Deep Questions to Ask to Quickly & Deeply Connect With Someone

living life quote Try to be a rainbow in someones cloud

Want to deepen your relationship with someone? Maybe you want to know better or connect deeper with your boyfriend or girlfriend, a boy or a girl you have a crush on, or with your friends or just the people around you?

You can learn how to have a deep conversation with them.
And this is the best social skill you can have.


According to social psychologist Arthur Aron, pairs who discuss deep questions are more likely to have a meaningful relationship as compared to those who keep small talks.

Even though many questions may sound general and it may only provoke small talk, the responses may be very revealing. The answers to these questions give you an idea of a person’s inner nature. Sometimes, asking personal questions will tell what an individual hides from others.


If you want to know someone beyond his basic and superficial information, then you need a list of deep questions to ask. Deep questions do not only help you to know others better, but you can also use them to know yourself better and find your purpose in life.

If they work so well it’s because they trigger emotional reactions, or high value oriented thoughts. They push the person to think with their brain and heart in order to find a relevant answer. It’s also rare to be listened by someone, and just the fact that you take the time to show interest and patience to someone is already a good feeling to someone nobody listen to!

Relationships are the most important aspects of our life. So, we have made a list of deep questions to ask someone to foster intimacy in your relationship.

Ask these 35 questions to someone you want to know better.


1. What do you miss about being a child?
2. If someone gives you enough money to start a business, what kind of business you will prefer to start?
3. If you could go back to your past, what one piece of advice would you prefer to give your younger self?
4. What is something that you wish to do in the next year that you have never done before?
5. What is your favorite memory with me?
6. What thing makes you happy?
7. What or who has impacted your life the most?
8. In which way do you best connect with others?
9. What are the five important things on your to-do list?
10. What matters most to you?
11. What is the best advice you have ever gotten?


12. Who do you trust the most?
13. What are the three things you are grateful for right now?
14. What is the craziest thing you have done in your life and would you love to do it again?
15. What’s your favorite family tradition?
16. If you have a chance to go back in the past, what time period would you want to go in?
17. What is your favorite quote?
18. What is the most valuable thing in friendship?
19. What was your favorite place to go as a kid and why did you love it?
20. What is your biggest goal for this year and how will you work to achieve it?
21. What was the first thing that you purchased with your own money?
22. What are you curious about?
23. What are the five things you think we have in common?
24. What are your top 5 strengths?
25. What are the three topics that you like to talk about?
26. What is your earliest childhood memory?
27. In what situation do you feel more comfortable to share your perspective?
28. Who is your ideal person?
29. How do you behave in anger?
30. In 10 years, what would you want to be?
31. What are the top three places on your list where you want to go?
32. If you have an opportunity to have any job you wanted, what will it be?
33. Tell me about a day that you will never forget.
34. What do you think about most?
35. What are those moments in your childhood that have changed you?



• Are you looking for commitment?
• What is more admirable between a stay at home mom and a career-driven mom?
• If you could pick a song, which do you think best suits our relationship?
• Would you consult me before buying me an expensive gift or would you rather surprise me with one?
• What was your first impression when you met me?
• Which fictional or real couple reminds you the most about us?
• At what point did you realize you wanted to be with me?
• Would you rather leave a great impact on your family or a big impact on the world?
• What do you appreciate about me?
• What is something you will never compromise about?
• What three things do we have in common?
• What outstanding differences exist between us?
• Should a proposal be a private intimate moment or a grand public display?


• What is your happiest memory?
• What is your most terrible memory?
• When did you last shed a tear?
• What were some of your childhood aspirations, and have they changed ever since?
• When was the first time you were deeply in love?
• What is your biggest insecurity?
• When was the first time you said I love you?
• If you had the chance to change anything about your past, what would it be?
• Is there anything you don’t want your family to know?
• How have you changed since your childhood?
• What are some lessons in life you had to learn the hard way?
• Which tradition you had as a child would you want to do with your kids at one point in the future?


• What is your hidden talent?
• Do you collect anything?
• Do you have any superstitions?
• What is your favorite theme song?
• Would you want to go on a silent retreat?
• Sometimes do you feel like you had a past life?
• Which three foods would you choose to eat for the rest of your life?

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