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12 Tips to Keep in Mind When You Date Your Boss

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If you’re dating your boss or are in love with them, keep these 12 tips in mind if you don’t want your relationship to interfere with your work life. By Sophia Strutt

dating your boss

It’s hard to resist a boss’s charm.

And it’s harder when you’re constantly interacting with them and getting attracted at the same time!

It’s true, people fall in love all the time.

And it can happen at work too.

And sometimes, you may find yourself falling for your boss or dating them even before you realize it.

Of course, you get to spend all day working in the same office.

And both of you have similar fields of work which makes communication and compatibility so much easier to handle because both your interests and passions in life align along the same direction.

But as perfect as the scenario may seem, is it all pretty and rosy?

[Read: 15 very obvious flirting signs between a guy and a girl]

Dating a boss and your love life

There’s a lot of good in dating someone from the workplace, especially your boss.

The perks of dating them are plenty, and the time spent together, well that’s a lot too.

But as awesome as the pros of dating a boss can seem, it also does come with a big share of cons too.

If you aren’t dating your boss yet and just find yourself falling for them, think twice about it because you could be getting yourself into something that could be very complicated unless you set clear boundaries. [Read: 19 sure signs you may be falling in love with your boss]

And on the other hand, if you’re already dating your boss, well, it’s not all bad, just as long as you remember to keep a few things in mind while dating them.

Are you falling for your boss?

Falling for the charming boss is the easiest thing to do at work. You admire them, they inspire you and you long to speak to them because you subconsciously crave for their attention and acknowledgment.

But when you crave for their recognition and their words, it’s easy to misinterpret this as love or infatuation, especially when your boss reciprocates your feelings by flirting with you or by exchanging sneaky glances at you now and then. [Read: 13 lusty signs of sexual attraction to keep an eye on]

It’s natural and you don’t have to hate yourself for it. It’s almost always not even your own fault, you just want to prove that you’re a good employee by winning their praise. But in your pursuit of trying to impress them, you may lose yourself and end up flirting with them and falling for them.

Should you really date your boss?

Office romances are frowned upon in most places, but workplaces still stir up a lot of romances and emotional affairs all the time. [Read: 18 signs you’re having an emotional affair at your workplace and don’t even know it!]

Dating a coworker who’s in the same level may be easier to handle, but dating someone like your boss, well, that’s just not the safest best in the world.

No matter what your true intentions are, everyone would generally assume you’re trying to catch the boss’s fancy just to get ahead at work by using the boss. But even beyond the opinions of your colleagues, the most important thing you need to discuss with your boss is whether you should keep the relationship a secret or bring it out in the open.

And that decision too, can have a big impact on your life. [Read: Reasons why a guy may want a secret relationship with you]

Having a secret relationship with your boss

Secret relationships seem safe. It’s a secret, the idea is exciting and no one in the world knows anything about the secret office affair. But a secret relationship can also cause insecurities to creep in.

You’ll never know if you’re the first, the last or even the only one your boss is having a flirty thing with. Your boss may know just how much attention they’re getting, and they may use it to their advantage.

Sometimes, bosses can be discreet, flirty and create circumstances to get you to fall for them. But while you may think you’re falling for your boss because of how awesome they are, in many circumstances, your boss could just be playing you and the circumstances to get you to fall for them.

If you’re having a secret relationship with your boss, and are certain you’re the only one they’re in a relationship with, that’s good for you. But if you ever feel like you’re being cheated on or being used, it’ll only leave you more confused and devastated because you can’t even confront anybody about it! [Read: 22 early warning signs of a bad boyfriend]

12 tips to keep in mind when you date your boss

Dating your boss isn’t all bad. There’s every possibility of a perfect relationship blooming out of it too. But all said and done, it’s always better to be safe than sorry. Here are 12 things you need to keep in mind when you date your boss or get friendlier with them.

#1 Draw the line. Don’t mix your personal and professional life. You may be dating your boss, but that’s no excuse to take advantage of your relationship status and use it in your workplace. Don’t bring love into the office when you’re paid to work. Even if it doesn’t affect your boss’s or your productivity right now, it will very soon. [Read: Love or career? - How to make the right choice]

#2 Stand up for yourself. Yes, you’re in awe of your boss. And you may even feel like the lucky one for being picked out of the entire group. But don’t let your admiration and reverence stop you from taking a stand in your personal life.

Just because you’re dating your boss doesn’t mean you have to say ‘yes’ or ‘no’ as per their wishes even in your personal life. If you give your boss this allowance, they’ll inevitably end up using you or walking all over you with their expectations and demands.

