What's your problem?

Q: Should I tell my assistant I love her? I am in love with my PA. I am 45 and divorced and my PA is a confident, single woman in her mid-30s.

by Jeremy Bullmore
Last Updated: 31 Aug 2010

We have worked together for five years, and know each other fairly well. Would it be entirely inappropriate to let her know how I feel? I don't want her to think that I'm sexually harassing her.

I hope I'm wrong about this, but I think you should prepare yourself for disappointment. You've worked together for five years, seeing each other every working day - both of you single, so no problems of torn loyalties or guilt - and you still haven't the faintest idea how she feels about you.

It's possible, of course, that your masterly impersonation of Professor Higgins has convinced her that, since you clearly see the relationship as a strictly professional one, she'd better keep her own feelings well hidden. But the chances are, I fear, that she just sees you as someone she's very happy to work with.

You can test this quite easily, and without much risk. Think of the next available anniversary - her birthday, your birthday, the day she joined you - and suggest you treat yourselves to lunch. Don't get gooey: no roses or romantic restaurants, just a thoroughly agreeable lunch with a decent bottle of wine. Don't rehearse impassioned sentences in your head, say nothing that you (or she) might live to regret; just drink to your mutual tolerance in working together for a whole five years. From her response, however subtle, you'll be able to detect easily enough where the frontiers lie, and whether or not that's where she wants them to stay.

If you move too far too fast, the risk is not that she'll feel you're harassing her; more that she'll feel embarrassed and a little guilty that she can't return your feelings. But I repeat: I hope I'm wrong.

Please address your problems to Jeremy Bullmore at: Management Today, 174 Hammersmith Road, London W6 7JP. Or e-mail: management.today@haynet.com Regrettably, no correspondence can be entered into

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