How to Date Your Boss

Dating, relationships, partners and everything else that comes with them, are never simple and are the source of a large proportion of all of our troubles and woes. This seems to be a big issue for a lot of us, and yet while we might wish that love and relationships were simple, it seems that most of us are actually constantly making the whole thing a lot harder on ourselves. For instance the old ‘we want what we can’t have’ routine. It’s tried and tested and we all know it to be true, but boy does it make relationships that much harder and leave many of us in a pool of unrequited love or pounding against the wall in frustration and jealousy.

Another example is having a crush on your boss and this is again something we can’t have or at least shouldn’t have. Not only does it mean jeopardising our own career, but also potentially there’s and the careers of your colleagues. At the same time it is frowned upon by most people, and also a tad… clichéd. All that means that a relationship with your boss could very well mean sneaking around the place and keeping things a secret and that’s an incredibly stressful and difficult thing to do. In other words it’s far from easy to date your boss but then again that’s probably the very reason it’s something we all want so much. Of course there’s also the chance that you are just in love with your boss and they are just a great partner for you, and the fact that they are in a position of power over you can also be somewhat alluring. That said though, even those in it for the most admirable of reasons probably have to admit that the challenge and the ‘forbidden’ nature of the whole thing makes it all the more appealing. Why do you do it to yourself?

Well once you’re hooked you’re hooked and there’s probably no going back, so instead of reflecting on the difficulties involved any further let’s look at solutions. Here we’ll have a good look at some of the ways that you can make dating your boss a little simpler once you’ve snagged them.

Check the Policy: You might find that there is no policy in your workplace against dating colleagues or your boss, and if this is the case then you can go ahead and be okay with it. If it’s not explicitly stated anywhere then you should try and see if there is a precedent for it within your organisation and as this might suggest that it’s okay. Of course it’s a difficult topic to bring up without giving the game away.

Be Subtle: If there is no reason for you not to date your boss from the company’s perspective then this doesn’t give you a license to be completely un-subtle. Being in a relationship with your boss is something that can upset your colleagues if they think it means you are getting preferential treatment or just trying to get a raise. Try and keep your relationship below the radar then whether or not you are ‘allowed’ to be in the relationship.

Quit Your Job: Okay so it’s a bit extreme and something that not everyone will be in a position to do. However if there are rules against you and your boss dating and you are really keen on your boss (and you are not as keen on your career), then quitting your job can be a great way to allow the two of you to be together in an open manner. However bear in mind that quitting doesn’t necessarily resigning and being job-less – you can be just as successful just looking around for work and applying to jobs while you maintain your current position – then simply transfer to the other job. Hopefully you can find a position that’s at a similar level.

Move Departments: If you aren’t willing to leave your job just yet then this can make life trickier. Even if you allowed to date your boss and your colleagues don’t know other complications can arise such as if your colleagues start talking about your boss and expect you to join in, or if your partner starts asking you to report back on your friends leaving you in a position where you loyalties are divided and tested. To avoid these situations then you should transfer to another branch or another department whenever possible so that you are no longer dealing with your boss directly. Many jobs will give you this opportunity. Make sure though that you discuss this with your partner so it doesn’t come across as hurtful that you’re moving away from them. This also prevents you from having the problem of spending too much time with your partner which can leave you with nothing to talk about potentially.

Separate Business and Personal: Before you find a solution to your predicament you may well have to deal with your partner in a professional setting at some stage and they might have to reprimand you or you might need to go to them for help. This can be awkward as you become unsure on how to act now that you are dating outside of the office, but remember to try and stay professional and just as they shouldn’t show you preferential treatment, nor should you expect it. You also need to be aware of the ‘reaction formation’ defence mechanism in which you can be overly harsh towards your partner in a bid not to be overly forgiving. Just try your best to act normal and don’t hold anything that transpires in the office against them outside of it.

Think About it and Talk About it: In any relationship it is important to discuss the pros and cons with your partner and weigh up whether you are a viable couple and could work together in a long term relationship. When your career is on the line this is even more important so make sure to talk through your feelings and your concerns with your partner and to tackle problems together. At the same time think long and hard about how much you want this relationship and whether you are willing to sacrifice your job for it if necessary. Make sure that you really are attracted to the person and not just their position and the situation.



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