• There are many risks associated with dating your boss
  • Be strategic in your decision making to avoid potential disaster and up the odds of success
  • You can make it work through careful planning
We spend a huge proportion of our lives at work. We typically spend more of our waking hours at work than we do at home. So it makes sense that we’ll build some close relationships.

After all, having a work BFF is a must to get through the working day in one piece. They can make even

But what happens when you start to feel a deeper connection blossoming?

Suddenly, you’ve got all these private jokes and the ability to communicate with subtle looks alone. You can finish each other’s sentences and you become inseparable in the office.

People even start to ask you if anything is going on. But there isn’t.

Not yet anyway…

Sure, you’ve thought about it. And you know they feel the same way. But there’s the tiny detail of them being your boss - ah, shit.

We’ve all heard the horror stories.

The poor girl who dated her boss, and then mysteriously disappeared as soon as the relationship was over.

The junior guy who did a terrible job of keeping his relationship with his lady boss a secret, only to end up in litigation.

You know that these are extreme examples - but what if the worst happens?

Dating your boss seems like a terrible idea, one best steered clear of. But how can you avoid thinking about it when the both of you have such a connection and you see them literally every day?!

You might feel alone in this situation or like you’re being crazy, but trust us, you’re not. In fact, this survey from the Society for Human Resource Management showed that 54% of American workers had a crush on their co-worker or boss.

So what should you do in this situation?

The short answer - it’s complicated.

What’s the Big Deal, Anyway?

The same survey mentioned above found that 27% of American workers have had a workplace romance and 27% of these were with their boss or higher up.

So clearly, dipping your pen in company ink isn’t a strange or unlikely scenario. But why the big taboo on dating your boss?

There are so many reasons against dating your boss. It’s endless. Everything from sexual harassment, career risk, emotional stress, job security, relationship conflicts etc.

But we’re not here to tell you not to date your boss. We just want to make sure you’re going into this with eyes wide open and knowing what to expect and how to prepare for it.

With that noted, here are a few of the big concerns about dating your boss that you should be aware of.

Abuse of Power

A big challenge with dating at work is the power structure. While a romance might seem innocent, when it is between a figure of authority and their subordinate, there may be - even unconsciously - abuse of power at play.

When someone is directly in control of our careers and our day-to-day working environment, we are conditioned to want to obey them. They can manipulate this authority over us by coercing us into situations that we otherwise wouldn’t agree to.

The sticky point here is that, at times, the victim of this kind of manipulation may not even be aware that they are being manipulated. They may find themselves forced into a romantic or sexual relationship with their superior - but be fully convinced that it is consensual and of their own free will.

On the flip side, those in a position of power can be blind to how that power holds influence and control over their subordinates’ actions.

This study from Cornell University found that suitors grossly underestimate how hard it is for their love interest to reject their advances. So, they keep on pursuing because they’re not getting any push back.

And when combined with this study from Kellogg School of Management, it shows that power has an inverse relationship with empathy and increases the likelihood of abuse of power in a workplace romance.

These blurred lines are exactly why intimate relationships between leaders and their subordinates are discouraged and, in some workplace, totally banned.

Conflict of Interest/Favoritism

If a relationship between a manager and a member of their team does go ahead, there will definitely be a change in the team dynamic.

We naturally favor those we have close bonds with, and in a work environment this could look like favoritism in the form of receiving better and/or easier assignments, getting more positive feedback, more pay raises and/or promotions, or not being reprimanded for poor performance.

And don’t think that coworkers won’t notice this or find out about the relationship. They will. There’s no avoiding the gossip trap.

Nobody wants to work in a team where they feel that someone else is being treated preferentially - especially when it’s as a result of a romantic relationship.

This kind of behavior could lead to low team morale, resentment among co-workers, underdevelopment of key talent within the team and even resignations. Plus, it makes navigating office politics even harder than normal.

It’s important to note that some of these challenges could happen even when the boss has made sure not to engage in favoritism. If the relationship is public knowledge, then even the perception of favoritism can have a negative impact on the team.

When It Goes Horribly Wrong

You might be called somewhat pessimistic for thinking about the end of a relationship before it’s even begun - but in a workplace setting, this is a must.

You gotta think this through.

The ramifications of a breakup when that breakup is with your boss are far-reaching, affecting your personal life and your professional life.

Sexual harassment and retaliation may occur, especially if the subordinate ended the relationship. One partner may continue to pursue the other in the office, or place unwanted attention on them in a quest to win them back.

It can get real fucking messy.

