10 Key Questions To Ask On The First 3 Dates

As a dating coach for women over 50, I give my clients a checklist of things to do.


First you need to do some personal growth and reflection on your past.


Second, you need to master my “3H dating technique.” This includes designing the questions you are going to need to ask in the first 3 dates.


Lastly, you need to learn the art and science of a “difficult conversation." I addressed that last week.


Back to those questions you need to ask on the first 3 dates.


They are based on your 3H criteria. That is what you need for your head, heart, and hoo-ha. Your practical needs, how you want to feel and what turns you on.

Here’s an example of one dater’s 3H criteria:

The questions you need to ask to determine whether or not your person is a good match are called “spark questions.”

For some of the things on your 3H chart, you don’t need a question, you can observe the answer: eye color, height, how you feel in their presence.

As you get to know the person you also have to ask yourself some overall questions:

  • Is this a practical match? Does this make sense? Is this intellectually compatible?

  • Does it feel good?

  • Does this turn me on? Am I attracted? Do I want to kiss?

For some of these criteria (the deal breakers in the head category) you have to ask questions directly in the texting phase (not on a live date) so you can avoid going on any live dates with folks who do not match your dealbreaker.


Some issues are pretty specific. And if you have a particular issue like a disability, a health issue, a kink, a strong feeling about religion or politics, or the desire to be poly, please do yourself a favor: use niche sites so you can mingle directly with others who have the same interests or issues.

If your issues are more mainstream, like you have kids at home, certain lifestyle points that are really important to you, or concerns about certain bad habits, you may be on the more generic sites and still need to bring up topics around your deal breakers.

You’ll need to language your questions about these types of topics in a very specific way so as not to scare someone off but also to elicit an honest response.

Always lubricate! That means surround the hard topic with graceful grease, a kindness at the top and after you’ve said the hard part, and an invitation for authentic feedback.

Example:

It’s been lovely texting with you. You seem great. I know this is very particular but I was raised in X religion and it’s still super important to me. I don't think I could really be compatible with someone who did not share X belief/ Y practice. Can you tell me where you are about it?


Or

I’ve really enjoyed our chats. It seems like we have a lot in common and might be a good match. But there is one thing I have noticed is a deal breaker for a number of men and that is that I still have kids at home. I am a pretty dedicated mom and I prioritize them, though I am looking for a long term partner. What are your feelings about that?

Or

It seems like there might be a spark here but before we go any further I feel like I want to be upfront about a dealbreaker for me. I don’t want to waste your time if it’s an issue for you. In the past I dated an alcoholic and it turned out pretty bad. As a result, I hardly drink, and I am really not comfortable around heavy drinking anymore. I don’t think I could be compatible with someone who really enjoys this. I am sorry to be so intrusive so early on, but it’s only because I think you’re cute, would you mind telling me where you’re at about alcohol these days?

 
 

See how in each one I started with something positive and kind and ended with a request for genuine feedback? And in each one I framed my concern in a very “light” and non-accusatory, non-judgmental way? That’s important.

Okay, so let’s say your deal breakers are all green flags and everything you can tell from the profile and the texting and a video chat tells you that your head, heart and hoo-ha will be happy, you can proceed to a live date where you can really dig in on the attraction piece and the emotional connection.


Now it gets even more important to ask good questions.


Here are some don’ts:

Don’t say things too bluntly (this puts people off).

Are you bad with money?

Why did you get a divorce?


Don’t ask yes or no questions (this doesn’t give you the intel you need).

So, are you good with kids?

Do you get along well with your family?

Don’t ask questions that have an obvious right/wrong answer.

Who’s fault was the divorce?

Are you happy with your work?

You’ll learn a lot more if you ask unexpected, open-ended questions and you’ll have more interesting conversations! So memorize at least 10 good questions that help you get at the heart of what you want to know.

Here are some good examples to get you started on your list:

  1. What’s the most adventurous thing you've ever done?

  2. What do you love about your work? What do you wish was different?

  3. Money has been an issue with me in past relationships, how bout you? If so, what were the issues?

  4. How was this last election for you?

  5. What are your kids up to these days?

  6. What’s your favorite thing about your sibling and why? (repeat for parents, kids etc.)

  7. Who was your best teacher and what did you love about them?

  8. If you could have a super power what would it be and why?

  9. I believe all humans lie, what do you think? What’s a lie you caught yourself wanting to tell? Tell me a story of getting caught lying.

  10. What kind of travel do you like? Describe an ideal trip?

  11. What is your fave animal, least fave and why?

  12. What do you consider your greatest successes?

  13. What are you the go to person for in your friend group?

  14. What are your best learnings from past relationships?

  15. Does anyone still think they are in a relationship with you?

  16. I have XYZ dreams for my life, what do you think? What are some of your dreams?


You can pick from among these or design your own based on YOUR 3H criteria and what you want to learn about. But please stick to my rules. Make the questions open-ended, light and with no clear right/wrong answer and you’ll get the best results.

One last rule: Be ready to answer the same questions yourself. Practice your answers if you have to. Authentic exchange on interesting or vulnerable topics is what makes for a real relationship. It also helps you find out fast if you and the other person aren’t a match.

I hope you are sold on the importance of doing the work to come up with your Spark Questions. Please feel free to post your list in my FREE Facebook group if you want feedback.

I am forever rooting for your happily ever after!


Love,

 
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Why Do Men Talk So Much On First Dates?

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The New "Honesty Is The Best Policy" In Dating