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Top Ten Questions to Ask Your Date

Top Ten Questions to Ask Your Date

Great conversation starters you can use on a date.


Navigating the dating scene today can be a real challenge. Pulled and distracted by the constant multi-tasking that fills most of our days, a meaningful conversation can feel like an unreachable goal. Here are ten questions you can use as great conversation starters. You never know where a powerful question will lead to.

  1. If you could plan an ideal day and money was not a limiting factor, what would you do?

  2. What are your top three priorities?

  3. What was the best part of your home growing up? What was the most difficult part?

  4. What are you curious about?

  5. Who are the three most important people in your life right now?

  6. What do you think are the building blocks of a great relationship?

  7. What do most people not know about you?

  8. Who have you learned the most from?

  9. What are three truths that you would leave behind if they were your only legacy for your family?

  10. What have you always dreamed of doing?

These questions will sometimes reveal glaring incompatibilities, like one person who said his dream was to travel around the world while his date preferred to forever stay within the comfort zone of her hometown. And some people discovered that they share many core values and beliefs.

Add your own suggestions for good questions to ask on a date in the comment section below.

October 26, 2016

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The opinions expressed in the comment section are the personal views of the commenters. Comments are moderated, so please keep it civil.

Visitor Comments: 3

(3) Yehoshua, November 2, 2016 1:04 AM

New SHidduch Group on Facebook

I just started a new Matchmaking group on fb for the YU-Modern Orthodox type. Feel free to change if you subscribe to that kind of Philosophy! Here's the link:

(2) jim, October 31, 2016 4:37 PM

is it 'always' too late?

i'll give them a try!

(1) Canuck, October 31, 2016 12:07 AM

Wonderful advice, Sara!

So where were you when I needed you 55 years ago?

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