The Do’s and Don’ts of dating your boss – 06 Awkward Complications

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Is Office Romance Still Allowed? - WSJ

Summary of Dating your Boss

  • There are many Risks
  • Need to be strategic- Avoid the Odds
  • Need a careful Plan to make it through

We spend a substantial portion of our lives at work. We generally devote more of our waking hours to work than to home. So it stands to reason that we will form some close bonds.


After all, having a work BFF is essential for getting through the workday in one piece. They are capable of producing even.


But what happens when you begin to sense a deeper connection developing?
Suddenly, you have all these private jokes and the ability to communicate solely through subtle looks. You can finish each other’s sentences and become inseparable at work.


In any case, not yet…

Sure, you’ve considered it. And you know they’re thinking the same thing. But there’s the small matter of them being your boss – ah, nigga.

Dating your boss appears to be a bad idea that should be avoided. But how can you not think about it when you both have such a strong bond and see each other almost every day?!

You may feel alone in this situation or as if you’re insane, but trust us when we say you’re not. In fact, according to a survey, 54 percent of workers have a crush on a coworker or boss.

So, in this circumstance, what will you do?

The short answer is that it is complicated.


So, what’s the biggy?

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According to the same survey, 27% of workers have had a workplace romance, and 27% of these were with their boss or a higher-ranking employee.

Dipping your pen in company ink is clearly not a strange or unlikely scenario. But what’s the tricky part about dating your boss?

There are numerous reasons why you should not date your boss. It’s limitless. Sexual harassment, career risk, emotional stress, job security, relationship conflicts, and so on.

But I’m not here to tell you that you shouldn’t date your boss. I just want to make sure you go into this with your eyes wide open, knowing what to expect and how to prepare.

With that in mind, here are a few major issues to be aware of when dating your boss.


Abuse of Power One of the most difficult aspects of dating at work is the power structure. While a romance may appear to be innocent, when it is between an authority figure and their subordinate, there may be – even unconsciously – abuse of power at work.

We are conditioned to want to obey someone who has direct control over our careers and day-to-day working environments. They can use their power over us to force us into situations we would not otherwise agree to.

Living beings are emotional creatures who crave love and linkage. So, while we may know rationally that dating at work may result in weeping, logic does not have much power over true love.

However, workplace romance should not be entered into lightly. It is possible to be true to your feelings while also being wise, strategic, and sensible. After all, your job and career are on the line.

When faced with the prospect of dating your boss, there is a lot to consider. However, if handled correctly, it can be a win-win situation. Having your soul-mate bestie by your side at work can also help you get through the tough days.

Let’s get down into the nitty-gritty.

The Do’s of Dating Your Boss

The Do's and Don'ts of Dating Your Co-Worker | Inc.com

At first glance, it may appear that there are far more “don’ts” than “do’s” for getting romantic with your boss, but there are things you must plan in advance for.

You don’t want to get your feet wet and get burned. It’s all about being aware of and comprehending the issues, concerns, and implications ahead of time.

With patience and planning, you can reduce the likelihood of negative outcomes while increasing the likelihood of positive outcomes.

1. Do Examine Yourself and Wait It All out

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The consequences of a power differential have already been discussed, and they cannot be overstated. It’s critical that you consider your feelings for your boss and where they come from.

Would you feel the same way if they were your peer or junior? Or someone you met outside of the workplace?

Are you truly attracted to them as a person, or are you attracted to their position and status?

These are critical questions to ask yourself before engaging with a higher-up at work.

Next, in most cases, rushing a decision based solely on emotional knee-jerk responses never ends well. So, don’t dive in right away. Give it some time and see what happens.

2. Ensure That It Is Mutual

In relation to the preceding, once you’ve determined that you’re truly into your boss, the next question is whether they’re truly into you. Remember that all relationships are two-way streets that must be mutual.


If your superior shares your romantic feelings, it has the potential to be something special.


If your boss isn’t interested in dating you, while it will hurt, it will at least provide closure and allow you to move on.
It’s not easy to bring up the subject, but you have to do it at some point to find out if it’s mutual. Otherwise, you’ll just irritate yourself.

3. Be Sceptic.

What happens if things don’t go as planned? This is a question you should seriously consider before entering into a relationship with someone who wields significant power over you.

Sure, they may be all lovey-dovey right now, but once your romance is over, they can turn into an asshole boss.

What kind of situation would that put you in?
Is your workplace policy protecting you and providing you with the necessary support in this situation?
Or is your boss’s power such that if things went wrong, you’d be trapped or stuck in your career?

Would you be able to find a way out?

The answers to these questions may determine whether or not you continue the relationship, or they may lead you to decide that one of you needs to change jobs.

606 Sceptic Stock Photos, Pictures & Royalty-Free Images - iStock

The Don’ts of Dating Your Boss

If, after careful consideration and planning, you’re ready and excited to dive headfirst into the relationship, we congratulate you!

Everyone's favorite alien, fully animated! Get Stitch in both his cute and  grumpy moods in thi… | Stitch drawing, Lilo and stitch characters, Lilo and  stitch quotes

But there are a few things you should never do when dating your boss.

Keeping these things in mind will keep you out of trouble and in good standing with your partner and peers.

1. Don’t Forget About Your Priorities

While love is lovely, it does not pay the bills!

It’s easy to get carried away, especially in a new relationship, but your career should always come first.

In a potential relationship with your boss, you may be putting your career at risk more than they do.
Be cautious, and avoid any actions that could jeopardise your professionalism and put your career in jeopardy.

2. Don’t Be Secretive

While it may be tempting to keep things “under wraps” while you work out your relationship, these things have a way of coming to light.

If the relationship has been revealed, don’t try to keep it hidden because it will create an air of dishonesty, guilt, and shame. Even if you’re not doing anything wrong, secrecy implies that you are. It may even result in severe repercussions from your employer.

So, in this case, honesty is the best policy.

3. Don’t Spread Rumors

The private details of your relationship with your boss-turned-lover should remain just that: private.
Although it’s tempting to either gush and rave or bitch and moan about your “other half” to your work BFF, that’s something you have to avoid when dating your boss.

You want to avoid the gossip trap as much as possible and don’t feed into it. They might be your crush but to everyone else, they’re still a colleague, manager and leader. Nobody needs to hear the good, the bad and the ugly of how they act and behave at home.

Leave all of that shit at home. Don’t bring it up at the office.

Take it easy and wait and see how things pan out.

Take it Easy Bro | Cartoon people, Disney characters, Cute cartoon

It’s true that to dating your boss is a minefield, but if you approach it with caution and forethought, you can make it work. After all, who doesn’t enjoy the thrill of falling head over heels in a new romance? The butterflies, the “good morning” texts, and the excitement of learning new things about each other. You’re floating on cloud nine.

The burden of potentially ruining both of your careers, on the other hand, could have a real dampening effect on this honeymoon phase.

However, if you take all of the necessary precautions, follow the proper procedure, and allow things to develop naturally, you can be free to fall in love without the threat of career suicide hanging over you.

Sure, it’s viable that it won’t work out.

But it could also be the best thing that has ever happened to you.

Aren’t you curious to find out?

Also, if you haven’t read my previous article on the 8 craziest things to do before marriage, what are you waiting for?

Explore Now

I recently read an article about the dos and don’ts of dating your boss. This article inspired me to write about it, so I’ll include a link to that article as well.

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