Deep questions to ask your partner
A deep question is one whose answer tells you something about who your partner is rather than what they did — here are 41, ordered by how much they cost to answer, from the ones you can ask over dinner to the ones that need a free evening.
Easy ones, to start
Nobody opens with the hard question. These are the ones you can ask with the plates still on the table, and they still tell you something.
- What's a small thing I do that you'd miss if I stopped doing it?
- What was the smallest thing that made you feel loved this month?
- What did I do this week that made your day easier?
- If we had a completely free Saturday next month, what's your actual first choice — not the easy suggestion?
- Which room in our place do you actually like being in, and what do you do in there?
- What's the best hour of your average day right now?
- What's something you nearly bought for yourself lately and talked yourself out of?
- What did you think about on the drive home this week that you never got round to saying?
- What's the last thing you laughed at on your own that you never told me about?
- Which version of me do you feel closest to — morning me, late-night me, holiday me, or working me?
Questions that actually go somewhere
The middle rung. Still safe, but the answer is about who someone is rather than what they did, which is the whole difference.
- What do you need from me in the first ten minutes after you walk in the door?
- What do you think I'm most afraid of right now?
- What's the last thing you decided not to tell me, and what were you weighing up?
- What have you wanted to ask me for and haven't, because it felt like too much to ask?
- When did you most feel like we were a team this year? Give me the actual day.
- How do you know when I'm pretending to be fine?
- What part of your own life has got smaller since we've been together?
- What am I like to live with when I'm stressed? Describe me from the outside.
- Which of your parents do you catch yourself being with me?
- What decision did we make together that you went along with more than you agreed with?
- What do you do for me that you wish I noticed more often?
The ones most people never get to
Ask these when there is time and nobody has to be anywhere.
- Say three true sentences that start with 'we are both' — about the two of us, right now, in this room.
- Tell me something you like about me that you'd be embarrassed to say in front of anyone else.
- What need of yours have you quietly decided I'm never going to meet?
- What would you need to see from me to keep choosing this for another ten years?
- What do you think you take from me that you don't give back?
- What's the part of yourself you still keep out of my sight?
- What's the closest you've come to leaving, and what stopped you?
When something is off
The ones people skip. Skipping them is usually why the same thing keeps coming back.
- When did you last feel lonely with me in the room?
- Which of our arguments do you think we're never going to solve, and how do you want us to live with it?
- What subject do you steer us away from?
- What have you forgiven me for without ever telling me you were upset?
- What have you been resenting me for that you've never said out loud?
- If I were gone tomorrow, what would you most regret never having told me?
- What's the moment in our relationship you'd take back if you could?
Where things are going
Fewer of these on purpose. A conversation that is only about the future is a planning meeting.
- What have you gotten better at since we met that has nothing to do with me?
- Picture an ordinary Tuesday night a year from now. What are the two of us doing?
- What are you looking forward to in the next three months that you haven't mentioned to me?
- How have I changed in the last two years in a way you're still adjusting to?
- What's changed about what you want from your work in the last five years that I might have missed?
- What's the one thing you most want to be different about the next year of us?
Some questions are easier to answer when neither of you chose them.
That’s why we made them into a wheel. Spin it — this one is loaded with the questions on this page.
Press spin. You do not get to pick.
Does any of this actually work?
Yes — but not for the reason the internet gives, and the difference decides which questions belong on a list like this. Arthur Aron’s 1997 experiment is the one everybody cites: strangers who worked through a set of increasingly personal questions reported significantly greater closeness afterwards than pairs who spent the same forty-five minutes on small talk.
What almost nobody quotes is what the small-talk group was actually doing. The control condition was not a list of closed questions. It was open, elaborative and pleasant — “Describe the last time you went to the zoo” — structurally the same shape as the 36. It still produced markedly less closeness: 4.06 against 3.25, roughly 0.88 of a standard deviation. So being open-ended is not the active ingredient. Self-revelation is. That is the test every question below has to pass: after the answer, do you know something about who they are, or only about something that happened to them?
The second finding is that you will misjudge the cost of asking. Across five experiments, people overestimated how awkward a deeper conversation would feel and underestimated how connected it would leave them — and the gap was widest for the deep questions, not the shallow ones. Which is the wrong way round for anyone deciding how far down a page like this to go.
And the answer is only half of it. In a study where one person in each of 199 online-chat pairs was privately told to ask at least nine questions and the other to ask at most four, partners liked the high askers more — with follow-up questions doing most of the work. The askers themselves did not predict this. Asking the question is easy; the second question is what the page is really for.
Aron, Melinat, Aron, Vallone & Bator (1997), The Experimental Generation of Interpersonal Closeness, Personality and Social Psychology Bulletin · source
Kardas, Kumar & Epley (2022), Overly shallow?: Miscalibrated expectations create a barrier to deeper conversation, Journal of Personality and Social Psychology · source
Huang, Yeomans, Brooks, Minson & Gino (2017), It doesn’t hurt to ask: Question-asking increases liking, Journal of Personality and Social Psychology · source
Depth is not a difficulty setting. A question that asks for more than the person is ready to give does not produce intimacy, it produces a polite deflection — and if the last three of these land badly, that is information about the timing, not about the relationship.
Last checked 28 August 2026.