Even in the case of an amicable breakup, the boss may subconsciously punish their ex-partner through withholding opportunities, being overly harsh or critical or being generally less supportive.

Whatever the circumstances of the breakup, a difficult work environment for at least some time after the event is inevitable.

The consequences of a breakup with your boss can even affect your long-term career. They may influence the opinion of others in the business and stunt your opportunities. They could totally screw you over in your annual review or write a bad reference for you if or when you eventually decide to move on.

In short, breakups suck - but a breakup that involves your boss can really really suck.

Despite all of these concerns, office romances can and do work. This CareerBuilder survey of over 800 full-time employees in the US found that 31% of co-workers surveyed who started dating at work ended up married.

So what are the do’s and don’ts of getting jiggy with your boss?

How To Date Your Boss

Humans are emotional beings, and we long for love and connection. So while we might know logically that dating at work could end in tears, logic doesn’t wield all that much power over true love.

That said, workplace romance isn’t something to jump into blindly. It is possible to be true to your feelings while also being smart, strategic and sensible at the same time. After all, your job and career is at stake.

There’s a lot to think about when facing the prospect of dating your boss. But, if handled well, it can be a win-win situation. And, having your soul-mate bestie by your side at the office can help you get through the rough days at work.

Let’s get into the nitty-gritty.

The Do’s Of Dating Your Boss

At first, it may seem like there would be far more “dont’s” than “do’s” for getting romantic with your manager, but there are things you need to plan and prepare for.

You don’t want to jump into this and get burned. This is all about knowing and understanding the issues, concerns and implications beforehand.

With patience and planning, you’ll minimize the chances of any bad things happening and improving the odds of something good coming out of this.

1. Do Check Yourself & Wait It Out

The implications of a power imbalance were discussed earlier, and these really cannot be overstated. It’s important you reflect on your feelings for your boss and where they stem from.

Would you still feel this way if they were your peer or your junior? Or someone you met outside of work?

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

These are important questions to ask yourself before getting involved with a higher-up at work.

Next, in most cases, rushing a decision that is purely based on emotional knee-jerk reactions never ends up going well. So, don’t dive into this right away. Give it a few months and see how things shake out in terms of your emotions.

Wait it out.

2. Do Ensure That It’s Mutual

Related to the above, once you’ve concluded that you really are into your boss, the next question is, are they truly into you. Remember, all relationships are two-way streets and it’s gotta be mutual.

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

If your boss doesn’t have any interest in dating you, while that will sting, it will at least provide closure and you can move on.

It’s not easy to bring up the subject, but at some point, you’ve gotta do it so you can find out if it’s mutual. Otherwise, you’ll just drive yourself nuts.

3. Do Know Your Workplace Policy

Once it has been established that the feelings are mutual and from a healthy place, it’s important to know exactly what kind of situation you guys are getting into.

While there is no law against hierarchical workplace relationships, each company will have a specific policy relating to it.

Be clear on the rules before you get into anything - you don’t want to be hit with any unwelcome surprises.

Most companies will require you to disclose your relationship and some will require changes in reporting structures. This might require one of you to move to another group or department.

It’s imperative that you know what will be expected of you before you get involved with your boss, and decide what compromises you’re okay with.

4. Do Assess The Risk & Reward

This might not be sexy or romantic but neither is finding yourself ostracized from your work community or stuck in a role that is beneath you.

This study from the Australian National University found that the subordinates in a hierarchical workplace romance were less likely than their counterparts not in relationships to be promoted or selected for training opportunities by third parties.

Fewer opportunities, the potential damaging of relationships with colleagues and even the question of whether your job promotions are because of your work achievements or your bedroom skills - all of these are risks you take when entering into a relationship with your manager.

The question is, whether the potential rewards are worth it.

5. Do Be Pessimistic

What will happen if things don’t work out?

This is a question you’ll need to seriously think about before jumping into a relationship with someone who holds considerable power over you.

Sure, they might be all lovey-dovey now but they can turn into an asshole boss the moment your romance ends.

What kind of position would that leave you in?

Does your workplace policy protect you and offer the necessary support in this situation?

Or is your boss’s influence such that, if things did go south, you’d be trapped or stuck in your career?

Would you have a way out?

The answers to these questions may determine whether you go ahead with the relationship or not, or may lead you to decide that one of you needs a change of workplace.

6. Do Be Honest and Open

If a workplace romance is going to succeed, it’s important you are open and honest both with each other and with your employer.

