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25 Questions To Deepen Your Friendships

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It only took about three months into my post-college, “adult” life for me to realize that grownup friendships are really stinking hard.  It took work and planning to spend time with the few people I was getting to know and it was so easy to fall into a pattern of just “catching up” and making small talk when we did see each other (like I shared about in this post about six reasons I struggled to find friends after college).

Now if you’ve followed this blog or known me for more than about five minutes, you know I’m an introvert at heart.  I love real conversations that dive deeply into the heaviest issues on our heart and nothing wears me out faster than long periods of small talk.  As such, I’m all about asking real questions that give people a chance to open up and share about how they’re doing.  It takes bravery and the risk of rejection to ask these questions, but I can think of no better way to deepen a friendship than to ask questions that clearly communicate your heart to know and love a person.

Do you wish you could deepen your friendships Asking these 25 questions can make a huge difference!

Some of these questions might feel a little cheesy at first, but if you ask them genuinely with a heart to know people, most people respond well (or give an answer that clearly shows they aren’t ready to dive deep).  I know I feel so loved when people take the time to ask me about my heart and my life, and if I feel that way, I bet other people do too!  Relationships take intentional effort to build and sounding a bit cheesy is worth the potential benefits!

With all that mind, these are some of my favorite questions to ask to get conversation going. If you’re longing to see your friendships grow and be more real, I challenge you to try to ask some of these to the people in your life!

25 Questions To Deepen Your Friendships

Questions About Life

These general, open-ended questions can open the floor and give people a chance to bring up whatever’s been on their hearts.  They can be a great way to move a conversation in a deeper direction and let people know you’re ready to listen if they do want to share!

  1. How have things been going lately?
  2. I remember you mentioning ______.  Any updates with that?
  3. How have you been feeling about _________?
  4. What’s been a high or low from the last few weeks?
  5. Is there anything you’re looking forward to or nervous about in the next few weeks?

Questions About Marriage

How we’re doing in our marriages has such a huge impact on how we’re doing in general.  Sometimes people are hesitant to talk about marriage because they don’t want to break their partner’s trust or open up about how hard it is, but I’m a big believer that the hard parts of marriage need to be talked about.  Asking questions like these opens up the floor for people to share about the relationship that’s such a huge part of their daily lives (to whatever extent they feel comfortable. You can ask similar, slightly-modified questions for friends who are dating or single as well!

  1. What’s been the best part about marriage and the hardest thing about marriage?
  2. How has marriage surprised you or been different than what you expected?
  3. Have there been any themes that have come up over and over in your hard conversations?
  4. What are some of your dreams for your marriage?
  5. What are the two of you excited or nervous for about the future?

Questions About Work

As adults, we spend so much of our day at our jobs.  Asking people questions about work is asking them questions about a huge part of their lives and can provide a lot of insight into their hearts.

  1. What are your days like at work?
  2. What are the people you work with like?
  3. How do you like the work you’re doing?
  4. What would be your dream job if you could do anything?
  5. How do you feel like you’re growing or changing because of this job?

Questions About Faith

These ones can feel so strange to ask at first, but I’ve had so many good conversations when I follow God’s leading and am brave enough to ask these questions.  Follow your gut on these ones.  If the timing is right, they can lead to deep, vulnerable conversations.

  1. How have things been with faith lately?
  2. Where do you feel like God is in the midst of _________?
  3. How do you think God feels about ______ situation?
  4. Are you disappointed with God?
  5. What have you learned about God in _______ situation?

Questions About Support

When we have real conversations, sometimes the hardest part is knowing how to end it.  I’m learning to ask these practical questions to give people a chance to ask for support.

  1. How can I support and encourage you in this?
  2. Do you feel like you’ve had anyone support you or encourage you in the midst of this?
  3. What would make you feel loved and supported over the next few weeks?
  4. How can I pray specifically for ________?
  5. How do you want me to follow up with you about this?

Building and growing relationships is sometimes as simple as mustering the courage to ask a real question.  And in the years of early adulthood when so many big life transitions come and go, having real friendships where you feel safe sharing the real and hard parts of life is so crucial.

