Date your boss

Should you ever date your boss?

by Fran Creffield - November 22, 2012

Do you have the hots for your boss? Do you look forward to going to work every day in the hope you will get some time alone together? It is a natural phenomenon but is it ever a good idea to follow through and date your boss?

Power can be extremely attractive so it’s unsurprising that many of us harbour a secret crush on our boss. But should you ever act on it? We investigate

People in positions of power can seem very attractive. Most people had a crush on a teacher when they were at school and the cliché of the boss having and affair with his secretary is a cliché because it happens with startling regularity.

There are many psychological reasons why you might develop a crush on your boss – most of us spend the majority of our week in our work environment so it could simply be the amount of time you spend together. If you are working on shared projects, chatting about work and life and having lunch together it is natural you will develop a good working relationship but whether that should ever be followed through with dating is a different matter.

A no-win situation

Starting a relationship with your boss puts your job in a vulnerable position whatever the outcome of the relationship.  If it doesn’t work out the chances are that one or both of you are going to be left with hurt feelings. As you will still have to work together these hurt feelings can make it very uncomfortable for everyone. If your boss is the one feeling hurt or rejected they could make your life intolerable or maybe even find a reason to fire you. If you are the one who is left feeling sore then being told what to do by the person that hurt you is never going to be easy.

If things do work out and you stay together then people are going to find out – even if you are really discreet – and it could jeopardise your career in different ways. Any promotion or pay rise you get might be viewed with suspicion by co-workers and you could lose their friendship and respect if they think that your relationship was a step on the career ladder.


Even if your co-workers are OK at the beginning about you and your boss being close you mayfind over time that even ones you considered to be your friends start getting jealous because they interpret any good praise or treatment you get from your boss as suspicious rather than something you have earned. This can work the other way too and they think that you only work as hard as you do because you want to impress the boss.

However it plays out it will, over time, undermine your career as it is almost impossible to keep personal and private lives totally separate. Where power and authority are also involved it can become very difficult to tell what attitudes and treatment belong in your working relationship and what belongs in your personal relationship.

Conflict of interests

Many companies have policies about staff relationships because of the conflict that can arise. Even if your relationship goes on to become a serious one it is still likely to cause a conflict of interests for both of you. Your boss may find themselves having to put the company interests before their personal interests and this can impact on the relationship as a whole. Given the current job market you would both be wise to put the welfare of your career and position ahead of any feelings you have for one another unless you are sure they are serious.

If you are sure that it is more than just a crush

The best thing you can do if you are sure your feelings for each other are genuine is to get a new job. Once you are established in a new company then you will be free to pursue an open, honest relationship with your former boss without any risk of jeopardising either of your careers.

If it is too late for that and you are already involved with your boss remember:

– Try and maintain a professional standard in your work no matter how strong your feelings are – this will help avoid you getting into trouble with the company.

– Be discreet and never discuss the details of your dates with other work colleagues.

– Don’t conduct your relationship on company time.

– Don’t use your expense accounts for dates or use the in-house email systems for personal correspondence.