Discuss at length the implications of your relationship, what risks you are willing to take and how you will support each other. The more you guys talk about this, the better.

Without being clear on this, you may find yourself in a position where you’re suddenly expected to change roles or leave the company in order for your relationship to progress. 

7. Do Keep Healthy Boundaries

Just because your colleagues will know you’re in a relationship with your boss, doesn’t mean they should be able to see that you two are head over heels for each other.

When in the office, your relationship should be as professional as possible. There should be no PDAs, no flirty eyes across the meeting room and no discussion of date night in the open-plan office.

Not only is this important for the two of you to remain effective in your roles, but it is also key that you don’t create an uncomfortable working environment for your colleagues.

Third wheeling is a drag at the best of times - imagine having to endure it at work!

The Don’ts Of Dating Your Boss

If, after deep consideration and planning, you’re ready and excited to jump feet first into the relationship, we’re happy for you!

But we do need to remind you of a few absolute don’ts for dating your boss.

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

1. Don’t Forget Your Priorities

While love is beautiful, it doesn’t pay the bills!

Especially with a new relationship, it’s easy to get carried away - but your career should ultimately come first.

In a potential relationship with your boss, you may also be putting more at stake in terms of your career than they are.

Be smart, and don’t make any moves that could see your professional credibility ruined and your career in the dump.

2. Don’t Be Secretive

While the temptation might be to keep things on the “down low” while you figure your relationship out, these things have a way of coming to light.

If the relationship is outed, don’t try to keep it a secret because it creates an air of dishonesty, guilt and shame. Secrecy implies that you’re doing something wrong, even if you aren’t. It can even lead to harsh consequences from your employer.

So, honesty really is the best policy in this scenario.

3. Don’t Bring Work Home

When in an office romance, setting solid boundaries between work life and home life can be difficult, but if you don’t, it can be a huge burden on the relationship.

Especially when dating your boss, there needs to be the ability to work at work, without it affecting your personal relationship.

From giving bad feedback to setting tight deadlines, there are a ton of actions that your boss / lover could take at work that you might take personally or want to bring up at home.

Don’t do that.

You must disconnect from work and leave all bullshit behind. Treat work life and home life as separate worlds. So, you gotta constantly remind yourself - at work, they are your manager and nothing else.

4. Don’t Abuse Your Relationship

Related to the above point, it might be tempting to try and gain extra perks from banging the boss.

This is a definite no-no.

Firstly, you’ll put your partner in an awkward position by attempting to get them to treat you favorably over others. This could get them into huge trouble and conflict with their ethics.

Secondly, you’ll drive a wedge between yourself and your other teammates. Not such a smart idea if you want happiness to happen more often at work.

This also applies to slacking, cyberloafing or becoming less effective at work. Your personal relationship with your manager isn’t an excuse to take your foot off the pedal. If anything, it’s quite the opposite as you don’t want to attract criticism from others in the company.

5. Don’t Gossip

The private details of your relationship with your manager-slash-lover should stay exactly 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.

6. Don’t Abuse Company Expenses

One of the perks of dating a senior manager is that you can dine out on the company dime right?


This is very dangerous territory and something to be carefully avoided. Even just one drink paid for with company expenses can attract a huge amount of suspicion and get you both in a shit load of trouble.

In some cases, these misuse of company funds triggers internal investigations and the both employees may have to prepare for job loss.

Even if your boo suggests it, be sure to quickly and firmly shut them down. You don’t want to get your asses fired.

7. Don’t Date Married Men/Women

All of the potential risks of dating your boss are amplified if that person also happens to be married. It turns a complex situation into mission impossible with little chance for survival.

Even if they are in the process of separating or getting a divorce, stay on the sidelines and wait it out until they are truly single. You don’t know what’s happening behind the scenes and you definitely don’t want to be involved in any of that bullshit.

Dating married colleagues is messy as fuck and will attract all kinds of office drama that could kill your personal brand and haunt you in your career.

If you want an easy life, just don’t do it!

Take It Easy & See How Things Work Out

It’s true, dating your boss really is a minefield - but if you approach it with some caution and a lot of forward-planning, you can make it work.

After all, who doesn’t love the excitement of being caught up in a new romance?

The butterflies, the “good morning” texts and the joy of finding out new things about each other. You feel like you’re on cloud nine.

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

But if you take all the right precautions, follow the right process and let things develop naturally, you can be free to fall in love without the shadow of career suicide hanging over you.

Sure, it might not work out.

But, it also might be the best thing that ever happened to you.

Aren’t you excited to find out?

Feel Better,

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