1 Can I have a raise?

Even the meek are set to inherit the Earth ahead of the guileless. Show your boss you deserve the raise instead of asking for it. Then negotiate, don’t plead.

2 Would you like to have children?

Possibly the most asked and yet intrusive question out there. On a date it’s too forward; in the workplace it’s illegal. But not as much fun as either of those sound.

3 Would you like to drive?

Why, in the name of all things manly, would you ever want to pass on your keys to the manmobile? The only exceptions to the rule: if you have lost the use of one or more limbs; you’ve been rendered incapable of steering; or if you’re falling asleep at the wheel .

4 How was that for you?

Caring? Nah. This has needy written all over it. Unless, of course, your superior technique has brought her out in a mini-fit of the Mariah Careys and you’re demanding a thank-you.

5 When’s the latest I can get this to you?

A sure-fire confidence burster to bosses/customers/whomever. It implies that your grasp of that invaluable tool, the margin of error, is non-existent. If anyone ever asks you this, lie and bring their deadline forward by a week.

6 Are you sure this is okay?

It’s only too good to be true when you stop to think about it. If we’re going to start raising questions at this point, why not just have done with it. Strap the gift horse into a dentist’s chair, fire up the drill and ask: is it safe? Carpe diem, always. Before they change their mind.

7 Are you a natural blonde?

It’s better to never find out if she’s guilty of bleach of promise. See also: “Are those your real breasts?”

8 What’s your star sign?

This is the sort of fluffy banter that women can trade without any worry, but coming from a man it sounds vaguely creepy. Or merely transparent. Like praising Baz Luhrmann movies, or enjoying the songwriting of Ronan Keating.

9 Do I look big in these jeans?

You’ve just lost man points. If you’ve put on weight, get back into the gym or start tying your running shoelaces more regularly. Don’t look for sympathy.

10 What would you like to do tonight?

In the early days of a romantic dalliance, benign dictatorships are very often successful – whereas anything that can be perceived as indecision will inevitably lead you to becoming single again (or watching crappy television shows featuring the Kardashians). It’s dinner, you’ve booked it and she’ll bloody well like it. See, sexy isn’t it?

11 So, how far along are you?

[Alternative: when are you due?] There is no real benefit to this question, and there are all kinds of penalties if you get it wrong. And trust us – you will get it wrong. If you do suspect a friend or colleague is expecting, wait for a female friend to ask first.