10 creative questions for a first date

10 creative questions for a first date

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Keeping the conversation flowing on a first date can be tricky, so why not come pre-prepared with a set of questions that take things beyond the mundane?

Getting yourself scrubbed up, well-dressed and on time is the simplest part of any first date – without a doubt the hardest task is breaking the ice when your prospective partner arrives. It’s far too easy to fall back on the standard topics of conversation – what do you do for work, for fun etc – without finding out anything of real interest about them.

Come armed with these 10 questions, however, and not only will the conversation flow like a fine wine, but you’ll also be able to judge if it’s worth making this more than a one-off encounter.

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If we had a private jet, which destination would you take me to and what would we do when we get there?
Question 1

How better to find out if you’re talking to an intrepid adventurer or a couch potato? If you are someone who likes to travel, but your date only wants a bog-standard beach holiday, then maybe make this drink the last before leaving.

What’s the best gift you have ever received?
Question 2

Was it a treasured family heirloom or a year’s supply of cigarettes? Granted, those are pretty polarised examples, but the answer should clarify the kind of things your date values most in life.

6 things you shouldn't say on a first date

Nervous about your first date? No matter how bad things you think things are going, here are 6 things you should avoid saying at all costs.

What is the funniest thing that has happened to you?
Question 3

Not everyone is a born a natural stand-up comedian. Nevertheless, a similar sense of humour is pretty good thing to discover if you want to move on to date number two.

If you became famous, what would you like to be best known as?
Question 4

No matter if your date responds ‘artist’, ‘pop singer’ or ‘scientist’, the answer to this question will allow you to learn something about your date’s value system. Although if they say ‘celebrity’, perhaps just make your excuses and leave.

If we could go to any restaurant in the world, which one would you go to?
Question 5

Combining both cuisine and travel, this is infinitely better than asking someone what their favourite food is. Keep an open mind and avoid being a judgemental foodie, although again, if they answer “McDonald’s”, maybe make like a banana milkshake and split.

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If you could wake up in a new home, what would it look like?
Question 6

Bigger, better, bolder: almost everyone has an idea of their dream home. You can get a good idea of how humble (a modestly-sized house) or ostentatious (a huge mansion) your prospective partner is.

Do you speak any foreign languages, or have you ever tried?
Question 7

This should give you an idea of how cosmopolitan and outwardly-looking your date is. Not everyone can speak a foreign language fluently, but plus marks must be awarded for any attempts to try and communicate in the local dialect when travelling or on holiday. The results might be amusing too.

If you ruled of the world, what would you do to change it?
Question 8

Louis Vuitton bags and iPhones for all or an end to global famine? Yes, this might sound like the sort of question you’d hear at a Miss World contest, but the answer will be revealing.

If you could invite three people – dead or alive – to dinner, who would they be?
Question 9

Would your date invite their three best friends, family members, or Elon Musk, J.K. Rowling and Serena Williams to be their dinner companions? There’s no right or wrong answers here.  

What was the most embarrassing moment of your life?
Question 10

Exposing your most uncomfortable experiences takes a lot of courage, but if your date has no qualms about broaching the subject, you can consider the ice between you well and truly melted. 

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04 2017 The Red Bulletin

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