60 questions
Questions to ask your boyfriend
Most lists of questions to ask your boyfriend fail in the same way: they are written to be scrolled, not asked. Fifty variations on "what is your favourite colour" produce a pleasant two minutes and nothing you did not already know. The questions worth asking are the ones where you genuinely cannot predict the answer.
This list is grouped by what the moment can hold. Some of these work over text on a Tuesday afternoon. Some need a long drive, or the particular honesty that arrives after eleven at night. Asking a heavy question at the wrong moment usually gets you a shrug, which then reads as him being closed off when really it was just badly timed.
A note on how men in particular tend to answer: many will give you a short answer first and the real one about ninety seconds later, if you leave the silence alone. The temptation is to fill the pause or move to the next question. Do not. The second answer is the one you asked for.
Light questions that still tell you something
Good over text or while cooking. They look casual and still return something you can build on.
- 1What is the best thing that happened to you today that you would not have mentioned?
- 2What is something you are irrationally good at?
- 3What did you want to be when you were nine, and what happened to that?
- 4What is the last thing that genuinely made you laugh out loud?
- 5What is a small thing that instantly improves your mood?
- 6What is your most-used app, and are you happy about that?
- 7What is something everyone seems to enjoy that you find overrated?
- 8What would you do first if you had a free Saturday and no obligations?
- 9What song do you know every word of?
- 10What is the pettiest thing you have ever held a grudge about?
- 11What food would you eat every day if it had no consequences?
- 12What is the best money you have ever spent?
Questions about who he is
These get at character rather than preference. Most of them are things he will not have been asked before, which is the point.
- 1What do you think you are underestimated for?
- 2What is a compliment you got once that you still think about?
- 3When do you feel most confident?
- 4What is something you changed your mind about in the last few years?
- 5What do you do when nobody is watching that you are quietly proud of?
- 6What is the hardest thing about being you that people do not see?
- 7Who do you become around your oldest friends?
- 8What is a rule you live by that you have never explained to anyone?
- 9What kind of tired are you most often?
- 10What do you think people get wrong about you on first meeting?
- 11What is something you are working on about yourself?
- 12When did you last surprise yourself?
Questions about us
Ask these when things are calm rather than when something is already wrong. They land much better as curiosity than as evidence gathering.
- 1What was going through your head the first time we met?
- 2What is something I do that makes you feel looked after?
- 3When do you feel closest to me?
- 4What do you wish I asked you about more often?
- 5What is something you want to do together that you have not suggested?
- 6How do you like to be comforted when you have had a bad day?
- 7What do you need from me when you go quiet?
- 8What is a way I could make your week easier that I am not doing?
- 9What do you think is our best quality as a pair?
- 10Is there anything you have been meaning to tell me?
- 11What would you like more of from me, and what would you like less of?
- 12What do you think we are good at that other couples struggle with?
Questions about the future
These are the ones that decide whether you are walking in the same direction. Ask them early enough that the answers can still change something.
- 1What does your ideal ordinary week look like in five years?
- 2Where do you want to be living, and how strongly do you feel about it?
- 3What do you want your work to give you besides money?
- 4How do you feel about children, honestly rather than diplomatically?
- 5What is a goal you have that you have not told anyone about?
- 6What would you want us to have done together by this time next year?
- 7What does financial security look like to you specifically?
- 8How close do you want to live to your family?
- 9What would you regret not trying?
- 10What kind of older person do you want to be?
- 11What would make you say a year had been a good one?
- 12What are you willing to give up for the life you want, and what are you not?
Serious questions for when there is time
Save these for a night with no alarm set in the morning. One of them is usually enough for a whole evening.
- 1What is the hardest thing you have been through, and who were you afterwards?
- 2What do you carry that you have never put down?
- 3What are you afraid I will stop doing?
- 4What is something you have forgiven someone for that you should not have?
- 5What is something you have not forgiven that you probably should?
- 6When did you last cry, and what about?
- 7What is the loneliest period of your life so far?
- 8What do you think your father got wrong, and are you repeating it?
- 9What would you want said about you at the end?
- 10What do you want that you feel you are not allowed to want?
- 11What is a truth about you that you think would change how I see you?
- 12What are you hoping I will ask you?
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
What are good questions to ask your boyfriend over text?
Stick to the light section. Text is bad at nuance and worse at silence, so a heavy question over text usually gets a short answer that reads as dismissive when it was really just the wrong medium. Save anything about fear, family or the future for a conversation where you can both hear tone.
How many questions should I ask in one go?
One, usually. Three at most. A list worked through in order turns into an interview, and people answer interviews carefully rather than honestly. Pick the one you are actually curious about, ask it, and then follow it wherever it goes, which is where the real conversation lives.
What if he gives short answers?
Wait longer than feels comfortable before you speak again. A lot of people, and a lot of men in particular, answer briefly first and then properly if the silence is left alone. If he is genuinely not in the mood, drop it entirely rather than rephrasing, and come back another day.
What questions should I ask a new boyfriend?
The light section and the questions about who he is. Both are honest without asking for exposure he has no reason to offer yet. The relationship and future sections work better once you have enough shared history that the answers carry real weight.
One question a day, answered together
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