How to Secretly Date Your Boss

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Naughty! You’ve come here for advice on how to date your boss in secret? So, how long have you two been at it? Not that I’m a gossip or anything.

I’ll just assume that you didn’t come here for criticism either, so don’t worry, we won’t say a word about how you’ve fallen for one of the biggest workplace cliches of all time.

The thing about secret relationships is that they are really hard to keep secret, so if you want this path you’ve set out on to succeed, you need to do your very best and follow every last bit of the advice provided here.

1. No googly eyes

I know, your boss is so hot you just can’t help but drool every time she or he walks into the room. However, if that room happens to be the room you share with your colleagues, you must try your hardest and toughest not to look up from your screen.

Keep those eyes fixed on the screen, that’s right! Was it a fly or was it your boss who walked in? Who knows? Not you, because you stared at your screen so hard, you couldn’t even blink.

If you are at the beginning of your secret affair, it can be really hard to look at your object of desire without lust in your eyes, which could prove to be risky if your office is packed with nosy colleagues who won’t have trouble putting two and two together.

What you need to do is pretend your boss doesn’t exist unless of course he or she directly addresses you (if you don’t look at them, then it’ll just be awkward, and your nosy colleagues will start making assumptions). So, if you do need to look at him or her just make sure you keep eye contact to a minimum and whatever you do don’t give them that sexy smile. Think of kittens dying if you must. Yep, it’s THAT important.

2. Social life: Farewell


Going out in public together will not be easy to pull off. The danger of someone seeing you will always be imminent, which will make both of you jumpy and ruin your night and, before long, it will also ruin your relationship.

So the easy way out here is for the pair of you not to go out.

Of course, if your boss is a multimillionaire who wouldn’t mind spending a load of money, then maybe you could get them to book that fancy Japanese restaurant you’ve been dying to go to, just for the two of you. Just make sure you are not too obvious about it because they might think you’re only doing it for the money and privileges.

If you do not work for a multimillionaire, just invite him or her over, for a homemade cheese platter, expensive wine (which I hope they’ll be the ones to bring, otherwise why even bother?) and a long (sure hope it’s long), passionate night in your boudoir.

Avoid going over to their place, unless you are familiar with their neighbourhood and know that there are no prying eyes there.

Otherwise, you can get them to book a fancy hotel room, preferably one with a built-in jacuzzi where you can drink Champagne to your heart’s content. Dating the boss should be made worth the risk, don’t you think?

3. Keep it a secret

As in secret, secret, which means NO ONE should know. Yes, I know that there’s this girl in legal who you share and bond with over lunch, but I’m afraid she can’t know you are dating the boss. Even if the boss isn’t her boss, she should still not know.

This relationship should be such a well-kept secret, that you should, at times, find yourself not being able to tell if it’s a fantasy or if it’s happening in real life. When that happens, you can simply go and look at all of the fancy gifts you’ve received from your secret beau, and you’ll remember that yes indeed, it is happening for real.

4. The world is your oyster

Doctor Who and ClaraMirror

The truth is that the only way you can truly enjoy your love for one another is if you are out of the country. What’s that? Did someone say conference?

If you are truly into this relationship, then you have your job cut out for you. Find a conference that’s relevant to your particular field, but don’t find a prestigious conference, find one that no one will have heard of for obvious reasons.

Now the real trick is finding a date that only you and the boss will be available to go on, and then ask your boss/lover to send an official email saying that the pair of you will need to attend that conference. Then play up the victim card, the boss is making you go, you had plans, there was the possibility of a second date with someone, and now you’ll have to cancel on them and so on.

If you’ve found true love in the face of your boss, what are you going to do? Deny yourself the possibility of a soul mate? Of course not, you have to give it a shot. So don’t let anything discourage you, but before you start the relationship, make sure you know what the employee handbook says about such relationships –just in case.

Have you ever had a secret affair with your boss? How did that work out for you? Share with us in the comment section bellow.