Deep Christian Questions to Ask Friends
Questions for small groups, discipleship pairs and long friendships built on shared faith. Twenty prompts on how someone's walk has changed in the past year, which habits they are actually keeping, honest doubt, unanswered prayer, and where they sense God asking them to move.
The questions
Open any question for the note
How has your relationship with God grown or changed in the past year?
Why ask it
A gentle opener that still needs a real answer. Watch whether they describe events or only feelings: a year summarised entirely as a season of dryness or a season of blessing usually means nobody has asked them anything specific in a while.
Which spiritual habit are you actually keeping right now, and which one have you quietly dropped?
Why ask it
Asking for the dropped one in the same breath makes honesty cheaper than performance. The habit that fell away is often the one they feel most guilt about, and naming it out loud tends to matter more than any advice you could give.
When did you last feel close to God, and what were you doing?
Why ask it
Answers are frequently not church: driving alone, holding a newborn, walking after bad news. Hearing where it actually happens for them is more useful than any general discussion of worship styles, and it tells you what to encourage.
What has God been slow about, from where you are standing?
Why ask it
This gives permission for frustration without requiring them to declare a crisis of faith. Many people carry a specific delay for years, a job, a diagnosis, a child, and have never said it plainly to a friend who would not immediately try to fix it.
What part of your faith do you find hardest to believe on a bad week?
Why ask it
Framing it around a bad week is what makes the question answerable. The honest answers are usually not obscure doctrine but the basics: that God is good, that he is paying attention, that any of it applies to them personally.
How do you handle doubt when it turns up, and who do you take it to?
Why ask it
The second half is the real question. Someone whose answer is nobody has been managing doubt in isolation, which is how it hardens. Listen for whether they have a person, or only books and podcasts.
Which passage of Scripture have you kept returning to this year, and why that one?
Why ask it
The chosen passage usually maps onto whatever they are living through, which is why the second half matters more than the first. A verse quoted with no story attached often means the answer came from memory rather than from this year.
What has changed in how you pray since you started?
Why ask it
Prayer habits shift in specific directions: shorter, less formal, more complaint, more silence, more lists. The direction of drift tells you how they are relating to God now, and it is far easier to answer than being asked to describe their prayer life.
Where are you serving now, and is it out of gladness or obligation?
Why ask it
The two words give them a way to admit burnout without resigning on the spot. Long-serving volunteers often need permission to say obligation before they can work out whether to stop, change roles, or simply rest for a season.
What is one way your faith has cost you something?
Why ask it
This separates conviction from culture. Answers range from a lost friendship or a career decision to a family estrangement. If nothing comes to mind at all, that is not an accusation, but it is worth sitting with rather than moving past quickly.
How do you tell the difference between God's leading and your own preference?
Why ask it
There is no clean answer, which is the point. Listen for whether they involve other people, wait, or look at circumstances, or whether every prompting conveniently matches what they already wanted. Both extremes are worth talking about.
Where has your church helped you this year, and where has it not?
Why ask it
Asking for both halves keeps this from becoming either a complaint session or a loyalty test. People who cannot name a single way they have been helped are frequently attending without belonging, and often have not admitted that to anyone.
Which teaching or belief have you changed your mind about?
Why ask it
Reveals whether their faith has been examined or inherited whole. What matters is not the position they landed on but whether they can describe the process: what prompted the rethink, who they talked to, what they read.
How do you live out your faith at work without it becoming a performance?
Why ask it
This is where most people spend most of their waking hours and where faith is hardest to talk about. Concrete answers involve how they handle pressure, credit and colleagues, not whether they mention church at lunch.
Who has shaped your faith most, and what did they actually do?
Why ask it
The second clause moves this from a tribute to a description. Answers are usually mundane and repeatable: someone kept showing up, someone asked a hard question, someone did not give up on them, and that is worth knowing.
What do you do with prayers that have gone unanswered for years?
Why ask it
Long silences produce different responses: some stop asking, some keep asking without expectation, some reframe the request. Whichever they describe, the fact that they still name the prayer at all tells you it has not been resolved.
Where do you find it hardest to forgive, and what have you tried?
Why ask it
Asking what they have tried keeps this from becoming a lecture on forgiveness, which they have already heard. Most people have attempted something, and hearing what did not work is more useful than telling them what should.
What sin or habit are you tired of fighting alone?
Why ask it
The word alone is doing the work: it asks about isolation rather than demanding a confession. Expect a long pause. If they name something, the only right response is to keep it, not to solve it in the next five minutes.
What is God asking of you right now that you are avoiding?
Why ask it
Most people know the answer before you finish the sentence, which is why this belongs near the end. Frequently it is a conversation, a repayment, or an apology rather than a calling, and saying it aloud is often the whole step.
How can I pray for you this month, and what would you want me to ask you about next time?
Why ask it
The second half turns a conversation into a commitment on both sides. It also gives them control over what gets revisited, which makes the whole exchange safer than an open promise to check in.
Having these conversations well
Practical guidance for the conversation itself
Before you start
Answer first, at your own cost
Depth follows whoever goes first. If you want an honest answer about a dropped habit or an unanswered prayer, give yours before asking, and make it something that does not flatter you. The level you set is the level you will get back.
Two or three questions is a full conversation
Working through a list turns a friendship into an interview. Choose two questions, ask them, then follow whatever the answers open up. The follow-up is almost always where the real subject appears.
Give the silence room
The questions about avoidance and fighting alone need a pause that will feel too long to you. Filling it with a verse or a story of your own reliably ends the conversation, even when it feels like help.
Decide what you will do with what you hear
Before asking about hidden struggles, be clear with yourself that this does not become a prayer request for the group. If a small group has never discussed confidentiality out loud, do that before anyone answers question eighteen.
What shuts these conversations down
Answering doubt with correction
When someone admits they struggle to believe God is good, a well-aimed verse lands as a correction and ends the disclosure. Ask when they started feeling that instead, and stay with the question longer than is comfortable.
Treating a confession as a project
Moving straight to accountability structures and reading recommendations tells the other person that honesty produces work. Thank them, ask what they need, and let them set the pace of anything that follows.
Spiritual language that hides the facts
Answers about seasons, walls and wilderness can be genuine or can be a way of not saying anything. Ask gently for the specifics underneath: what changed, when, and what happened just before.
Comparison, in either direction
Ranking your walk against theirs, whether you come out ahead or behind, turns the conversation competitive. Stay with their account of their own year rather than measuring it.
Where these work
- Walking or driving side by side, where nobody has to hold eye contact
- A discipleship pair that already meets regularly, taking one question per meeting
- A small group that has agreed out loud what stays in the room
- The end of a long visit rather than the start, once the news is out of the way
- Not in front of an audience, and not with someone you supervise or pastor without warning