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Offensive questions at work: well-intentioned or just plain stupid?

House of Cards fan or not, go ahead and Google the Claire Underwood scene about regretting children. It’s the first true interaction between the First Lady and the Governor's wife—where the latter asks, “Do you regret it, not having children?” Without missing a beat, the First Lady responds with a bit of bitterness, “Do you ever regret having them?”

After watching this House of Cards episode I found myself reliving the day I returned to work after my father's death. I didn’t make it up the staircase before a coworker—one I average three inconsequential conversations with a year—wrangled me into a conversation about the funeral, how my mother was coping, and if I’d been prescribed antidepressants yet. She meant well I’m sure, but it sunk in quickly that the worst part of the day wasn’t going to be the reminder of my father’s passing, it was going to be answering the awkward and inappropriate questions about it.

To ask or not to ask?

We’ve all been there with a bad breakup, death in the family, pregnancy—or just an awkwardly puffy vest—highly personal and sometimes confidential matters that your coworkers can’t help but ask about. But what makes us touch on such inappropriate topics, especially at work? It could be good care and bad manners. Or well-intentioned but poorly executed taste.

In the future, before “comforting” a coworker or asking a juicy question (that's none of your business, pause and ask yourself the following:

[Read also: Emily Post is pissed; enough with the bad manners]

Will asking be helpful? Are you asking because you have a close personal relationship with this person and have touched on this topic before? Then sure, by all means, go ahead. But if it’s simply because you’re aware of the information and are curious, take a step back and reflect on if your probing will be helpful.

How private of a person are they? Sometimes we forget, especially at work, that we are all very different human beings with different preferences and levels of comfort. You may be open about personal matters while a coworker isn’t.

Sometimes we forget, especially at work, that we are all very different human beings with different preferences and levels of comfort.

How close are you to this coworker? Are you in their “inner circle”? Do you chat often and about your personal lives? Have you met outside of work as friends? If not, it's best to send an email of condolences or well wishes, and leave the in-person conversations to their closest confidants. Sometimes in our work lives,

How did you hear this information? Is the gossip mill running and you heard about a private matter through a mutual colleague? Best to leave it alone. And above all, don’t contribute to the rumors.

Is it about you, or about them? Maybe you also had a recent personal struggle and you feel that you have knowledge to share. That doesn’t always mean your well-intentioned advice will be received with open arms. As a recent coworker explained after she lost her mom, hearing about another's loss does not make your own easier. Comparing and assuming your emotions are the same can actually be insulting, so tread carefully.

If you’re still not sure you should say something, but can’t shake the urge, then may I suggest you:

Send a personal email of well wishes before bringing it up in person.

Leave a card on your coworker’s desk to let them know you’re thinking about them at a tough time.

Buy them a cup of coffee away from the office—if they need consoling this is a much more appropriate place to do it.

Make sure you’re alone if you do bring it up in the office. Think of the timing (i.e. don’t get them talking about a nasty break-up or how hard it is to leave their newborn at home, a few minutes before an important meeting).

When it comes to personal matters, it’s best to be cautious and sensitive to your audience. You don't know what emotional triggers exist for other people that don’t exist in your own life. So watch your manners, and keep the offensive questions at work, out of work.

Rebecca Fromm is a Marketing and Events professional in the Bay Area. She's been in the software industry for the better part of a decade, is a wanna-be-writer, lover of books, and a highly amateur yoga practitioner. Find Rebecca on Twitter: @Rebecca_Fromm

Photo by JK Photography.

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