Ten Questions to ask on your Valentine’s Day Date

It’s almost Valentine’s Day and that means it’s time to step up your game.

It’s time to have fun and share great moments with someone you care about without having to endure the awkward silence which is the hallmark of most terrible dates. Infact the only thing worse than an awkward silence during a date is small talk. Those are the terrible twins.

And it’s even worse if it’s a first date.

With first dates you also have to impress – you know what they say about first impressions and how it tends to stick. If he/she thinks you are not worth it on the first date, there is every chance that opinion will be the prevailing thought when the person thinks about you. Yet, mostly, we are probably not as bad as our first impressions usually implies (okay, some people are as bad, I know.) but the problem arises because of what is a “break in transmission” or what some term communications.

Knowing what to say on a date is important in having a really great date. And a great date tends to lead to more dates or even something more.
So, what are the things to ask without you coming across as probing or boring?

In that mind, I have some great questions for you to ask your date tomorrow. These are personal questions that reveal the person behind the face sitting across from you, and help to peel the onions slowly and reveal intimate things about them. These questions encourages expressions and helps you incorporate the other person into yourself, as you contrast their answers with yours, and in so doing forge a closeness without pretense. These questions make it possible to generate intimacy and know what motivates your date without being too pointed.

What works for first dates also work for second, third and even for the fourth date.

  1. Are you working on any personal passion projects
  2. What does a typical day looks like for you?
  3. What were you like as a kid?
  4. What sort of vacations do you love to take
  5. 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?
  6. If you could wake up tomorrow having gained any one quality or ability, what would it be?
  7. What, if anything, is too serious to be joked about?
  8. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  9. Given the choice of anyone in the world, whom would you want as a dinner guest?
  10. Name two things you think you have in control.

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