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Five Questions to Ask
During the Courting Stage

The Relationship Prescriber


Free Content


I would have entitled this originally five questions to ask on the first date, however, I think during the courting stage is better fitting in that sometimes people are nervous on the first date and you won’t necessarily be able to get past that wall. Good relationships take time so do not be discouraged if this happens…


1. What are five adjectives you would expect people to say about you whether they have known you for a long time or just met you? 

This question provides you with two pieces of insight. How the person sees themselves and how they think others see them. It may take time for the person to answer but this is a very deep, thought-provoking question that will shed a lot of light and perspective.


2. What would you say some of your defining moments have been in life? 

This question illuminates the person’s priorities and what makes them, them. It almost gives you the cliff notes version to their lives and what their priorities, struggles, and glorifying moments are. It’s always interesting to see will the defining moments be accomplishments? Overcoming obstacles? Really happy moments? Or moments of despair.


3. What have you learned the most in relationships? 

This question provides insight on the prospective partners ability to reflect, introspect, and what relationships mean to them. Are they someone who keeps repeating the same pattern? Do they take accountability? Is it a them vs the world type of mentality? What do relationships provide them as well? This question uncovers a lot.


4. What is something you wish you would have taken care of today that you regret you didn't? 

This question is the more superficial of the five, however it has a cutesy element to them and illustrates the person’s determination and priorities.


5. What does your ideal relationship look like for you? 

The ideal relationship shows you what the person is looking for, and gives you insight into what their needs are as well. Be careful with this question though. If our esteem isn’t high and we feel like we don’t match what they are looking for, we can be discouraged or subconsciously self-sabotage. Take what the person says with a grain of salt. People’s opinions change and we are constantly learning about ourselves from relationship to relationship. Illuminate yourself. Perhaps you have something they didn’t know they wanted. Nonetheless, it gives you additional insight into their ideal match.

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