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Questions to Ask on Your Date

Questions to Ask on Your Date

A practical tool that could change your dating destiny.


My assistant Karen was in her mid-thirties and at the end of her rope with dating. She had been out with so many men who, for one reason or another, weren’t acting like a mensch. “He never called back after he said he would,” “he only talked about himself,” “he had only one thing on his mind…” etc., etc.

Karen is a great person; caring, bright, honest, spunky, and she has good values. Any man would be lucky to marry such a person. Yet nothing was moving her towards the chuppah. So she was done with dating. Ready to live out her life finding other pleasures besides marriage.

Because I was a few years older and happily married for ten years, Karen would often share her dating foibles with me.

And one day she told me she happened to meet someone at a holiday party. “He seems like a good guy, but can I stand one more failed date evening? Should I go out with him?”

I asked her to describe the new guy to me. This one really did sound like a good guy. A good communicator, respectful, happy disposition, decent looking.

“I’ve got an idea. Are you ready to take a chance and let your date know that you’re not just ‘sport dating’? Are you ready for a date where you’ll spend the time getting to know the ‘real him’?”

After dozens of typical ‘dumb dates,’ she knew sitting in a dark room watching another movie and having a drink in another dark room wasn’t getting her any closer to marriage.

“Take this card and play the dating game.” I handed her a card with 10 questions.

“It’s super easy to play. On your next date give him this card and ask him to choose two questions which you will answer. Then you choose two questions for him. You can’t ask more than two questions per date.”

Here are the 10 Questions:

  1. What two activities really energize you?
  2. What’s an accomplishment you’re most proud of?
  3. What book or movie had a great impact on your life?
  4. What two traits in your future spouse are most important to you?
  5. What part of yourself would you like to improve?
  6. What do you like to talk about (with people close to you)?
  7. Who is your most inspiring role model? What about him/her inspires you?
  8. What would you like me to know about you … that I may not have seen yet?
  9. What do you often wonder about?
  10. What character trait in others really bugs you?

“You game?” I asked Karen.

“I’m intrigued. But don’t you think asking questions like this turns the date into some kind of formal interview? I’m afraid it’s a turnoff.”

I reassured Karen that I knew from experience with other singles that this works. “Yes, at first it’s a little awkward. But if her date is dating for the right reasons, he’ll go along with it. The way he responds is going to be revealing. If the questions spark great conversation, that’s a good sign for a second date. If he’s not interested, you probably shouldn’t be either.”

“Okay, I’ll give it a shot,” she replied. “What have I got to lose? If he doesn’t go with my straight talk, he’s not the right guy.”

A few days later she popped by my office for a debriefing. “We went out and the date was fantastic.”

To make a long story real short, they kept going out for a few months until one morning she walked into my office with one huge smile.

“What’s up?” I asked her.

“He took me to the restaurant we went to on our first date and pulled out a card with 11 questions. The first 10 were funny. Question 11 was: “Will you marry me?”

Click here for a PDF version of the Dating Game Card.

January 11, 2014

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Visitor Comments: 25

(14) Me from Eretz Yisroel, March 21, 2017 8:29 PM

This story made me cry.

And I loved the questions edvice. Thank you.

(13) Bobby5000, October 3, 2014 2:09 AM

Trick questions

To Yamato and others, they are actually trick questions for a successful date. For example, take 1.What two activities really energize you? The right answer on most dates, is I like ... but tell me what you like. You seems really interesting and I'd love to hear more about the things you do and like. Rambling on about yourself is a pathway to failure and no I am sorry I'm busy when you ask her out on a second date. At a minimum the successful dater, shares conversation, shows genuine interest in the person he or she is with, and tries to shift the conversation to things they like. Read How to Win Friends and Influence People which is probably as good a roadmap for a date as there is.

(12) Dru, January 19, 2014 6:21 PM


Great questions for the 20/30-somethings who want to get married. But for the 60-somethings who don't, maybe noir.

(11) jay, January 18, 2014 1:55 PM


Very interesting. I think if the person does not take it as a joke then there is a real chance of sucess, one way or another.

(10) Anonymous, January 17, 2014 7:41 AM

As a male, how woul I stack up in this game?

1.Writing and building jewelry.
2.I got to deliver a scientific paper.
3.Yamato 2199, awe-inspiring bravery and compassion there.
4.Patience and empathy.
5.Trying to see past the duty of Judaism to some of the joy.
6.Gardening and cooking.
7.Mother Theresa. Her overwhelming dedication.
8.I have no family I can introduce you to. They're all dead.
9.Does God actually care about individual Jews or only about the Jewish People as a whole.
10.Any person who treats anyone or anything living cruelly is my unfriend forever.

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