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65 Questions: The Quest to a Meaning Conversation

Updated on June 9, 2020
Arnaba Saha profile image

Arnaba is an ambivert. She is here to share her experience, knowledge, and strategies on interpersonal skills and relationship management.


Meeting new people, making small chats, or professional conversations is part and parcel of life. But do you sometimes feel the need to share a meaningful conversation with someone who has recently met? Someone you want to know more about them. You might have known a person for a long time but now you want to go beyond “what’s up” and “how are you”? If you want to strike some meaningful conversation during a lunch or dinner date, you need to come up with interesting, intriguing, and not-so-difficult questions for your partner.

These questions are designed to help you scratch the surface of your partner and delve into a deep conversation.

Some questions help you to reach a person’s inner world- their goals, dreams, and thoughts. These questions help you to build a bond and get to a person in a better and more insightful way.

Now let us find out the 65 questions that will help you strike a meaning and consequential conversation without being awkward:


Start your conversation by knowing their likes and dislikes. Knowing a person’s preferences help you to make out the basics of a person. Moreover, you don’t want to startle your partner at once by asking intimate questions in the beginning. But importantly, you have to come with follow up questions that will eventually lead to a fulfilling conversation.

How do you like to spend your weekends?
What type of music are you into?
Whats your favorite ice cream toppings?
Which were the last 3 show, you binge-watched?
Are you an introvert or an extrovert?
Given a chance, what would you choose- a Sunday at home with your family or a Sunday out with your friends?
Are you into audiobooks? What are you listening at present?
What’s your favorite holiday looks like? Why?
Whats your favourite quotes from a movie/tv show or book?
Do you have any pet peeves?
Whats your “go-to-retreat” when you are tensed or low?
What do you prefer during summers- blast the AC or sleeping by the window?
Whats your ideal birthday plan?
Which song always make your feet hit the dance floor?
Have you ever disliked someone or something but eventually changed your mind later?
Whats your favorite board game?
What do you prefer- coffee or tea?
How do you like your tea or coffee?
Whats your most prized possession and why?


Career forms a huge part of a person’s life. You spend hours either working or thinking about work and your future. Thus, it is but natural for your career goals, dreams, and current situation to shape the most of you. Try to find out how or what your partner prefers when it comes to his career aspiration. This will give your glimpse of the types of people he/she is.

What's the annoying aspect of your office?
What type of person are- “work to live” or “live to work”?
Are you happy where you are in your career at present?
What makes you happy about your job?
What do you think, how your 10-year-old self would react to your present job?
What's your favorite part of the workday?
What inspired you to get into your field of work?
What do you think is the best decision you made in your career?
Do you believe in “five-year plannings”? do you have one?
How do you separate your personal life from your work life?
Whats you take on workaholic?
Do you think it's possible to have work best friend?
What's the worst work advice you ever received?
What's the best thing you have learned in your current position?


Family is the most significant part of a person’s life. You will never find a better topic to get to know a person better. Ask about their family and relations to find out interesting, hilarious, or emotional stories. Within no time, your conversation will lead you to their connections, experiences, and family values. If you are really interested and considering to get married (maybe), then these questions will help you to get a clearer perspective about your partner.

Were you close to your family while growing up?
Whose your “go-to-person” in your family when you are low?Whose your “go-to-person” in your family when you are low?
What's your favorite family tradition?
What was it like growing up as the oldest/youngest/only child?
What trait of your family appeals to you the most?
What's the one thing that bonds your family together?
Do you have friends whom you consider family?
What makes you proud of your family?
What are your favorite memories with your parents/family?
Which character trait do you share with your parents?


Values are the foundation of any person’s life. Values guide them to live the life they are leading. Their values determine their actions, reactions, and decisions.

What is the definition of success for you?
Do you consider yourself spiritual or religious?
What makes you feel most accomplished?
Who inspires you the most in the world?
What would you like to do if you won a million dollars?
What attracts you to a person?
Is there any particle motto or piece of advice that you follow?
What makes you distrust a person?
What does a person need to do to earn your trust?
Do you believe in a second chance?
What line someone should never cross with you?
What's your definition of beauty?
Do you believe in soul mates?
Do you believe in life after death?
How do you react to a person who disagrees with you?


No, these questions do not concern the dream a person sees in sleep. Here, you will find questions that will allow you to know which dreams do not allow him to sleep. Dreams that motivates him/her to wake up in the morning and strive his/her way through various obstacles in life. You will get to know what gets him going.

Do you have ant regrets of not doing anything when you could have done?
Where do you see yourself in the next 10 years?
Who among the people you know presently would be there with you after 10 years?
What would be your three wishes if you had a genie?
What would you like to do if you found out this would be your last on Earth?


Some questions are more meaningful than their answers and others lead you to something more than just answer. Personal information can exponentially increase your intimacy with your partner. Be it a friend, boyfriend/girlfriend, or the person you are interested in; good conversations always lead you to stronger bonding and understanding about each.

Therefore, be ready to strike some meaningful conversation and get to know a person in a better and personal way. Put your guard down and confidently ask (or answer ) these deep questions for some intriguing conversation.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2020 Arnaba Saha


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