What are some of your favorite questions to help conversation flow? 

You might also like…

Do you ever feel like you're a "fake" grownup and eventually everyone will realize it? You're not alone, my friend.Finding friends after college is hard and these six things I did made it even harder. Check out this post to read how I overcame these obstacles!Seven Practical Tips To Grow And Deepen Adult Friendships - Check out these tips for practical steps to help your grownup friendships grow!

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Comments

  2. LOVE this list! As an introvert too, I have deep desire to develop strong, close friendships but it’s hard to get there. These questions help get it in focus. Thank you!

  3. These are great questions to make a friendship flourish. I recently finished university and moved to a new city by myself for work. I never realized how hard it would be to start new friendships (I work with people all older than I am). Thank you for the tips 🙂

  8. YES. You know that I adore your posts about friendship as I am really struggling to find friends in this season of being a newlywed. We have joined a married Bible Study and am finding it hard to connect with the people in the group. But these questions are going to help so much! You’re so wise, Lauren.

    • Aww Annie your comments are always so sweet and encouraging! I’m so glad you guys joined that study. I’m excited to hear more about it! These questions could definitely be good to sneak in or even use as an opener for the whole group!
      Lauren recently posted…Easy Initials Pennant TutorialMy Profile

  12. This is a great list! One of the PR tips I learned in Grad school was to remember personal details about people with whom you have professional relationships. I always try to do this and, as it turns out, you catch more flies with honey and I’m always able to get things accomplished with the help of others. I know that sounds a little shallow, but I’m trying to say that things like these help strengthen even professional relationships. People like to know you care.
    Nicole recently posted…Day 93: Kona’s Second Round of InjectionsMy Profile

  17. I love love love conversations involving questions like these. As a Comm Arts teacher, these questions are engrained in me 🙂 Can’t wait to get together soon and talk about some of these. Thanks for sharing the reminder to be purposeful with those around us!
    Kelsie recently posted…A Moment with Abby: Trusting God’s PlanMy Profile

  18. great thought provoking questions that truly can open up discussions that create intimacy.:) It is amazing once that door is opened it remains open so much easier:)

  20. LOVE this list, Lauren! My closest friend and I haven’t lived in the same town for almost five years. When we would get together we would spend most of the time catching up on the basics. But this year we’ve started being more intentional and digging deeper, and it has been such an incredible blessing. I’m pinning your list to refer back to as I hopefully make more adult friends.

    Thanks for sharing your heart on friendship with us. You are blessing! 🙂

  21. Ahhhh THIS -> “I remember you mentioning ______. Any updates with that?”

    I love when people ask something similar to that! It makes me feel so good when a friend (or family member) recalls something I’ve mentioned in the past and asks me about it. To me, it shows that they listen to and care about me. That’s a great one to include.
    Ashley LaMar recently posted…One More Day: A Book ReviewMy Profile

  22. You’re so right. Maintaining adult relationships and friendships take work. Everyone says life gets in the way but we should consider these friendships an important part of our lives. I love these open ended questions about certain topics. It makes people give you more than a one word answer! Way to get the conversations started.

  24. As a fellow introvert, I love deep conversations but I have such a hard time asking good questions to actually get there. I hate the old standby “How’s work?” — so many of us use it without ever giving or getting a real answer. So I particularly like your work questions to get the conversation going!

  26. This was such a great post! Helpful, actionable wisdom that affirmed we are not alone in finding adult friendships difficult. Thank you! I shared this with my blog readers on Facebook today and home they find it as inspiring as I did! <3

    • Thanks, Erica! I completely agree with you and remember getting so frustrated with that in college. Those deep conversations are so essential!

  29. I love this list! I know you said you felt some of them were “cheesy,” and I know what you mean, but these questions are so important and often overlooked. Something you mentioned in terms of encouragement and support is what I’ve been trying to do since Brittany wrote about it months ago: How can I support you? Instead of trying to chime in always or offer advice, I always ask them this. Wonderful post, Lauren.
    Lindsay recently posted…The Importance of Accepting ComplimentsMy Profile