Reader Dilemma: 'I have worked with my boss for 20 years and now he says he fancies me - what should I do?'

I’m single, I’ve worked for my boss for 20 years and though I’ve never really fancied him, he is kind, funny, clever and we’re good friends. A month ago, I got a letter from him. He said his marriage had been over for ages, his children grown up, and he loved me. He said if I didn’t feel the same he would never mention this again. I wrote back, rather primly, saying I wasn’t a marriage-breaker and we continued as before. But now, of course, I see him in a different light and would love to see if it would work. Should I tell him?

Yours sincerely, Sally

This man has opened a Pandora’s box, hasn’t he? And although you slammed it shut when it was first opened, you’re now fantasising about what on earth there might have been inside. You want just one more peek. I can understand it. It’s irresistible. But let me just give you a few pointers before you go ahead.

True, it might be that you take him up on his offer, fall deeply in love, he leaves his wife and you live happily ever after with even, perhaps, a new family. Bliss awaits.

But on the downside, could it be that this man is having a mid-life crisis? His children have left home, he’s bored, and he’s looking around for something new. His eyes have alighted on you – quite naturally – because you are the next closest thing in his life to his wife. But is it really you he’s in love with (he’s taken 20 years to declare this love, after all)? Or is this a moment of romantic madness?

Why hasn’t he already left his wife if he’s so unhappy with her? I know from experience, after receiving many letters from people in your position, that a lot of men hang on to their marriage as a kind of fail-safe in case the new relationship goes wrong. Before you agree to anything, you’ve got to insist he leaves his wife first. Too many people I know have had to experience the wretched situation of a man – or woman – dithering painfully when it comes to actually making the break. The way you can not be a marriage-breaker is to have nothing to do with the break-up and only enter the scene after the dust has settled.

If he does break up with his wife, she will, almost certainly, be devastated. So will his children. They may be grown up, but even adult children can suffer terribly when their parents break up. Most research has been done on the effects of divorce on young children, but older children can behave very unpredictably, taking sides, having nervous breakdowns... don’t be responsible for any of this. He must make the split long before he embarks on an affair with you.

Your relationship works beautifully as it is. It’s a boss and assistant relationship. If you were to be partners, you would be more like equals. It might not work. And also, your relationship as it is works against a background of his being married. Take that background away, and it changes. Imagine going to the theatre and have the backdrop of rolling hills removed. The play looks and sounds quite different against a background of boxes, pulleys, and stage workings.

Finally, if you go ahead and it doesn’t work out, you’ll have lost being with a lovely man eight hours of every working day. Do you want to risk that?

Steer well clear

If this man was serious about entering into a new relationship, he would free himself from his existing one first. After all, he claims his marriage is over, but I am assuming he is still married and living with her, as you told him in your letter you were not a marriage-breaker.

It sounds like he wants to have his cake and eat it. Steer well clear.

Simon Abbott, Stockport

Don’t risk everything you have now

Your letter seems to reveal an unstated intention: you’re so intrigued and excited by the potential of this affair that you’ve already made up your mind to proceed and are simply seeking encouragement, not advice.You’re not alone. Too few of us are able to resist such a temptation.

So, this advice will be hard to swallow: don’t do it! You risk your self-esteem, your integrity, your friendship, your job and, hugely important in the eyes of your peers and friends, your honour as you aid and abet a cheat. But then, you know all of this.

Graham Bailey, York

Life isn’t that simple

Bear in mind that if you start a different sort of relationship with anyone, and it doesn’t work out for some reason, it will probably not go back to what it was before. Life is seldom that simple. If you’re prepared to take the risk, wait until your boss has actually left his wife (which it seems he has not yet done) and has a new home of his own. You’ve done well to say you’re not a marriage-breaker, which is good. Even if he divorces, there will still be a relationship of sorts between him and his ex because of his kids, and as others writing to Virginia have been told, his kids will always be more important to him than you are.

You cannot guarantee that a relationship will succeed, but protect yourself against a quick fling (unless that’s what you want), by having a condition that he moves out of the family home first – though don’t actually tell him that you are imposing such conditions.

name and address supplied

It’s too convenient

This all seem suspiciously expedient. He’s been married for years, you’ve been single for a while, presumably. Now, you both may be looking to change that – but why, exactly, would you do this with each other? He should decide whether he want to stay married, and you should decide whether you’re happy being single, but the two are not really related. I say keep him as a friend.

N Whittaker, by email

I’ve moved into a flat with three other girls, and I thought we were all getting on really well. The only problem is that things have suddenly started going missing – a £10 note here, a ring there, food from the fridge – and I’m not sure, but I feel everyone suspects me, as the newest arrival. I feel most uncomfortable, and don’t know what to do. Whoever it is has made certain that they haven’t stolen anything from me, so I can see why they’re suspicious. I can’t confide in any of them because I can’t trust any of them! What should I do?

Yours sincerely, Annie

What would you advise Annie to do?

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