Questions to ask your girlfriend
39 questions for the girlfriend who has answered "how was your day" four hundred times — the ones that ask about her specifically rather than about her day, and that give her something to actually say.
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 kindness someone did for you that you've quietly copied ever since?
- What's the best thing anyone has ever given you that wasn't an object?
- What did you notice today that nobody else in the room did?
- How do you rescue a day that's going badly?
- What's the most interesting thing about your week that has nothing to do with me?
- What's missing from a normal week of yours that you keep meaning to put back in?
- What kind of tired are you at the moment — the good kind or the other one?
- What are you picky about that you'd never apologise for?
- What kind of funny do you actually like — and what kind do people keep sending you?
- What do you have genuinely good taste in?
- Which of your own opinions do you most enjoy defending?
- What have you been enjoying lately that you'd expect me to make fun of?
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's hardest for you to accept from other people — help, praise, or being told no?
- When did you last feel underestimated, and by who?
- What do you think I don't take seriously enough about you?
- What's the difference between how you are with me and how you are with your closest friend?
- What do you notice about me that I don't seem to notice about myself?
- What have you stopped explaining to people because it never lands?
- What have you been putting energy into that isn't giving much back?
- What time of day are you least aware of how you're coming across?
- What would I need to understand about the people you come from before I could properly understand you?
- Which part of your own story do you edit when you tell it to somebody new?
The ones most people never get to
Ask these when there is time and nobody has to be anywhere.
- What are you still carrying from before we met that turns up between us?
- When did you last feel genuinely unknown by someone who was supposed to know you?
- Which frightens you more — being too much for someone, or not being enough?
- What's the truest thing you could say about how this is going, including the part that flatters neither of us?
- What's the part of you you'd expect me to lose interest in first?
- What would you want me to do if you went quiet on me and couldn't explain why?
- What do you need someone to keep proving to you, however many times they've already proved it?
When something is off
The ones people skip. Skipping them is usually why the same thing keeps coming back.
- What's a rule you have about how you'll be treated, and where did it come from?
- Where are you being too patient at the moment?
- When you're disappointed in someone, do you say it or do you quietly downgrade them?
- What have you forgiven someone for that you're not sure you should have?
- What have you already decided you'd never put up with again, and what taught you that?
Where things are going
Fewer of these on purpose. A conversation that is only about the future is a planning meeting.
- What have you changed about your life recently that nobody has commented on?
- What did you learn about yourself from the last thing that went wrong?
- What are you building at the moment that isn't finished enough to talk about yet?
- What's a version of your life you'd like one year of, without giving up this one?
- What do you want out of the next few years that sounds too big to say casually?
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?
Almost all relationship advice is about handling the bad day. The measured variable is what you do with the good one. Four studies of capitalization — telling someone about a positive event — found that sharing good news raised daily positive affect and well-being above and beyond the effect of the event itself, and that the benefit depended on the response. Enthusiastic, active responses enhanced it; passive or dismissive ones did not. Couples whose partners typically responded actively reported higher intimacy and higher daily satisfaction.
Which reframes what a good question is for. Asking is the cheap half; what you do in the ten seconds after her answer is the half that was measured. A question that produces something real and is met with “nice” teaches her, correctly, that the asking was the point.
And you know her less well than the fluency suggests. In 238 dating and married couples, assumed similarity — the assumption that your partner sees things as you do — produced considerably stronger effects than accuracy, and the bias was strongest on questions about the relationship itself. The confident feeling of knowing what she would say is the bias, measured.
Gable, Reis, Impett & Asher (2004), What do you do when things go right? The intrapersonal and interpersonal benefits of sharing positive events, Journal of Personality and Social Psychology · source
Kenny & Acitelli (2001), Accuracy and bias in the perception of the partner in a close relationship, Journal of Personality and Social Psychology · source
Asking is the easy half. If she answers something real and it goes nowhere, the next question gets a shorter answer, and after three of those she has correctly learned that the questions are the point rather than the answers.
Last checked 28 August 2026.