8 Questions to Ask on a First Date to Discover His True Intentions


My name is Ashleigh and I’m addicted to audiobooks. You may wonder what this has to do with first date questions and I’m about to tell you. I signed up for Audible last year to listen to books when I traveled to Cancun. I thought I’d pay for one month and then delete it after I returned. Well, it has been 6 months and my account is still extremely active. I find myself looking for book suggestions to use my monthly credits on. So far, I’ve listened to books narrated by Gabrielle Union, Tabitha Brown, Will Smith, and Taraji P Henson. This week, my monthly credit was used for Judge Faith Jenkin’s new book entitled Sis, Don’t Settle.

Questions to Ask First Date

In this book, Judge Faith goes through her journey of being single way past 30 when everyone told her she was basically trippin. Instead of listening to outside influences telling her to just get a man, any man, get married, and have kids; she decided to wait for what she wanted. Not just what she wanted, but what she needed to be happy. I haven’t finished the book but one chapter stuck out to me. The chapter on first dates and how to uncover your date’s intentions. I felt this was really relevant to what I write about on this blog. I do believe dating is a skill and if we master the flow and ask the right questions, we can avoid falling for the many men we should avoid. Here are 8 questions to ask on a first date to uncover his true intentions.

1. What are you most excited about in your life right now?

This question helps you understand more about his values.

2. Where do you see yourself in 10 years?

This question helps you to see if marriage or kids is in his plans.

3. Would you consider yourself healed from your past?

This is self-explanatory. No one wants someone bringing unhealed trauma into a relationship.

4. What are your spiritual or religious beliefs?

Not everyone cares about this question but it’s good to know if you have an atheist in your midst.

5. What are some of your biggest fears?

This helps you uncover vulnerability levels.

6. Who do you look up to the most?

Who a person looks up to says a lot about their character. If his role model is Future, then run.

7. What are the roles of a husband or wife for you?

This is very important because if his views of marriage differ from yours, that could cause an issue.

8. What are you like when you’re angry? How did you handle disagreements?

How conflict is handled can make or break a relationship. Hopefully, he’ll be honest.

After Date Questions

These are questions to ask yourself so you don’t get so caught up in feelings that you lose your logic.

How did I feel in his company?

What did I learn about him and his character?

What am I going to do with the info I have now?