I have this charming boss who I have noticed has a soft spot for me. It is taking too long for him to make the move. What can I do to make him fall for me? He travels frequently. Please advise.
Kevin says:
This could be the best or worst career move you will ever make. If he is all-powerful, unscrupulous and randy, you could form a beautiful partnership where you fondle him in exchange for promotions. A bit like a wh*re that makes National Insurance contributions.
But what’s more likely – and apologies for being unromantic - is that you have sex a few times, it fizzles out, things become awkward and he fires you.
If you’re not that fussed about your job and you just really like him, by all means ask him out. Maybe you could say you’ve arranged a very important meeting for him – in your bed! He’ll like that. But I think the best quality you can show him is discretion.
Bear in mind that if he’s the kind of boss who sleeps with his PA, there’s a good chance he has ambitions to put it about elsewhere in your company too. So once he’s got want he wants, you may start cramping his style. He won’t want you hanging around hopefully at 5.30pm each day or eyeing him jealously while he chats to the new marketing intern.
But maybe I’m being too cynical about the longevity of boss-employee relationships. Look at Paul Daniels and Debbie McGee... no one thought that would work and now they’re one of the most glamorous couples in the world. And I guess there’s no reason why you can’t emulate Paul and Debbie if you genuinely like each other.
But I think you should let things simmer and keep the flirty relationship going for a while, rather than pulling out his rabbit too early and seeing your salary magically disappear.
Christine says:
Oh dear. This is dangerous territory, Alice. You are dancing on the precipice of the business/pleasure divide. One false move and you are head first into a world where people whisper about you around the watercooler. First you need to decide if you genuinely like him or if you are just trying to get a leg up, or over, the corporate ladder. This can be tricky and should only really be undertaken if you are really, really bad at your job.
In terms of work, there’s a chance you might lose some respect from him in the workplace if the lines are blurred and your colleagues will be careful about what they share with you if they know you’re ‘doing’ the boss. So before you throw all your paperwork on the floor and clamber over the fax machine to get to get to him, make sure you’re ready to cross that line. If the pleasure still outweighs the pain, then you need to make it a bit clearer that you like him. He’s your boss, he’s probably nervous that he’ll make a move and you’ll call HR and report him for being a sleazy cliché of a man. If there are no office parties on the horizon, suggest staying back in the office for some late night photocopying. I’d maybe do a copy of your p45 while you’re there, just in case.
14_Inches
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