Dating The Boss, Crossing An Invisible Line?

According to surveys, a quarter of American workers now say they have merrily dipped their pen in the company ink. Fifteen percent say the person they dated was their boss, notes CareerBuilder, a popular job site. Still, data suggests workplace couplings are becoming more unsavory than in the mid-90s, when 20% of heterosexual couples met at work to just over 10% today. The problem is that office romance doesn’t sit well with human resources, especially when you’re hooking up with someone within your chain of command.

Last year, we witnessed the hurried departure of senior leaders at big-name companies like BlackRock and McDonald’s over a consensual workplace relationship. If these firings are any indication, the rules of dating up or down are likely to evolve in the #MeToo era. These changes have been attributed to the rise of the third-wheel in the workplace, i.e. anti-harassment policies. The stronger the prohibition on workplace fraternization, the more likely companies will maintain their retention rate.

Dating Your Boss

It’s not unusual to get lovey-dovey for a like-minded colleague – with the ever-increasing number of hours we spend at work, it’s more than likely to foster feelings for someone from across the cubicle room. This doesn’t mean that issues won’t arise from dating a superior in the workplace. Your colleagues are still going to cluck their tongue, and the HR might make one of you resign from the position.

Dating With Boss

“From an HR standpoint, workplace relationships have the potential to impact employee morale and productivity, retention, as well as the potential for harassment claims that may arise when an overzealous employee attempts to start a relationship with an uninterested party or when an initially consensual relationship comes to an end,” warns Beth Zoller, Legal Editor at XpertHR.

So, if you’re in hot pursuit of a Fifty Shades-eque romance in the workplace, here are a few things to consider.


The boss-employee relationship is not entirely uncommon in the workplace. There’s a good-chance you have caught your boss’s eye, too. According to shocking poll findings by video recruitment website Jobs2View, nearly half of bosses have the hots for a member of the staff. Then again, be prepared for a career brick if things go south. (Similarly, bosses should be vary of the legal ramifications of a relationship with an employee.)

dating your boss and office romance

Everyone will naturally think that the person sleeping with the boss will have the inside scoop on promotions, pay and information, and that undermines trust in leadership, cautions Robert Chestnut, Airbnb’s Chief Ethics Officer.

So, before you embark on the office romance in full swing, it’s important to weigh the risks – and mind you, there are aplenty! First and foremost – there’s a chance the romantic liaison might not end up in happily ever after.

“Think very carefully, up front, and about how you’ll feel if the relationship doesn’t work out,” cautions Robert Chestnut, Airbnb’s Chief Ethics Officer. “If you work closely with the person, be mindful that when a relationship ends, often at least one person will be unhappy, and that can have a big impact on how you feel about coming to work every day.”

There are also multiple possibilities of potential conflicts of interest that can be hard to resolve. Your affair could be fodder for office gossip. Or worse, it could impact your relationship with your work chums. Some colleagues may think the boss is giving you preferential treatment at work.

To avoid claims of dropping the ball, you might actually have to step up your game and work harder than ever.

Everyone will naturally think that the person sleeping with the boss will have the inside scoop on promotions, pay and information, and that undermines trust in leadership, says Chestnut.


Statistics suggest that a boss-employee relationship is more likely to end up in a happy long-term marriage rather than tearful endings and ruined careers. However, this still doesn’t give you a free pass to flaunt your relationship to your colleagues.  “Lunch is fine, but leaving your work station every 15 minutes to chat is not,” cautions Paula Rauenbuehler, an HR veteran and CEO of Executive Leadership Coach. “Anyone who conducts more personal work on company time than is acceptable is at risk of running afoul of company expectations.”

It’s not a bad idea to remove the cobwebs off of the Employee Handbook Manual to read up on the company policies on workplace fraternization.

