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12 Tips to Keep in Mind When You Date Your Boss

dating your boss

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.

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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Sophia Strutt
Sophia Strutt
Sophia Strutt loves staring into the mirror, not because she’s a narcissist but because the mirror is the one thing she can rely on to smile back at her, even...
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8 thoughts on “12 Tips to Keep in Mind When You Date Your Boss”

  1. uche vivian says:

    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.

  2. Ibanesse says:

    I’m sorry, but this article is an enormous disservice to everyone who reads it. Let me make this clear: do not date your boss. Ever. Under any circumstances. It’s grotesquely unprofessional and unethical, and is 100% guaranteed to create a problem for you at work. Unless you marry the guy (and, let’s be honest, it’s nearly always a younger female employee with an older male boss), and that’s probably not going to happen, since odds are he’s at least two decades older than you, there is absolutely no way that this will end well.

    But let’s take a step back from “all about you” mode here for a moment. What about everyone else? Congratulations, in order to satisfy your own childish need for approval and gratification from an authority figure, you’ve succeeded in creating an intrinsically hostile work environment for everyone that you work with. They WILL assume you are the office whore, even if your intentions are pure, they WILL see any success you have as unfair favoritism, and they WILL assume that anytime you’re alone with the boss in their office that you’re having sex with them. And if you ARE having sex with them in their office, then you are genuinely disrespectful to your co-workers on a level that goes beyond belief. I know this is hard when you’re all aflutter, but please keep your co-workers in mind. They deserve better than to have to work inside your relationship or inside your sex life.

    Oh, and about it always being a female underling with a male boss… This article is very clearly written with that in mind, so let’s be blunt there, as well. Women have a hard enough time being taken seriously in the misogynistic business world as it is. When you start dating or sleeping with your boss, all you’re doing is playing directly into every horrible stereotype people have about women in the workplace. You are doing yourself an enormous disservice, and setting yourself up to be seriously damaged in your career. People talk. Especially older men who want everyone, and I mean EVERYONE, to know that they’re boning their hot young employee. Word will get around, even in a large city, especially within the industry that you work in. And the worst part is, that asshat will walk away after the relationship (inevitably) ends, getting high fived by his buddies and going right back to what he was doing. You will be branded a slut or a dumb bimbo. It’s horribly unfair, it takes two to tango, after all, but it is the nature of the beast right now. He will look like a stud, you will look like a pathetic little girl with daddy issues. Oh, and I hate to break it to you, but if a boss is so unprofessional that he would even consider doing this? I guarantee you that he’s done it before. …Possibly many times before. And you won’t be the last.

    For the love of God, DO NOT DATE YOUR BOSS. If you MUST date at work, only date co-workers in other departments that do not share a chain of command with. And even then, only if absolutely necessary. You deserve better than to become the office punchline, or for the most intimate part of your life to be displayed for everyone to see. There are three and a half BILLION other men on the planet. Date one of them.

  3. nightman891 says:

    Can anyone tell me if there is a rule on a manager dating the ex girlfriend of a subordinate? They have been split up for about 8 months.

  4. Iain says:

    Office gossip really made my life miserable. I didn’t date my boss, but am currently dating my supervisor and a lot of people saw it as me trying to get ahead in my job. That wasn’t the case at all because I’m pretty happy where I’m at now and I haven’t had a promotion at any point since our relationship started, but still the rumors and whatnot continue to circulate around the place. I’m thinking of finding another job altogether, but I doubt I’d replace where I am now. It’s a tough decision for sure.

  5. AMANDA BYNE says:

    The one thing I put to mind when I’m dating my boss is not to think that he could fire me and not to kiss his ass. I don’t want to be promoted to a position I didn’t deserve. If I date my boss it would be because I like him personally, not because he is my boss. If he dislikes the way I am and decide to fire me with no apparent reason, I can call higher management and file a dispute anytime. I ain’t scared of losing anything I didn’t deserve to lose. Everyone gets his or her own way in life and I just live mine out no matter what.

  6. for your eyes only. says:

    I love dating my boss. I get extra special treatment at work because of it. Sure, they become jealous but I don’t mind. I love dating my boss. He is really good to me and I really think this might be love now. I don’t have to work on some days because he would always make me have paid time off days. I literally work 2 days a week now for 12 hours only but I get paid like I work 3 days a week for 12 hours plus over time of 2 hours a day. Isn’t that amazing? I am richer than ever because of my boss. Once I marry him, I’ll even be happier. I ain’t no gold digger though. I really love him because he makes his best efforts to make me happy even though he might lose his job doing what he does, he doesn’t really care.

  7. AdminGirl says:

    Well, I have the biggest crush on my boss, this is not a big company, we are for the most part the only 2 in the office, he is the owner of the company and I am the administrative assistant, so I don’t have to worry about jealous co-workers but my biggest fear is if it don’t work out would he want me to continue working for him and would I want to continue as well. I love my job, besides falling for my boss it is the best job I have ever had. I really need advice because I really want to pursue a relationship with him.

  8. Socjologia Zagadnienia says:

    Being creative is one word a large number of people are made aware of but are not able to fully grasp. Being creative is related to inspiration, fascination, innovation, unique, inventiveness, ingenuity, resourcefulness and so forth. Sad to say, many individuals will want to copy from some one than be creative.

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