50 questions

Questions to ask your partner about the future

Couples rarely break up over a disagreement about the future. They break up over having assumed agreement for several years and finding out late. The assumption is comfortable precisely because it is never tested, and the cost of testing it rises every month.

These questions are deliberately concrete. "Do you want a good life" produces agreement and no information. "How near do you want to live to your mother" produces an answer that can be planned around. Wherever possible the questions below ask for a number, a place or a date.

A warning worth taking seriously: do not treat a single answer as a contract. What people want at thirty is not always what they want at thirty-five, and the point of asking is to know where you both are now, not to hold each other to a position later.

The shape of the life

Start wide, then get specific. The specificity is where the disagreements actually surface.

1What does an ordinary good week look like to you in five years?
2What do you want more of in your life than you have now?
3What are you willing to be worse off for?
4What does success look like to you when nobody is watching?
5What would make you feel you had wasted this decade?
6How ambitious are you, really?
7What kind of life would bore you?
8What do you want your forties to be about?
9What would you like to be doing at seventy?
10What is the life you would quietly regret not having?

Where you live

Frequently assumed, rarely agreed. Worth resolving explicitly, because it constrains almost everything else.

1Where do you want to be living in ten years, specifically?
2How strongly do you feel about that, on a scale?
3Would you move country for the right opportunity?
4How close do you want to be to your family?
5How close do you want to be to mine?
6City, town or somewhere with nothing around it?
7Would you rather own somewhere small or rent somewhere good?
8How much would you sacrifice for a shorter commute?
9What would make you refuse to move?
10If I got an offer somewhere you did not want to live, what happens?

Money

The most avoided subject and the most predictive one. These are practical rather than philosophical on purpose.

1What does having enough money mean to you, as a number or a feeling?
2What are you saving for at the moment?
3How do you want us to handle joint and separate money?
4What do you think is worth spending on without guilt?
5What makes you anxious about money?
6How much debt would you be comfortable with?
7What would you do if one of us earned much more than the other?
8How do you feel about supporting family financially?
9What would you want us to do with a windfall?
10How much do you want to be working at fifty?

Children and family

Best asked early and revisited honestly. The failure here is assuming a maybe will resolve in your favour.

1Do you want children, and how certain are you?
2If yes, when, roughly?
3How many, and how firmly do you hold that?
4What would you want to do differently from how you were raised?
5How would we split the work of it, in practice?
6What would we do if we could not have them?
7How do you feel about adoption?
8What role do you want our parents to have?
9What would you want a child of ours to grow up believing?
10What is your honest fear about becoming a parent?

Us, specifically

The future of the relationship itself, rather than of the life around it.

1What do you want us to have done together in the next year?
2How do you feel about marriage, and what would it mean to you?
3What would you want our tenth anniversary to look like?
4What do you want us to still be doing every week in twenty years?
5What would you want me to promise you?
6What do you need from me to feel secure about the future?
7What are you afraid will change about us?
8What would you want us to protect no matter what?
9What is something we should decide this year rather than next?
10What are we both assuming that we have never actually said out loud?

Keep asking without having to remember

The hard part of this is not the questions, it is the habit. Most couples read a list like this, have one good conversation, and never open it again. HeartTap exists mainly to remove that failure: it sends one question at a time to both of you, and hides each answer until you have both written yours, so neither of you drifts toward agreeing with the other.

Frequently asked questions

When should couples talk about the future?

Earlier and more often than most do. The cost of an inconvenient answer rises with attachment, so a question that is casual in month three is heavy in year three and devastating in year six. Asking early is not pressure, it is the cheapest possible version of the conversation.

What if we want different things?

Then you have learned something extremely useful at the lowest available price. Some differences are negotiable, such as timing and location. Some are not, and children is the clearest example: there is no compromise position between having them and not. Knowing which kind you are facing is more important than resolving it immediately.

How do I bring up the future without sounding like an ultimatum?

Ask about their picture rather than about your shared one, and ask out of curiosity rather than for a commitment. "Where do you want to be living in ten years" is a question about them. "Are we going to move in together or not" is a demand wearing a question mark, and it gets answered as one.

Should we write these answers down?

It helps, mostly because it stops the second person adjusting to the first. Answering separately and comparing surfaces genuine difference that a live conversation smooths over. HeartTap does this by default, hiding both answers until each of you has written yours.

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