their own setup. Most people can relate to the hardships of finding affordable housing, and odds are, if a friend already has their digs lined up, they'll want to help you out too. Just be sure to cover all your bases: Find out if they negotiated their rent, if they paid any upfront cash and if they can recommend a resource for finding a similar deal (ie: their landlord). If they pay a larger amount then you expected, at least you know where you stand with the market.

Just remember, flattery will get you everywhere: if you gush over your friend's home, and suggest that they really scored a find, you're more likely to get a direct answer about the monthly cost. The wariness of sharing information can be more about ego, and fear of being seen as a sucker. But if a person feels safe and respected from the get-go, they'll be more likely to offer up the details.

Asking potential neighbors can be a bit more loaded. You both have a relationship with the landlord and vested interests in your home. If one of you finds out the other has a deal, it can backfire if they complain to the landlord. But you don't have to be so direct. Von Tobel suggests skirting around the direct rent question and requesting an opinion: "Wow, apartment 3B is the same as 4B but the landlord wants to charge me $500 more? What do you think?"

But beware of potential dangers of sharing too much with casual acquaintances. "There's no need to tell people if they are just gathering the information to be voyeuristic," she warns.

How much did your [bag/shoes/outfit] cost?
The fashion world takes offense easily: synthetic fabrics, last season's color, this season's knock-offs. You're not going to win, so why not lose and walk away with a bargain? The thing is, people aren't as offended by this question as we're led to believe.

"As a diehard vintage shopper, I always tell people how much I paid for things," says Lilit Marcus, editor of TheGloss.com. "Some of clothes I love the most and get compliments on are things I got for ten bucks at a thrift shop, and I'm proud of that."

Despite the hierarchical nature of the fashion industry, when it comes to shopping, we are all comrades. Our goal is to find something awesome that we can all afford. Ever wonder who decided it's tacky to disclose items bought on sale? It sure does benefit retailers to make people think buying at full-price is classier than sorting through the bargain bins. "Sharing your own discount finds is a way of undercutting the notion that something is better because you spent more money on it," says Marcus.

All this is well and good amongst friends. But what about a random person at a party wearing the dress you've been coveting? "It can be touchy or even gauche to ask a stranger how much they paid for something," says Leah Chernikoff, an editor at Fashionista.com. "What you want to do instead is approach with a compliment. Say how much you love the look and follow up with a 'where did you get it?'" If you get the sense it was expensive, the response may be hesitant. Expensive purchases go hand in hand with shame and fear of vanity. Chernikoff suggests then, asking in a whisper, "how much?" This doesn't just imply secrecy but a shopper's code of understanding. If they dish, make sure to tell them it was worth every penny.

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