Consider having rules about how and when you’ll talk about work while off-the-clock. Learn how not to blur professional lines by dredging home issues into the office. PDAs (also known as public displays of affection) are a big no in the workplace. You may no longer hate Mondays but your colleagues will when find the two of you in a smooch galore by the watercooler. Be discreet and don’t indulge in oversharing details of your relationship with other colleagues. Keep your work emails and expense accounts business-oriented. Save private communications for your personal phones and email accounts.

…lunch is fine together, but leaving your work station very 15 min to chat is not.”

Don’t let the relationship consume you, advises Trish McDermott, a founding member of Match and Relationship Coach/Co-founder at Meetopolis. “You will be spending a lot of time together, so make sure you don’t get lost in it. Set boundaries and have a clear understanding of expectations and make sure you are on the same page.”

To avoid claims of dropping the ball, you might actually have to step up your game and work harder than ever. You may find yourself slacking once the novelty of the relationship wears off. Your relationship with the boss should not define your place in the company.


A lot of sexual-harassment companies result from romances gone sour. If workplace fraternization is prohibited in the workplace, your employers may never really know what’s going on until the relationship ends and results in an office squabble. One of you might decide to break it off, while the other wants to relentlessly pursue it and it turns into a non-consensual affair leading to a harassment claim.


What you do when your boss’s conduct is coercive, exploitative and manipulative? You write to the Audit Committee of the Board of Directors, advises Laurie Girand founder and President of I’m With Them, which privately connects victims of work-related sexual misconduct by a common perpetrator.

Individuals that wish to date in the workplace need to remember that dating and office romance is not anything like what you see on TV or in the movies, says Brett Holubeck, Labor and Employment lawyer at Alaniz Law & Associates in Houston, Texas.

“It is not cute when a person keeps asking the same person out over and over again because they believe that they will change their mind. It’s actually kind of creepy,” says Holubeck. “Employees need to understand company policies surrounding workplace dating especially if the romance involves dating between a supervisor and an employee.”

For this reason, some companies require employees to sign a love contract, or a signed statement that you’re in a consensual relationship, which safeguards the company from any legal liabilities regarding unchecked sexual harassment in the workplace.

“It’s a threesome when you are in bed with your boss because your company is involved as well,” says Laurie Girand founder and President of  I’m With Them, which privately connects victims of work-related sexual misconduct by a common perpetrator. “You need to know the company’s policies about romantic relationships. Even if there is no policy, the time has come to speak to HR about the relationship.”

But do what you do when your boss’s conduct is coercive, exploitative and manipulative? “If you find yourself in a relationship in which your boss is using coercion tactics to prevent you from reporting your mutual relationship,” says Girand “it’s time to go straight to the top because your local HR and compliance representatives will be conflicted.”

“If you work at a publicly held company, you’ll want to write to the Audit Committee of the Board of Directors,” she advises.

If everyone at work already knows you’re in a relationship, you might want to get tips and advice from the HR on how to protect your professional reputation. You certainly don’t work your cubicle mates to think you’re being unduly favored; it can plague you with imposter syndrome and hurt your team’s morale. Experts suggest that the people involved in such scenarios should ask to transfer to a new boss or reassign their direct report to another team. This will also help you avoid making a trip to the human resources if the relationship is over.


There’s no reason to mince words when it comes to a boss-employee relationship. What if you both are passionate about your work yet it’s necessary for one of you to leave? If neither of you wants to leave, perhaps it’s best to rethink your relationship. Sometimes operating in different silos may also help if the relationship is going to be long term.

If you’re dating your boss, it is possible you’ll eventually find yourself working with a former partner. How do you deal with an office breakup? We’re adults, but sometimes even the most civilized and mature people are negatively affected by seeing the former partner at work. That’s especially true if you find a new eye candy in your boss’s arms after a fresh breakup. An office romance with the boss is not a bad idea, but it’s something you should consider very carefully as it could have long-term consequences on your careers.

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Priyansha Mistry
Currently editor at The HR Digest Magazine. She helps HR professionals identify issues with their talent management and employment law. | Priyansha tweets at @PriyanshaMistry

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