Conversation Prompts for Contemplative Communities
This is a list for my Patreon meetings — but you're welcome to use it with your group, too.
When you are a paid subscriber of this Substack, or a paid member of my Patreon community, you are invited to several Zoom calls with me and other supporters each month. Over the years we have formed a small but dedicated cadre of friends who value mystical and contemplative spirituality and who enjoy each other’s company as well.
Many groups, usually small groups, exist that can support one another in the pursuit of the contemplative life. Centering Prayer groups, group spiritual direction circles, monastic oblate communities, adult education classes at local churches — these are just a few of the kinds of gatherings that can bring together people with a shared interest in the contemplative path.
I drew up the following list of questions that I hope to work with in my own Patreon/ Substack circle of contemplative friends. Over the months to come, we’ll be exploring these questions together, hopefully fostering conversations that will be inspiring and informative. Naturally, I’d love for you to join us, if you’re not already a subscriber. But even if that’s not something you’d like to do, perhaps you would enjoy using these discussion prompts with your local community. In that spirit, I’m happy to offer these questions. With 36 prompts on this list, a weekly group can take nine months to work through them, while a group that meets once a month could use this list over a three-year period.
Happy conversing!
How did you first get interested in mysticism? What about it appealed to you? How did it capture your attention long enough to truly ignite your imagination?
Are you involved in a church or other religious organization or spiritual community? If so, did that group support your interest in mysticism, or are they indifferent to it, or even hostile to it? How do you navigate the tension between personal spirituality and religious doctrine or dogma?
Have you read one or more of the “great” mystics? If so, which one did you read first? How did you learn about that particular writer, and what impressed you about their words?
How has your understanding of mysticism changed over time (whether you’ve been interested in it for six months or 60 years)? If you had the same understanding about mysticism back then that you have today, do you think it still would have appealed to you? Why or why not?
Mysticism is often paired with contemplation. What do you think is the difference between mysticism and contemplation, and how are they related?
Has mysticism changed the way you relate to church (or other faith communities)? Has it drawn you closer to organized religion — or, drawn you away from it? Why do you think it has had the impact on you that it has?
What is your all-time favorite book on mysticism, or by a mystic? Why does that book appeal to you so much?
Have you ever read a book by a mystic, or about mysticism, that you really did not like? If so, can you reflect on why it didn’t speak to you?
Mysticism is often equated with the idea of spiritual experience, including the experience of God. Have you ever had an experience that you would identify as “mystical” — whether large or small? What was it like? Just one, or more than one? How did this experience or these experiences change you (if in fact it did)?
Do you practice the same religion that your family raised you in? And if Christian, the same denomination? Why or why not? What inspired you to change your faith identity?
Have you ever seriously explored a religion or spiritual tradition that is different from the one you grew up in? How deep did you go (did you just read up on it, or actually study it, join a community, observe the practices, etc.)? If you have in fact practiced more than one religious or spiritual tradition, how has your understanding of mysticism influenced (or been influenced by) your spiritual/religious exploration?
Do you feel conflict or tension between yourself and members of your faith community or religious institution who are not interested in mysticism? How do you manage or deal with this tension?
Did you ever join a religious community, like a monastery or a convent? Or a “lay” spiritual group, like Benedictine Oblates, Secular Franciscans, or Lay Cistercians? If so, how has that experience shaped your understanding of mysticism?
Some Christians think mysticism is dangerous. What would you say to such a person? In your experience, is their fear founded, or not? Do you have any theories as to why some religious people reject mysticism? What do you think that the contemplative community can do to allay the fears of those who reject our spirituality?
If you believe in God, has that belief changed or evolved in any way since you began to explore mysticism? How do you think mysticism has impacted your faith in, and understanding of, the Supreme Being?
If you could have a dinner party and invite five mystics from any time in history, whom would you invite? And why? What kind of questions would you want to ask your guests? What discussions would you hope would arise, especially between them? Bonus points if at least one of your invitations goes out to a non-Christian mystic.
What do you do, on a daily basis, to practice your spirituality? Are you engaged with Centering Prayer or any other contemplative practice, or the liturgy of the hours, or lectio divina, or Ignatian prayer, etc.? Why do these particular practices appeal to you?
Is there a particular contemplative practice that you don’t do, but feel drawn to trying? Alternatively, any practice that you wish you were more disciplined with, or more regularly committed to?
Does your spouse, roommate, best friend, etc. share your interest in mysticism? If not, how do you negotiate the differences in your approaches to spirituality?
If you could write a book about mysticism or about your mystical experience, what would be your core message? What would you want the title to be?
Do you see a spiritual director? Or, are you yourself a spiritual director? If so, why does spiritual direction matter to you? If not, is it something you’re interested in? Something you’d like to learn more about?
Has mysticism changed your sense of ethics or morality? Do you have a different understanding of right and wrong, or of topics like “sin” and “repentance,” than before you began to explore mysticism?
What do you think are some of the biggest issues facing humanity today? How do you think mysticism can help us to address some of these major issues?
Has mysticism changed your understanding of death and dying? How so? What do you think mysticism has taught you about this challenging topic?
Many churches are experiencing decline in their membership (and the members that are sticking around tend to be older than the average age of society). Do you think mysticism can help churches to appeal to more people? Why or why not? If you think mysticism can help churches to survive, what do you think churches should do to promote a deeper mystical spirituality?
Do you practice Centering Prayer? Why or why not? If not, do you practice any other silence-based spiritual practice, like the Jesus Prayer or walking the labyrinth. What do these practices mean to you?
Have you ever done the Spiritual Exercises of Saint Ignatius? If so, what was it like? Would you recommend it to other people? Why or why not? What was the most memorable part of the experience for you?
Have you ever walked the Camino (or a similar traditional pilgrimage)? What was it like for you? How do you think the experience changed you?
If a child or grandchild ever came up to you and asked you why mysticism is so important to you, what would you say to them? What points would you want to make during the short time that you had their attention?
There are some words associated with mysticism that many people in our culture today find difficult or controversial, words like “self-denial” or “repentance” or “humility” or “surrender” or “obedience” — and even some that the contemplative community itself tends to avoid, like “purgation” or “mortification” or “asceticism.” Do any of these words bother you? Do you think the mystics use language like this with a different understanding than society at large?
An activist in the psychedelic community once said “Mysticism is the antidote to fundamentalism.” What does that bring up for you? What is your perspective on fundamentalism? Can mysticism transform someone who is a fundamentalist? Why or why not?
What do you think is the relationship between mysticism and mental health? Do you think the study and practice of mystical spirituality can help someone dealing with anxiety, depression, OCD, PTSD, or other conditions? What do you think are some cautionary notes as we consider the possible interface between mysticism and mental health?
Do you engage in practices like yoga, tai chi, qigong, etc.? For that matter, do you fast or do anything else to include our body in your spiritual practice? What can we do to make our mystical spirituality more embodied?
Julian of Norwich famously said “As truly as God is our father, so is God our mother.” How does this land with you? Are you comfortable in seeing God as mother, or even seeing God as nonbinary or having more than one gender? If you see God as transcending gender, why do you think others find the question of God and gender to be so important? What can a mystical faith teach us about the way we talk about God?
Has mysticism impacted the way you think about sexuality and gender? Many people are squeamish talking about these topics in regard to religion and spirituality — but do you think the wisdom of the mystics has something to say about some of the issues facing our society today in regard to sex and gender?
A buzzword in the contemplative community these days is nonduality. What does that mean to you; how would you explain it to someone new to contemplative practice? Do you think nonduality is the same thing as union with God? Why or why not? Is the unitive life a nondual life? Again, why or why not?
