8 Questions To Deepen Your Friendship And Create Strong Bonds

Friendship is one of the most reliable pathways to happiness. But it’s not just the number of friends you have, in fact, your wellbeing and sense joy are also significantly impacted by the quality of your relationships. Importantly, there are specific questions that will inspire conversations to deepen your friendship and strengthen your bonds with others.

It’s especially important to be intentional about making friends and sustaining them—and also to ensure you’re developing the relationships that mean the most to you. When you have a few good friends, it contributes to your wellbeing as well as your physical and mental health—and even your likelihood to stay at your job and find satisfaction with it.

You may have plenty of acquaintances that you work with or can grab coffee with, but you also need a few people that you can go deeper with—the colleague you’ve gotten to know through thick and thin or the neighbor with whom you share meaningful experiences.

Questions to Deepen Your Friendship

So how can you deepen a friendship and enhance bonding and belonging? It’s key to ensure meaningful conversation and reciprocal sharing, according to strategies based on science. And one approach you can use is to inject questions into your discussions.

These are the questions that can help you deepen, develop and evolve a relationship. You can use them by keeping them in mind and bringing them into your conversations casually and organically. Or you can agree with your friend that you want to ask each other a question or two each time you’re together.

You’ll want to be sure the questions lead to conversation and mutual sharing—not a one-sided interview. And you’ll want to avoid taking yourselves too seriously—ensuring you’re also able to generally catch up on personal details and stay in touch about happenings at work.

1. Ask Questions About Hope and the Future

Questions about the future are a great way to develop a relationship because they help you learn more about what your friend wants—but also about what they value and prioritize based on the direction they want to go.

Consider asking: What would you like your career (or your life) to look like one year from now? What does success mean to you? What legacy would you like to leave behind? If it were possible to know your future, what would you (or wouldn’t you) want to know? What would you do if you knew you could not fail? If you were going to start a charity, what would it be?

2. Ask Questions About Learning and Growth

It’s also great to learn more about someone’s desires for their own growth or learning. Since development is correlated with happiness, these kinds of questions can tell you a lot about what your friend wants for themselves—and what will bring them joy.

Consider asking: If you could wake up tomorrow with one new skill or capability (something real), what would it be? What is a skill you’ve always wanted to learn or develop? What is one habit you’d like to build or strengthen in the next year? What is a small habit you started this year that has had positive effects? What is a topic you’re fascinated by and want to learn more about? What is a dream you have for your career or your personal life?

3. Ask Questions About Accomplishments

Many times, your feelings about someone else are based on how you feel about yourself when you’re with them—so asking questions that reinforce positive factors can be especially helpful in deepening a relationship and enhancing your bonds.

Consider asking: What is a choice you’ve made that you’re proud of? What is one talent or characteristic you especially like when people compliment you on or appreciate about you? What is one thing you’ve learned about yourself this year? What are three characteristics you’re especially proud of? What do you hope people say or think about you? What is something your younger self would be proud of you for?

4. Ask Questions About Regrets

Asking questions about regrets can significantly deepen a relationship, because the answers require both reflection and vulnerability. And the more you each share in a friendship, the more you’re likely to build trust and a sense of belonging based on what you’ve each been through.

Consider asking: What is some of the worst advice you’ve ever gotten? What is one thing you would like to go back and do over? What is one thing you’d like to forgive yourself for? What is your biggest career regret? What is one habit that holds you back? What is your biggest fear?

5. Ask Questions About How They Think

You can also deepen a friendship by asking questions about how your friend thinks and makes sense of things—and by comparing how you are similar and different from each other.

Consider asking: What is one rule of thumb you use to guide you? What is a reliable truism about the world or about people? What are you most grateful for, in addition to friends and family? Who inspires you and why? What brings you the most joy? What is your definition of the perfect day? What is one piece of advice you would give your younger self? If you only had a year to live, what activities would you do—or stop doing? If you didn’t do your current work/career, what would you do?

6. Ask Questions About Relationships

Since relationships are so fundamental to wellbeing, questions related to people and interactions are especially helpful. You can modify the questions based on what is most relevant based on relationship status.

Consider asking: What are the three most important characteristics you look for in a friend? What are three values you want for your family? Name three things you and your partner have in common. What is one thing you hope for you and your partner in the next year? What is one thing you’ve learned about your partner this year? What is one thing about your partner that makes you better? What are three characteristics you and your partner share in common?

7. Ask Questions About the Past

Reflecting on the past can also strengthen your bonds—because the benefit of distance gives us perspective and insight—and sharing this in a friendship can help you evolve in your understanding of each other.

Consider asking: What is one high point (or low point) from the last year? What was a favorite childhood activity that you think pointed to your career interests today? What is one thing you’d like to let go of? What is a past mistake that taught you an important lesson? What is your most treasured memory? What is your earliest memory? What is a goal that you had previously but has changed or evolved as you’ve matured?

8. Ask Questions that Are Light or Superficial

Questions about accomplishments, hopes or regrets can be intense, so it’s also wise to mix in questions that are more superficial. These kinds of questions can keep things light and get you laughing—while you’re still engaging in the process of learning more about each other.

Consider asking: What is your favorite snack to buy at a gas station or airport? What is your favorite season—and why? If you could be invisible for a day, what would you do? What is something you are superstitious about? If you could have any superpower, what would it be? What is the best gift you’ve ever given or received? If you could travel anywhere for a week, where would you go What is the perfect toast when you’re at dinner with friends or family?

Deepen Your Friendship

Good friends are good to have, and you can enhance and improve relationships through learning, sharing and exchanging information with each other—and by being vulnerable and open.

Use questions in all kinds of situations—for group discussions if you’re starting a friend group. Or to ensure you have enough to talk about if you’re reconnecting with an old friend.

Ask questions, answer questions and share together to deepen your friendship, enhance bonds and build belonging with colleagues, friends and family. You’ll contribute to your happiness and theirs as well.