Skip to content
HeartTap

60 questions

Questions to ask your girlfriend

The point of asking your girlfriend a question is not to gather information. It is to show that you are still curious, which is a different and more valuable signal. Long relationships tend to fail slowly, through the accumulated sense of being known about rather than known, and curiosity is the cheapest available fix.

These are grouped by weight. The first sections work anywhere, including in a queue or over dinner. The last section is for a night with nothing scheduled afterwards. Asking a serious question in a stolen ten minutes tends to produce a careful answer, because there is not enough room for a real one.

One thing that helps more than the wording of any single question: ask a follow-up. Most people give a headline first and the substance only if you seem to want it. "Why that one?" is doing more work than any clever question on this page.

Playful questions

These do not pretend to be profound. They are for the ordinary evenings, which are most of them.

  1. 1What is the most unhinged thing in your search history right now?
  2. 2What is a small luxury you would never give up?
  3. 3What compliment do you never get but would like to?
  4. 4What would your reality show be called?
  5. 5What is something you pretend to like more than you do?
  6. 6What is the best terrible film you have seen?
  7. 7What did you think was normal as a kid that definitely was not?
  8. 8What is your most controversial food opinion?
  9. 9If you had to give a fifteen-minute talk with no notes, what would it be about?
  10. 10What is the pettiest hill you would die on?
  11. 11What thing do you own that you would grab first in a fire?
  12. 12What is the last thing that genuinely delighted you?

Questions about how she thinks

A step past preferences. These ask her to explain something rather than just report it, which is where people become interesting.

  1. 1What do you think you are unusually good at reading in people?
  2. 2What is a belief you hold that you cannot fully justify?
  3. 3When do you trust your gut, and when do you override it?
  4. 4What is the best decision you have made against advice?
  5. 5What do you find genuinely difficult that other people seem to find easy?
  6. 6What did you have to unlearn?
  7. 7What kind of person do you find yourself drawn to as a friend?
  8. 8What do you think you will care much less about in ten years?
  9. 9What advice do you give that you do not follow?
  10. 10When do you feel most competent?
  11. 11What is something you have changed your mind about recently?
  12. 12What is a question you wish people asked you?

Questions about us

Ask these out of interest, not audit. Timing matters more here than anywhere else on the page.

  1. 1What did you think of me before you liked me?
  2. 2When do you feel most secure with me?
  3. 3What is something I do that makes you feel seen?
  4. 4What do you wish I understood about you without you having to say it?
  5. 5What is something you have wanted to ask me for?
  6. 6How do you want to be treated when you are upset with me?
  7. 7What is a small thing I could do this week that would matter?
  8. 8What do you think I misread about you?
  9. 9What is your favourite ordinary thing we do together?
  10. 10What would you want us to be better at?
  11. 11When did you last feel proud of us?
  12. 12What do you want more of from me?

Questions about the future

Worth asking before assumptions harden. Two people can agree on every value and still want different lives.

  1. 1What does a good ordinary Tuesday look like in five years?
  2. 2What do you want your life to have room for that it does not now?
  3. 3How do you feel about children, and has that changed?
  4. 4What kind of home do you want, and how much does it matter?
  5. 5What is a career version of you that you are curious about?
  6. 6How near do you want to be to your family?
  7. 7What would you want us to have done by the end of next year?
  8. 8What are you saving toward, really?
  9. 9What would you want to try if failing were free?
  10. 10How do you want to feel about money?
  11. 11What does a good old age look like to you?
  12. 12What is the life you would be quietly disappointed not to have?

Serious questions

For a night with no alarm the next morning. Ask one, not five.

  1. 1What is the hardest year you have lived through?
  2. 2What did you need then that you did not get?
  3. 3What do you think you are still carrying?
  4. 4What are you most afraid of in relationships generally?
  5. 5What is a fear about us you have not said aloud?
  6. 6What do you find hardest to forgive?
  7. 7When have you felt most alone?
  8. 8What is something about your family you have never explained to me?
  9. 9What part of yourself do you keep out of sight?
  10. 10What would you want me to do if you were not coping and would not say so?
  11. 11What do you want that you feel guilty for wanting?
  12. 12What would you want me to know if we only had this conversation?

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.

Related question sets

Questions to ask your boyfriend

Sixty questions sorted by mood, from the ones that work over text to the ones that need a quiet evening.

Deep questions to ask your partner

Sixty questions that go past the surface, sorted from gentle to genuinely searching.

All question topics →

Frequently asked questions

What are good questions to ask your girlfriend to get to know her better?

The section on how she thinks is the most productive one, because it asks her to explain rather than report. Preferences tell you very little; reasoning tells you a lot. Ask why after the answer and you will learn more from one question than from a list of twenty.

How do I ask questions without it feeling like an interrogation?

Answer them yourself too, and go first when the question is a hard one. A question you would not answer is a demand rather than a question. Keep it to one at a time, and let the conversation wander away from the list, which is usually where the good part is.

What if the answer upsets me?

Say that it did, calmly, and stay in the conversation. The worst outcome is not a difficult answer, it is teaching her that honest answers cost her something, because she will give you fewer of them from then on. Thank her for the honesty even when you dislike the content, and take the actual disagreement up when you are not raw.

How often should we do this?

Regularly and lightly beats rarely and intensely. A single question a few times a week keeps curiosity alive without turning into an event. Apps that deliver one question a day, HeartTap included, exist mostly to remove the step of remembering to ask.

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.

Download on theApp StoreGet it onGoogle Play