21 Amazing Questions to Ask a Man on a Date

How can you discover who a man really is and find out how his mind works when you’re just getting to know him online or within just a few dates… all without coming across as if you’re interrogating him?

This can be a big challenge because you’re excited to get to know him and, at the same time, don’t want to waste your time if it turns out you’re not compatible.

Today I’m sharing with you the exact process I use with my private clients so you can get to know someone faster and more thoroughly. These thought-provoking questions will help you go deeper to discover a man’s true character.

While the questions may not seem like a big deal to you, the responses you’ll receive from men will be extraordinarily enlightening. When you ask these questions of a potential new love, be sure to take a deep breath and then listen with curiosity and objectivity as he answers.

I’ve even included questions about the women in his life. A man’s past experience with women, and how those relationships impacted him, will give you big clues into what a relationship with him will be like.

I always recommend asking the questions that are about him and his life before asking about other women. This will serve two purposes; you get to practice and build connection with him and he gets to feel more comfortable, gradually opening up to you.

One last note: Do NOT ask all these in one go – that will feel like an interrogation! Pick a few, or even just one or two, per date.

Okay, let’s dive in and explore the “21 Amazing Questions to Ask a Man on a Date”

  1. What is great about being a man?
  2. What is your definition of a successful life?
  3. What qualities do you like about yourself?
  4. What accomplishments are you most proud of?
  5. What do you want to be appreciated for?
  6. What qualities do you admire in other people?
  7. Who are your heroes?
  8. What did you learn from your parents?
  9. What is God or spirituality to you? How important is that in your life?
  10. If you could go on a dream holiday, where would it be?
  11. If you won the lottery, what would you do and how would your life be different?
  12. What do you love about women?
  13. What is the most extraordinary thing a woman has ever done for you?
  14. What did you think of me when you first saw me?
  15. When do you feel most at peace?
  16. Who do you look up to most in life?
  17. If you could change something about your life with a magic wand, what would it be?
  18. What do you respect about other men?
  19. If you could have one power (or super-power) that would make your relationships with women better, what would you choose and why?
  20. What do you think is romantic?
  21. What is the most romantic thing a woman has ever done for you?

Now you have it — the best questions to ask so you can really get to know a new man on a much deeper level. Remember, no interrogating! Just blend these questions into your conversations and then really listen to his answers. There’s no doubt that he’ll be intrigued with your questions and then you get to decide if his answers are what, and who, you’re looking for!

You love these questions, but you’re having a hard time attracting men to ask you out? Even though you might be nervous or skeptical – online dating is a great alternative! A LOT of my clients use this method (including dating apps) with excellent success. Which is why I created the Ultimate Guide to Online Dating where I support you every step of the way with getting started.

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