23 questions you should never ask your boss, even if you're friends

Getting along with your boss can be great, but at the end of the day, it's important to remember that your "buddy" is still your superior, and there's a line you probably shouldn't cross.

Asking the wrong questions can easily set you over the edge.

Aside from the obvious - like anything profane, insulting, or overly personal - here are some questions you should never ask your boss, even if you're friends:

'Um, are you sure about that?'

Your manager doesn't want to hear negativity or a lack of conviction. If you have concerns, state what they are and ask for input.

One of the best approaches in deciding whether to share your thoughts with your buddy boss or ask sensitive questions is to put yourself in their shoes, suggests Lynn Taylor, a national workplace expert and the author of "Tame Your Terrible Office Tyrant: How to Manage Childish Boss Behavior and Thrive in Your Job.'

"Do your comments and questions reflect a positive, can-do, and confident demeanor? Remember loose lips sink ships ­- so choose your words carefully when you feel challenged at work if you want to thrive in your career," she says.

'Did you hear ... ?'

Avoiding gossip and conjecture is a good idea, as it can backfire. Even if you're friends, feeding into the rumor mill makes you look unprofessional.

'Is that really part of my job?'

No job description is ever set in stone. "As cross-functional teams remain the order of the day, you're expected to be flexible and make your boss's life easier," explains Taylor.

"As a side note, the more skill sets you accumulate, the more indispensable you are," she adds.

Saying that you're not willing to go beyond your role shows that you are also not willing to pitch in for the success of the company, says Ryan Kahn, a career coach, founder of The Hired Group, and author of "Hired! The Guide for the Recent Grad."

'Can you ask so-and-so to do it?'

Relying on favoritism is not a good look. And anything that makes other people's jobs harder inevitably makes your boss's job harder, which they'll likely remember the next time promotions are discussed.

'Am I invited?' or 'Why wasn't I invited?'

"This is the grown-up world - not everyone will be invited to everything," says Rosalinda Oropeza Randall, an etiquette and civility expert and the author of "Don't Burp in the Boardroom." "Besides, are you prepared for the answer?"

'Can I leave early today since things are slow?'

It's fine if you have to leave early. But don't say it's because "things are slow" or you have "nothing to do."

"There are always more projects in the pipeline. Bosses want you to show initiative," Taylor says.

'So, what should we do this weekend?'

Making plans outside work with your boss is fine, but you should be discreet about it - certainly never talk about your plans together in front of the entire office. It could make your coworkers jealous and lead to accusations of preferential treatment.

'How do I benefit from this?'

Sometimes your work involves helping others and other departments. Bosses have little tolerance for those who aren't team players, Taylor says.

'Do I have to work with him/her?'

Not playing well with others isn't good in elementary school, nor is it acceptable in the workplace. It's assumed that you are capable of getting beyond personality conflicts in the interest of delivering excellent results, no preferential treatment required.

'Did you make it home OK last night?'

This question is best asked in private or via text message. Coworkers who overhear such a question may jump to some less-than-professional conclusions, like you were out the whole night partying and are probably hungover today.

'You're so thin! What's your secret?'

You may think that you're giving a compliment and asking a innocuous question, but unless your boss has specifically talked about their efforts to lose weight, this topic is a potential minefield. Their secret may be, for example, that they have a serious illness causing them to unintentionally lose weight, which they probably don't want to discuss.

What's more, commenting on someone's physique makes for an awkward conversation.

'Can I borrow some cash?'

Most of us have forgotten to bring cash or our wallet to work once or twice, and, Randall says, in this rare occasion it might be OK to ask your friendly boss to borrow some money for lunch.

"But if your wallet is always in your 'other purse,' don't be surprised if you're excluded from future lunches," she says.

'Why does so-and-so always ... ?'

Whining is annoying, to friends and bosses alike. "If you have a gripe, better to ask how you can attain a certain privilege and leave others out of the discussion," she suggests.

'I'm pretty busy. Can it wait?'

It's your responsibility to ask your boss if priorities have changed, as your objectives must stay aligned with your manager's. "Priorities are rarely stagnant, so as in most cases, your better option is to ask if you should reshuffle them," she recommends.

'See this rash? What do you think it is?'

"Except for maybe your mom or spouse, no one really wants to see or hear about peculiar rashes or any nausea-inducing medical conditions," Randall says. "Limit your sharing to a cold or headache."

'No one will notice if I take a box of the coffee packets home with me, right?'

Believe it or not, pilfering office supplies can be a fireable offense - admitting your crime to your buddy boss is a terrible idea.

You'd better believe that when push comes to shove, they're not going to put their own job on the line to protect yours.

'Are you pregnant?'

This question rarely results in a positive outcome. Either your boss isn't pregnant and you've just offended her, or you've made things awkward because she hasn't chosen to tell anybody yet.

'Can you believe my girlfriend/boyfriend just [did XYZ] again?'

"Intimate details about your personal relationships can divulge unfavorable information about you," Randall says.

Sharing intimate details about your love life falls into the "too much information" category, she says, and "if it doesn't enhance your professional image, or enrich workplace relationships, you should keep it to yourself."

'My breakup has got me all messed up - can I take it easy today?'

Everyone has personal problems every now and then, and turning to friends for emotional support can help - but this should never come at the expense of your professionalism.

"Not to diminish your emotional wounds, but why should your boss's needs be put on hold because you need time to process your breakup?" Randall asks. "This is when you might consider taking a 'sick day' or calling your mom for some love and tenderness."

'What's going on with your lately?' or 'What's your problem?'

You may just be a concerned employee and friend - but if you notice something is off with your manager, there are far better, and more sensitive ways to inquire about the situation.

How you ask or what you say may depend on their specific behavior or what you suspect may be going on - but a couple of good options are: "Hey, by the way ... if you ever need someone to talk to, I'm here!" or, "I just wanted to check in to see if everything is ok."

'Aren't you ready to retire?'

For some people, the subject of age is touchy, and, just like assuming someone's pregnant is a huge no-no, making assumptions and comments about someone's age rarely results in a positive outcome, Randall says.