50 Deep Conversation Starters for Meaningful Connections

Key Takeaways

• Deep conversation starters help you learn more about other people and forge closer social connections.
• Asking thoughtful questions about a person’s interests, memories, dreams, and values helps you get to know them better and builds trust.
• Ask open-ended questions, stay curious, and listen actively so that people feel comfortable and understood.

Deep conversation starters help you move beyond small talk and open the doors to more meaningful, honest, and emotionally resonant connections. These conversation starters often focus on hypothetical situations, past experiences, emotions, fears, dreams, and values. For example, deep questions might focus on a favorite childhood memory or causes that a person is most passionate about.

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Deep Conversation Starters to Get to Know Someone

These are some conversation starters that can help you get to know someone better:

1. What do you consider your best quality?
2. What’s one thing you can’t live without?
3. Who are your role models?
4. Which is your favorite movie and why?
5. Which song best represents your life?
6. What is your healthiest habit?
7. What is your worst habit?
8. What stresses you out?
9. What is your deepest fear?
10. When was the last time you cried?

Unfortunately, researchers have found that while people benefit from deep conversations, people often stick to small talk because they overestimate how awkward these conversations will be.

Deep Questions About Love and Relationships

These are some conversation starters that can help you have a meaningful conversation about love and relationships:

1. Have you ever been in love? What was your first experience with love?
2. What does love mean to you? How would you describe it?
3. What do you think about love at first sight?
4. What are your thoughts about the idea of soul mates?
5. What qualities do you value most in a partner? Why are they important to you?
6. What do you believe are the key ingredients for a successful relationship?
7. What do you consider a deal breaker in a relationship?
8. What is the worst date you’ve ever been on?
9. What would your ideal date involve?
10. What is your love language? How do you like to give and receive love?
11. What lessons have you learned about love from your upbringing? What are ideas about love that you are learning or unlearning?
12. Who are your relationship role models?
13. What are your long-term relationship goals? What does life and retirement look like with your loved one by your side?
14. Tell me about a time when you felt truly loved and understood in a relationship. What made it special?
15. Have you ever been deeply hurt or hurt someone badly in a relationship? What happened?
16. What is the worst disagreement or fight you’ve had in a relationship? How did you solve it?
17. What is your biggest regret from your past relationships?
18. What are your current relationships like with your ex-partners?
19. What is the most valuable lesson you’ve learned in a relationship?
20. How do you maintain a healthy balance between independence and togetherness in a relationship?

Questions About Dreams, Wishes, and Values

These are some conversation starters that can help you have a meaningful conversation about wishes, dreams, and values:

1. What did you want to be when you were young? 
2. What is your dream job now?
3. Where do you see yourself 10 years from now?
4. If you could have three wishes granted to you right now, what would you ask for?
5. If money weren’t an issue and you could do anything in the world, what would you do?
6. Which skill do you want to learn/improve on?
7. What does happiness look like to you?
8. What are the things you are most grateful for?
9. What are your biggest challenges right now?
10. What legacy or impact would you like to leave behind in the world? How would you like to be remembered by others?

Conversations About Childhood and Upbringing

These are some conversation starters that can help you have a meaningful conversation about childhood and upbringing:

1. What is your most cherished memory of growing up?
2. What is your relationship with your parents/siblings like?
3. What are qualities about your parents/siblings that you like and admire, and what are characteristics they have that are more challenging?
4. What was it like being the oldest/youngest/middle/only child of the family?
5. What were holidays or vacations like in your family?
6. How does your family celebrate important occasions?
7. What does “home” mean to you?
8. Which meal or dish reminds you most of home?
9. What was growing up in your hometown like?
10. Who are the people who have made you who you are today?

“Meaningful conversations help us understand ourselves and the people around us better. They involve sharing important aspects of ourselves, and actively listening to, validating, and connecting with others,” says Sabrina Romanoff, PsyD, a clinical psychologist and professor at Yeshiva University.

Meaningful Conversations vs. Small Talk

While small talk, typically casual and lighthearted, can help break the ice, it may not necessarily help you form a deep, emotional bond with someone. These are some of the differences between meaningful conversations and small talk, according to Dr. Romanoff.

Casual Small Talk

• Lighthearted

• Casual and fun

• Doesn’t need much effort

• Shields vulnerabilities

• Can be with just about anyone

• Establishes common ground and sets the stage for deeper connections

According to researchers, conversation is a useful source of learning and serves as a central part of society and culture. It allows people to:

• Communicate norms
• Convey morality
• Share knowledge
• Offer differing perspectives
• Create a shared understanding

At the same time, experts have found that people underestimate what they’ll learn from these conversations. This discourages them from participating in conversations and becomes an obstacle when it comes to learning from others.

How to Have a Meaningful Conversation

Dr. Romanoff shares some tips that can help you have a meaningful conversation with someone:

• Ask open-ended questions and invite the other person to describe what a situation was like for them or how they felt.
• Be vulnerable and share information about yourself. Consider sharing personal information first to gain the other person’s trust.
• Adopt an attitude of curiosity and genuine interest in what the person is saying.
• Be thoughtful and try to put yourself in the other person’s shoes to see things from their perspective.
• Listen actively and ask follow-up questions.
• Empathize with them and offer emotional validation, so they feel seen and heard.

Sabrina Romanoff, PsyD

Opening up to someone and modeling the type of meaningful conversation you hope to have is a great way to help make them feel emotionally safe and willing to do the same.

— Sabrina Romanoff, PsyD

You may feel nervous about trying to initiate deep conversations with a friend, loved one, or someone you don’t know very well just yet, but learning more about them—and allowing them to learn more about you—is a great way to deepen your connection and build the kind of intimacy that helps sustain relationships over the long term. The more you learn and the more you share about yourself, the easier it will be to have more intimate conversations in the future without feeling uncomfortable.

Verywell Mind uses only high-quality sources, including peer-reviewed studies, to support the facts within our articles. Read our editorial process to learn more about how we fact-check and keep our content accurate, reliable, and trustworthy.

1. Kardas M, Kumar A, Epley N. Overly shallow? Miscalibrated expectations create a barrier to deeper conversation. J Pers Soc Psychol. 2022;122(3):367-398. doi:10.1037/pspa0000281

2. Atir S, Wald KA, Epley N. Talking with strangers is surprisingly informative. Proc Natl Acad Sci U S A. 2022;119(34):e2206992119. doi:10.1073/pnas.2206992119

3. Connor Desai S, Reimers S. Comparing the use of open and closed questions for web-based measures of the continued-influence effect. Behav Res Methods. 2019;51(3):1426-1440. doi:10.3758/s13428-018-1066-z

4. Jonsdottir IJ, Kristinsson K. Supervisors’ active-empathetic listening as an important antecedent of work engagement. Int J Environ Res Public Health. 2020;17(21):7976. doi:10.3390/ijerph17217976

By Sanjana Gupta

Sanjana is a health writer and editor. Her work spans various health-related topics, including mental health, fitness, nutrition, and wellness.

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