#3 You’re an equal. As tricky as it may seem, separate your professional and personal relationship with this person. In the office, yes, you’re their subordinate. But outside of work, feel like an equal and make sure your partner treats you that way too. If you ever feel disrespected in the relationship outside of work, talk about it with them. [Read: 16 reasons why you're always the one who's taken for granted]

#4 Public display of affection. When you fall in love with someone, it’s hard to stop blushing, exchanging flirty eye contact, or giggling each time both of you walk past each other. But that has to stop, at least in the public eye. It’ll only make you look silly at work. And more importantly, it’ll give more of a reason for your peers to hate you.

#5 Your life could get worse. Dating a boss always puts you in a tricky position, a vulnerable spot where you need to depend on your boss’s stand and their emotions if things ever do get bad between the both of you.

If they’re angry with you, they could treat you badly or ignore you at work. And you would inevitably do the same outside work. And a petty fight could turn into a game of egos where your partner tries to dominate you at the workplace, and you fight hard to retain the domination after work hours. And that will never lead to a happy ending! [Read: 12 real signs of true love in every relationship]

#6 Your peers may think lowly of you. If your colleagues find out about the relationship, they’ll always watch you with a wary eye. They may associate all your successes and promotions with the fact that you’re dating the boss, and they won’t credit your own efforts. And each time you slip up, they may convince themselves that you were let off easy only because you’re dating the boss.

And eventually, all you’d see is a bunch of disgruntled colleagues who hate you and hate the workplace because they believe they’re being treated unfairly by the boss!

#7 Accidental slipups. You may blurt out office gossip or harsh comments exchanged by your colleagues to your partner, who’s also your boss. And as much as both of you want to separate office and romance, your boss may still make decisions or judgments based on the things you hear and say. It’ll be awkward for you to say something, and yet, it’ll feel weird to hide the gossip too! [Read: The right way to end an affair and get over it completely]

#8 Office gossip. People at work love a bit of gossip, because there’s not much going on at a workplace other than work and any interesting news is definitely worth talking about. Once the word spreads that you’re dating your boss, you’d be known less for the person you are, and more for the fact that you’re dating the boss.

And every time there’s any interaction between your boss and you, you’d always have a lot of colleagues watching the both of you sneakily just to get more fodder to gossip behind your back. [Read: 10 types of toxic friends you need to avoid in your life]

#9 Jealousy at the workplace. Your boss would definitely be interacting with several of your colleagues and other people too. And if you see that they’re spending a lot of time with someone else or even publicly flirting with them, it may hurt you a lot. You may even start feeling more possessive and bitter each time you see that. And before you know it, you may end up trying to control your partner or find yourself telling them how they should behave at work.

#10 Is it a secret? A few workplaces are against office relationships, and a few more have clauses where relationships have to be reported. But even if there are no rules in this regard at work, can you tell your colleagues about it?

Letting the word get out may make your coworkers jealous and they may even hate you for it. And on the other hand, keeping it a secret would lead to a lot of insecurities because you’re giving your boss a free pass to do whatever they want or meet and flirt with anyone they want during work hours *because it’s all a part of their job!*. There’s no perfect answer here, but this is something both of you need to decide about and set clear rules together. [Read: 10 casual relationship rules to keep it just casual]

#11 Coworker rivalry. You could keep your romance a secret, or you could make it public. But what do you do when a coworker starts to fall for your boss? If you find your boss and this colleague bonding over work or having a laugh when they’re together, can you handle it without losing your cool? You can’t stop them from communicating, and neither can you intervene without making the workplace seem like a personal affair. Can you handle that? [Read: Does he love me? - 20 sure signs to read his true intentions]

#12 When it’s over. I wouldn’t want to be the bearer of bad news, but this is something you do need to consider even if you’re in a perfectly happy relationship with your boss. The future is unpredictable, and even if it’s just for a moment, have you thought about what would happen if both of you eventually break up or if the secret comes out in the open? [Read: 10 worst people you can ever have a one night stand with!]

If you think it’s worth the trouble, the safest bet when you’re dating your boss is to start looking for another workplace or a new organization to work for. By doing that, you won’t have to bear the brunt of office gossip even if you publicly date your boss. And even if things don’t work out, you don’t have to deal with any uncertainty of your job or prospective promotion because of your unpredictable ex!

[Read: The 9  relationship stages all couples go through]

Dating your boss can be thrilling and exciting. But if you’re not mentally prepared for it, or if your boss isn’t really serious about the relationship, it’ll do more damage than good for your life, both professional and personal.


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Have your say!
  • uche vivian
    October 4, 2013 | Permalink |

    MY God! Your article is great. it happened to me. In my case, we were dating before I came to work with him. The Jealousy is just too much and I am considering leaving. The painful part is that my colleagues have succeeded in telling my boss wrong info and gossips about me and he is so sad and he believes them. He always spits me at all times and I have decided to take a walk as well as to end the relationship.

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