What's your problem?

I work for a property developer in a client-facing role. I'm a recently divorced forty-something and have found myself deeply attracted to one of my new clients.

by Jeremy Bullmore
Last Updated: 31 Aug 2010

I've held back from asking her out on a date as I regard this as unprofessional, but I'm starting to feel as though I could be missing out on something wonderful. What would you advise?

A: I suspect you know only too well the sort of advice I'm going to come up with. As someone recently divorced, there's a hole in your life that you'd quite like to fill. An accident of work has brought you into regular contact with an attractive woman and provided you with a common interest.

You enjoy her company and would like to move things on. Only your concern about compromising a professional relationship is holding you back - and even that you're beginning to question.

Given all that, my instant reaction really has to be the boringly predictable one. Watch it. And not just because of the professional aspect.

Everything I've itemised above lowers your native caution. Like Annie Oakley, your defences are down. It's all too timely, too tidy and too convenient.

Having said all that, I don't rule out the possibility, to use your own words, of something wonderful happening. I just urge you to play it long.

Unless you screw up the professional side of your relationship, you have the bonus of knowing that you'll continue to meet regularly - so there's plenty of time to establish a couple of very important things. One: how solid is that feeling of yours? And two: what about her own feelings?

If you ask her out on a date, blurt out a few well-meant but irretrievable words and only then discover that she sees you as no more than an agreeable colleague and companion, that really would be a bit of a disaster - both personally and professionally.

So please take your time. You've nothing to lose except the risk of making a serious mistake.

- Jeremy Bullmore has been creative director and chairman of J Walter Thompson London and a non-executive director of both the Guardian Media Group and WPP. Address your problems to Jeremy Bullmore at: editorial@mtmagazine.co.uk. Regrettably, no correspondence can be entered into.

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