We all want to have a healthy relationship with our supervisors – but is it OK to actually be friends with your boss?

Sad as it is to say, buddying up to your boss can make things a little awkward for both of you, and this can lead to unexpected consequences. That doesn’t mean you need to instantly ditch and unfriend your poor manager, but some degree of discretion is advised.

“It does happen all the time – I’ve had my own personal experiences not only being friends with bosses, but also having people who report to me being friends with me,” said Mark Franklin, practice leader at CareerCycles and co-founder of OneLifeTools.

“We can have a good time at lunch having conversations, even having a drink after work or playing hacky sack in the parking lot. I think friendly relations between bosses and employees supports good work and good performance,” he added. “I guess it’s about boundaries and where you set them.”

If you are navigating these tricky waters, try observing these rules for socializing with your superior.

Do: Talk about changing roles and relationships

One of the strangest workplace dynamics is when a close friend and trusted confidante is suddenly promoted to your supervisor.

Your workmate-turned-manager is probably fretting about how to handle this weird social transition too. So, experts recommend the direct approach.

“Help them move into that leadership role by suggesting: ‘I know things will change between the two of us. We’ve been really close, but you’ve got your job with big deliverables and responsibilities, and I know I need to deliver in my role,’” said Joanne Loberg, career consultant and executive coach at JL Careers Inc.

“If a manager isn’t taking the impetus to talk to you about how things have changed, it becomes very awkward. The longer you wait, the more awkward it becomes.”

Don’t: Vent about work issues

One thing should be clear: your supervisor is not a sounding board.

Even if your new boss is an old friend who used to commiserate with you about all your irritating coworkers, your relationship has changed. Your boss isn’t the right target for your workplace whining.

Similarly, if you’re mulling a career change, keep it to yourself. Even if you trust your boss implicitly, you might be putting her or him in the uncomfortable position of weighing your privacy against the company’s needs.

“Be careful how far you let the cat out of the bag with certain sensitive topics that affect your work and performance,” Franklin advised.

Don’t: Accept favourable treatment

The last thing you want is to look like the office suck-up, so if you are hitting it off with the head honcho, be very careful that your new pal isn’t giving you preferential treatment.

“If you’re perceived to have favouritism with that boss, you lose your respect and the ability to collaborate with your colleagues, because they feel that you’ve got one foot up on them,” Loberg said.

Do: Join in on a night out if it feels right

Chances are, any bonding with your boss might happen in off hours, especially if yours is the kind of office where group excursions to the pub are an occasional indulgence.

It could be a good opportunity to blow off steam and get to know your colleagues – and, yes, your supervisor – in a slightly less formal setting.

Don’t: Get wasted

Still, any time a supervisor is nearby, consider that this is the person likely responsible for your performance review. Is this really the best time to test your tolerance?

“If you’re going for drinks after work, know yourself,” Franklin advised. “You know how you behave after a certain number of drinks. So use your better judgment.”

Don’t: Overshare

Close as you might be with a supervisor, some topics are simply not suitable for work.

“When it’s become too close and there’s too much personal information you both find out about – too much about relationships, too much about health issues – it’s not appropriate,” Loberg said.

Don’t: Be touchy-feely

This point can’t be emphasized enough: physical contact at the workplace is almost never acceptable.

“People are very sensitive to how friendly is too friendly. One rule of thumb is keep your body parts to yourself. Don’t touch people,” said Lisa Kay, president and lead consultant at Peak Performance Human Resources Corp.

“Unwelcome touching, regardless of how casual, may not be received that way. Even a friendly tap on the back can be misconstrued by other people. Be aware that you’re in a professional environment; you’re not hanging out in a bar with your friends. So you have to take a different tone and you can’t assume that they’re going to be OK with your level of casualness.”