A gentleman’s guide to dating at work (without ending up in HR)

We turn to a dating expert to cut through the red tape of workplace romances

Office-place dating? File under ‘difficult’. There’s nothing quite so volatile as mixing your personal life with your professional life, with potential repercussions grave if things go south. But, if all succeeds, love amongst the paperclips and photocopier can be the most exciting and exhilarating of all. You’ll likely keep the relationship a secret, you’ll see each other all the time and you’ll never have to try to explain what you do for a living to your other half. It’s a win-win, right?

Wrong. Over the bright light of your new love looms the shadow of HR, threatening your happily-ever-after with reams of red tape, inter-departmental protocol and, in extreme cases, dismissal. As it’s such a thorny subject, we turned to Claire Certain, a dating expert from app Happn, to help us negotiate the minefield that is workplace dating – to ensure you never explosively set a foot wrong and come out the other size with your limbs, dignity and heart in tact.

Begin slowly - take your time and talk

A gentleman’s guide to dating at work (without ending up in HR)

Get to know the person first; it should never be out of the blue. Use social events such as Friday drinks or work occasions to chat a little bit; usually just through a simple chat you can get a clue if they are also interested. Take a little longer than you would do in normal life. 

Remember your professional persona is hugely important and you don’t want anything you do in your personal life to impact on this.  Once you know that there is a clear chance of a date where your crush has expressed an interest, simply ask – should they say no, you tried, just make sure you take it well. React nicely and don’t let your feelings show in the workplace. And of course, avoid being suggestive in any way until you’re 100% sure you’ll get the response you would like.

Use these tips to tell if she’s interested in you

A lot of the time it all falls on intuition. If you think there are little signals being sent back and forth then take it step by step, moving from team activities, to one to one coffee.  You will be able to tell if they’re not interested if they don’t want to come and, of course, each time you’re with them you’re getting to know them better and gauging their feelings.

"If you think there are little signals being sent back and forth then take it step by step..."

Remember, one of you will have to make the first move but it’s so important that you’re sure it’s want your crush wants too – never put them in an awkward situation, particularly in worktime. Appreciate that this will not be an easy situation regardless of the answer but if that person is becoming special it is always worth a go. Just make sure to be respectful and considerate.

Set some ground rules before you start dating

A gentleman’s guide to dating at work (without ending up in HR)

There are definitely a good few ground rules you should establish when you start dating.  For starters, keep it a secret, even from your office best friend, at least until you have been on a few dates and you know where it’s heading. No matter how into each other you are, never do anything inappropriate at work.

A secret squeeze of the hand is probably the safest but anything more and others seeing could risk your job.  Better safe than sorry, leave all of that until you get home. Also the power of anticipation will definitely act in your favour.

Check if you workplace has rules against relationships

Some companies have rules in place against workers dating and many individuals have specific personal rules where they don’t date at work.  I can’t highlight enough how important it is that you are confident the person you are making a move on likes you back.

"No matter how into each other you are, never do anything inappropriate at work..."

Setting your own rules for dating in the workplace are also paramount. Without those rules, miscommunication can cause issues and problems due to insecurity and lack of transparency. Ideally keep your relationship between the two of you for a while until it’s more defined and you know for sure it’s not just a fling.

If you break up, do it professionally

A gentleman’s guide to dating at work (without ending up in HR)

Breaking up is a tough one – more so in the workplace. I knew a few people who went through a difficult break up and one party had to change jobs. It is definitely a risk which should be considered before things start getting serious.

The best case scenario is that you remain friends and after a few weeks you’ll be able to fall back into the old routine.  The most important thing is to be kind to one another when you’re at work as it’s a difficult situation for the both of you. But, in time, you can return to being friends again.

Workplace romance going inordinately well? Why not learn how to take the next step with an engagement ring…

Further Reading