60 questions

Deep questions to ask your partner

A deep question is not just a heavy one. The questions that actually change how two people see each other tend to be specific rather than grand, and they ask for something the other person has not already told a hundred times at parties. "What is your biggest fear" gets you an answer someone has rehearsed. "What is something you are afraid I will find out about you" gets you the truth, or at least an interesting silence.

The list below is ordered by how much it asks of you. The early sections are safe for a long drive or a quiet evening a few months in. The later ones assume a relationship with enough trust that an honest answer will not be used against you later. Start where you actually are, not where you think you should be.

One practical suggestion: answer at the same time rather than taking turns. When one person goes first, the second answer bends toward the first, and you end up agreeing more than you really do. Writing your answers separately and revealing them together is a small mechanic that changes what people are willing to say.

Questions about how you see each other

A gentle place to start. These ask for observation rather than confession, so they are easy to answer honestly without feeling exposed.

1What do you think I am better at than I give myself credit for?
2When did you first realise you had feelings for me, and what gave it away?
3What is something small I do that you would miss if I stopped?
4How do you think I have changed since we met?
5What do you think I worry about that I never say out loud?
6If someone asked you to describe me in one sentence, what would you say?
7What is a version of me you have never met that you would like to?
8When do you find me hardest to read?
9What is something I believe about myself that you think is wrong?
10What do you notice about me that you think nobody else does?
11Which of my habits did you find odd at first and now find comforting?
12What do you think I am secretly proud of?

Questions about your history

People are largely explained by things that happened before you met them. These questions go looking for that without asking anyone to relive it.

1What is a moment from your childhood that still shapes how you act now?
2Which of your parents do you take after in ways you would rather not?
3What did you need at fifteen that nobody gave you?
4What is something you were praised for so often that it became a trap?
5Who taught you what love was supposed to look like, and were they right?
6What was the first thing that ever really disappointed you?
7What is a friendship you lost that you still think about?
8What were you like before life sanded the corners off?
9What is something your family treated as normal that you later realised was not?
10Which past version of yourself do you feel protective of?
11What is the kindest thing anyone has ever done for you?
12What did you once want desperately that you are glad you did not get?

Questions about the relationship itself

These are the ones most couples skip, on the theory that not naming a thing keeps it from being real. Naming it is usually the cheaper option.

1What do you need from me that you have never actually asked for?
2When was the last time you felt lonely while we were in the same room?
3What is something we disagree about that we have quietly stopped discussing?
4What would make you feel more chosen than you do now?
5Is there a conversation you have been avoiding with me?
6What do you think we are avoiding as a couple?
7When do you feel most like a team with me, and when do you feel least like one?
8What is a compromise you made that still stings a bit?
9How would you know if I were unhappy? Would you know?
10What is something I do during an argument that makes it worse?
11What would you want me to do differently the next time you are upset?
12What are we better at now than we were a year ago?

Questions about fear and failure

Harder ground. Ask these when there is time to sit with the answers, and not on the way to somewhere.

1What are you most afraid of losing that is not a person?
2What failure are you still carrying that you have never fully admitted?
3What do you think you would do if I were not here?
4What is a fear about us that you have never said out loud?
5What is something you are ashamed of that you think I would understand?
6When have you felt like a fraud?
7What is the loneliest you have ever been?
8What would you change about how you handled the hardest year of your life?
9What do you think you are running from?
10What is a decision you made that you would make differently now?
11What would you need to forgive yourself for?
12What is the thing you most hope I never find out, and could you tell me anyway?

Questions about meaning and the long view

These pull the camera back. They work well late at night, and surprisingly well on a long walk when neither of you has to hold eye contact.

1What do you want your life to have been about?
2What would make you feel like you had wasted your twenties, or your thirties?
3What do you believe now that you would have argued with ten years ago?
4What does a good day look like to you when nothing special happens?
5What would you do with a year that nobody would ever know about?
6What do you want to be remembered for by five people, not by everybody?
7What is something you believe that most people around you do not?
8When do you feel most like yourself?
9What are you postponing that you should not be?
10What would you regret not having said?
11What do you think we are building together, in plain words?
12If we are still here in thirty years, what do you hope we still do every week?

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 is the right time to ask deep questions in a relationship?

Earlier than most people think, but matched to the trust you actually have. The first two sections here suit a relationship of a few months. The sections on fear and on the relationship itself assume enough trust that an honest answer will not be held against the person later. The wrong time is mid-argument, or when one of you is exhausted and wants the day to end.

What if my partner does not want to answer?

Let it go and mean it. A question that becomes an obligation stops being a question. Say that they can come back to it, then actually drop it. Most people who deflect a deep question return to it a day or two later, once they have had time to work out what they think, and that answer is usually better than the one you would have extracted.

How do I answer a deep question honestly without starting a fight?

Answer about yourself rather than about them. "I feel distant when evenings get busy" is a fact about you and can be discussed. "You never make time for me" is a charge and will be defended against. The content can be identical, but only one of the two leaves room for a reply.

Is it better to answer at the same time or take turns?

At the same time, when you can. Whoever answers second is influenced by the first answer, usually toward agreement, which quietly removes the point of asking. Writing your answers separately and revealing them together avoids that. HeartTap has this built in: turn on Reveal after partner answer and neither of you sees the other’s response until both are written.

One question a day, answered together

HeartTap delivers a question at a time from a library of over 2000, and keeps both answers hidden until you have each written yours. Free on iPhone and Android.

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