If we’re friends offline, you likely know that I’m an expert question asker. I’m endlessly curious, and asking meaningful questions is one my few refined social skills. (I have yet to refine the art of asking questions without turning the conversation into a one-sided interrogation. . . .)

I recently put this knack for question creation to use in a post for Austin Moms by compiling a list of outside-the-box conversations starters for moms to bring to the table at their next girls’ night. The only difficult part of writing that post was limiting myself to just 25 questions, so I decided to keep the question-asking fun going with a continuation of that post right here on my own blog.

My original post was geared towards women conversing with other moms in a group setting. If you’re looking for some mom-centric discussion topics, you’ll find them there. Today’s post is filled with discussion inspiration for a few different types of conversations: questions to have with your significant other; questions you can ask your kids around the dinner table; questions to ask a close friend; and questions to ask yourself (consider answering these in a journal). Some of these are pretty intense, so make sure you “know your audience” before diving in!

Questions for Couples

1. What is your favorite memory of us together?

2. What makes us a great couple?

3. What are some areas we could improve in as a couple?

4. What is one thing I could do to make your life easier?

5. Where do you see our family in ten/twenty/thirty years?

6. When do you feel most loved by me?

7. What is the best (or worst) gift I’ve ever given you?

8. What is something we’ve never done that you would like to do together?

9. What is your favorite (or least favorite) part of our everyday life?

10. Who is a couple (real or fictional) whose relationship you admire? Why?

11. What does our relationship look like to those around us? Are we happy with this reputation?

12. What is something about your childhood that you’ve never shared with me?

13. What was the first thing that attracted you to me?

14. Are there any hobbies that we would like to try together?

15. Are we investing in relationships with other couples? If not, how can we become more intentional about finding couple-friends and cultivating those friendships?

Questions to Ask Your Kids

1. What is something I do that annoys you?

2. What is your favorite family memory?

3. How are you different from your friends? How do these differences make you feel?

4. What do you love about our house? What is something you would change?

5. If our family had a mantra, what would it be?

6. What are some family rules that you wish were in place in our home? What rules don’t you like and why?

7. What can I do to help you feel loved and supported by me?

8. Is there anything you’ve always wondered about me that you’ve been too afraid to ask?

9. What is your best advice for a sibling or friend?

10. What questions would you like to ask God?

11. What do you think your life will look like in five/ten/twenty/fifty years?

12. What is something from your childhood that you hope to do with your own kids one day?

13. What is something you are proud of?

14. What character from a movie, book, or TV show is most like you? What character do you admire the most?

15. Who is somebody that you would love to meet? What would you do if you had a chance to spend the afternoon with them?

Questions for You and Your Best Friend

1. What is your first memory of our friendship?

2. What is something great about our friendship that other people probably wouldn’t understand?

3. What is it like to be friends with me? How could I be a better friend?

4. What strengths (or weaknesses) do you see in me that I don’t see in myself?

5. How has our friendship changed over time?

6. Have I ever said or done anything that hurt you? How can I make amends?

7. What is something new that would be fun to try together?

8. What book, show, or movie have you been wanting me to experience?

9. What is your favorite fictional friendship? Why?

10. As my friend, how do you see me showing up for my family? Do I have any blind spots that need to be addressed?

Questions to Ask Yourself

1. Do I prefer being a guest in somebody else’s home, or hosting others in my own home? Why? Have I always felt this way?

2. How am I similar to my parents? How am I different? In what ways would I like to be more or less like them?

3. What is my biggest regret in life? How would I change things if I could?

4. What is a personal dream that I have never shared with anyone else?

5. What is my most vivid memory? Why does it stand out?

6. Where am I thriving in life right now? Where am I floundering?

7. What advice would I give to my younger self? What advice do I think my future self might give to me?

8. What is something I love to do that is not a part of my life right now? Do I have plans to return to it in the future?

9. When do I feel most alive? When do I feel least like myself?

10. What are ten questions I wish somebody would ask me? How would I answer?

I hope these discussion questions lead to some fruitful conversation and reflection for you and your loved ones. If you’re eager to get the question-answering going, feel free to answer any one of these questions in the Comments!