Questions to Ask During Courtship
Twenty questions for two people dating with a long-term commitment in view, covering daily habits, money, family patterns, children, conflict, and belief, along with guidance on how to pace the asking.
The questions
Open any question for the note
What does a normal week look like for you when nothing special is going on?
Why ask it
Courtship tends to happen on evenings and weekends, which is the least representative slice of anyone's life. The ordinary week is what you would actually be joining, and someone whose week already has no unclaimed hours will not find them later.
What are you working toward right now that has nothing to do with dating?
Why ask it
People who are building something specific describe it in detail. An answer that arrives only in terms of finding a partner is worth noticing early, because a relationship asked to carry someone's whole sense of direction usually buckles.
Who did you spend the most time around growing up, and what did you pick up from them?
Why ask it
This gets at inherited habits without asking for a family history. The interesting part is whether they can name a trait they took on deliberately, and whether they can name one they are trying not to repeat.
How did you decide you were ready to be looking for something serious?
Why ask it
Listen for whether the decision came from their own timing or from outside pressure: an age, a sibling's wedding, a lease ending. Borrowed urgency tends to produce fast commitment followed by second thoughts.
What do you want the next year to look like, and what would have to change for that to happen?
Why ask it
A one-year horizon is concrete enough to check against reality, unlike a five-year plan. The second half of the question is the useful half, because it shows whether they have connected what they want to what it would cost.
Do you get closer to someone by doing things side by side or by talking things through?
Why ask it
Mismatches here get misread as indifference for years. Someone who connects through shared activity can feel interrogated by long talks, and someone who connects through talking can read a quiet companion as withholding.
What does faith or belief look like in your life on an ordinary Tuesday, not on a holiday?
Why ask it
Stated affiliation and lived practice can be quite far apart, and the gap matters more than the label once children, in-laws, and holidays arrive. Asking about a weekday keeps the answer honest.
How did the people who raised you handle disagreement, and how much of that did you keep?
Why ask it
Most conflict styles are copied before they are chosen. Someone who says their household never argued is telling you something too: silence was the method, and it is often the method they default to under stress.
What happens to your money between one payday and the next?
Why ask it
More revealing than asking about financial goals, which everyone answers well. You are listening for whether they know their own numbers. Vagueness about where the money goes usually survives into a joint account.
How do you want to be treated when you are upset?
Why ask it
People differ on whether they want company, space, practical help, or to be left to sleep on it. Guessing wrongly during a hard week reads as neglect, and this is the one question whose answer you can act on immediately.
What do you do when you have to tell me something you know I will not want to hear?
Why ask it
Watch for whether they have ever done it. Someone who describes waiting for the right moment indefinitely is describing avoidance, and small withheld truths are what later make big ones possible.
Do you want children, and how settled is that answer?
Why ask it
The second half prevents a polite yes from passing as a decision. A firm answer either way is workable information; the situation that quietly wastes years is one person treating an open question as a settled one.
Where do you expect to be living in ten years, and how fixed is that?
Why ask it
Geography breaks up more compatible couples than temperament does. Aging parents, a family business, a professional license tied to one state: these constraints are real and are easier to hear about now than after an engagement.
What would you need from me during a stretch when things were going badly for you?
Why ask it
Asks them to picture themselves at their least impressive, which most courtship conversation is designed to avoid. An answer of nothing, or I handle it alone, predicts how much of the hard weeks you would be shut out of.
What did you learn from the way your last serious relationship ended?
Why ask it
The content matters less than the accounting. A story in which the other person supplied all the fault, or one in which they supplied all of it, both suggest the pattern has not been examined and is available to repeat.
Whose marriage or partnership do you admire, and what do they do that you would copy?
Why ask it
Asks for a working model rather than an ideal. People who can point to a specific couple and a specific practice have thought about commitment as something built. Those who cannot may be picturing a feeling instead.
Tell me about a time you were wrong about something that mattered. How did you find out?
Why ask it
The how is the test. Someone who worked it out themselves, versus someone who was told repeatedly before it landed, will handle correction from you very differently.
What have you changed your mind about in the last few years?
Why ask it
Long relationships require both people to revise views without treating it as defeat. If nothing comes to mind across several years, expect that any future disagreement will be a standoff rather than a negotiation.
What would make you decide this was not going to work between us?
Why ask it
A hard question that is fairer asked early than discovered late. It surfaces the limits they are actually holding, and their willingness to name one at all tells you how directly they will handle the difficult parts.
What have you been wanting to ask me that you have not asked yet?
Why ask it
Hands the initiative over and often produces the most useful exchange of the conversation. If they have been holding a question back, the reason they held it back is worth hearing too.
How to Use These During Courtship
Practical guidance for the conversation itself
Pacing the Conversations
One or two a week, not a list in an evening
Working through the whole set in one sitting turns courtship into an intake appointment. Pick the one you actually want to know the answer to, ask it while you are driving or walking, and let it go where it goes.
Answer it yourself first
Say your own answer before you ask, especially on money, children, and conflict. It sets the level of candor and stops the conversation feeling like an assessment they can pass or fail.
Ask the concrete version
How do you handle money is easy to answer well. What happens to your money between paydays is not. When an answer sounds like something they have said before, ask for a specific instance instead.
Return to answers later
Bring something back up two weeks on: you mentioned your brother handled it differently, how did that go. Consistency over time tells you more than any single answer, and it shows you were listening.
Reading the Answers
- Watch for the answer that describes an intention rather than a practice. I want to be better with money is not an answer to what happens to your money.
- Notice who is the subject of their stories. If every account of the past has them acted upon and never acting, you are hearing a habit, not a run of bad luck.
- Distinguish between differences of preference and differences of direction. Different holiday traditions can be negotiated. Different answers on children or on where to live cannot be split down the middle.
- Take a first no at face value on children, faith, and location. Treating it as a starting position to be worked on is how both people end up resentful.
- Pay attention to how they talk about people who are not present: an ex, a boss, a parent. It is the closest preview you get of how they will talk about you when you are not in the room.
What Not to Do
- Do not use a question as a way of announcing your own position and waiting for agreement.
- Do not raise the heaviest topics late at night, when tiredness makes ordinary differences look like incompatibility.
- Do not press for detail about a past relationship beyond what they learned. The specifics rarely help and are hard to unhear.
- Do not treat a single wrong-sounding answer as a verdict. Ask again in a month, phrased differently, before concluding anything.
- Do not skip a topic because things are going well. Money, children, and where to live are exactly the subjects a good few months tends to postpone.
When the Answers Do Not Line Up
- 1Name the difference plainly and out loud, without softening it into something smaller than it is.
- 2Separate what is negotiable from what is not, each of you privately, then compare the two lists.
- 3For anything on the non-negotiable list, decide what you would actually do if it never changed, and answer that honestly.
- 4Give it a real timeframe rather than an open one. Unresolved for now becomes unresolved for three years without either person deciding.
- 5If the difference is on children, faith practice, or location, consider talking it through with a counselor or a clergy member you both trust before an engagement rather than after one.