The Dating Questions You Need To Ask

So how do you know what dating questions to ask? I found out the hard way.

Remember that guy I was completely over the moon with? Well that bubble burst pretty quickly after the first 4 dates, we never made it to the 5th.

More dates were set 5 times and then cancelled 5 times, he cited work each time. My friends told me I was too nice and too forgiving but I still thought he was perfect – just obviously busy. Despite myself I became the hypocritical stalker that I’d criticised Alex for. I logged on to the dating site and hid my profile so I could see when he had last logged in. He had of course – very recently in fact, that very morning as he had sweetly texted me to cancel that evenings date.

The benefits and hazards of living in the same area as your date is that at some point, it is inevitable that you are going to bump into them. I was getting off the tube one Saturday afternoon to see a familiar silhouette on the platform. It was  a brief moment, but not brief enough for me to fail to notice he was standing there with his arm around a woman and the other arm around a little a girl of about 5 or 6. How cosy. Putting my head down and collar up I rushed off the tube, praying he’d not seen me. He had of course and my phone pinged within 10 minutes. I should explain. It’s not what you think. Sorry – I didn’t mention it. The wife. I should have. Can we meet so I can explain?

No, it is not complicated I thought as my phone rattled with more messages, it’s actually very simple. I had been there before with a pilot who forgot to tell me he had a fiancé tucked away in Denmark, and another boy I’d dated who was ‘trying to decide if he liked me more than his current girlfriend’. Tired of games and lies and disappointment I blocked his number.

I resolved on my next date to make sure I was better prepared. Armed with my dating questionnaire from the New York Times, I arranged to meet a gorgeous Irish guy. Extreme skier, climber, surfer, world traveller and entrepreneur, he was 48 and really honest, telling me straight out, he was not a commitment phobe he just hadn’t met the person he wanted to spend the rest of his life with (yet).

After some amusing emails, he suggested meeting for a drink on a Sunday night. Even better he thought the questionnaire was a brilliant idea. When I arrived at the pub, he was already waiting with his questions answered in full, with additional annotations as discussion points and a huge grin on his very cute face. I knew it was going to be a fun date.

It was a very intense experience but we dived into the experiment answering the following critical questions, plus some recent additions of my own. Given recent experience above I thought I should probably start by crossing off questions number 1 and 2 first.

  1. Are you married?
  2. When (if ever) it is acceptable to lie?
  3. Would you like to be famous? In what way?
  4. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
  5. Do you have a secret hunch about how you will die?
  6. If you could wake up tomorrow having gained any one quality or ability, what would it be?
  7. If a crystal ball could tell you the truth about yourself, your life, the future or
    anything else, what would you want to know?
  8. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  9. What is the greatest accomplishment of your life?
  10. What do you value most in a friendship?
  11. What is your most treasured memory?
  12. What is your most terrible memory?
  13. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  14. What does friendship mean to you?
  15. What roles do love and affection play in your life?
  16. How close and warm is your family? Do you feel your childhood was happier
    than most other people’s?
  17. Complete this sentence: “I wish I had someone with whom I could share 
  18. When did you last cry in front of another person? By yourself?
  19. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

Questions answered and by now several glasses of wine down, the best question was the last one as he leaned in and whispered to me “if it wasn’t a Sunday night I’d try and lead you very astray. Do you need to be up early tomorrow?” “No”. I replied…

PS: Single in the City is a new column by Miss X about being Single in the city. In case you missed, read the other columns here.


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