Questions to ask your girlfriend

Joel Dean
Joel Dean, Founder of Joyful

You talk every day, and somehow it's all plans and memes. These 40 questions to ask your girlfriend are for going a level deeper than that. People often hold back from deep questions because they expect them to feel awkward, and yet deep conversations between strangers felt less awkward and more connecting than the people having them had predicted.1

How to use these. Choose a question you'd want to answer yourself. Ask it, then listen without fixing anything. Share your own answer after hers. If she'd rather not go there tonight, take the no as an answer.

None of these assume what women want to talk about, so use them with any girlfriend, new or long-term, and skip whichever ones don't fit her. Trick questions and "loyalty tests" aren't here, on purpose. All they measure is how well someone dodges.

A warm-up with a story in it

Light. But each one asks for a story, and a story is where you learn something about a person that a fact can't tell you.

What's the most "you" thing you did this week?

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Which smell takes you straight back to being a kid?

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What's a skill you'd learn overnight if you could?

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Tell me about the last time you laughed so hard you couldn't stop.

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Finish this: "A day I'd happily live twice is..."

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What's a movie you could quote all the way through?

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Before I knew you

She had a whole life before you showed up. Ask about it.

What were you like at fifteen, and what would that girl think of you now?

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Who was your favorite grown-up as a kid who wasn't a parent?

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Tell me about a time you moved, started over, or walked into a room where you knew no one.

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What's a decision from your early twenties that shaped where you are now?

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What did you want to be when you grew up, and what happened to that plan?

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Finish this: "Something I was sure about at eighteen that turned out wrong is..."

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What's on her plate right now

Her calendar says what she's doing. These ask how it feels.

What's taking up the most room in your head this week?

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Which part of your day do you wish were longer, and which do you wish were over faster?

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What's something you're carrying that I could take off your plate?

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When you're stressed, what do you want from me: advice, a hug, or space?

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What would make tomorrow a little easier?

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Finish this: "The thing I'm quietly proud of lately is..."

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Why deep questions feel riskier than they are

Michael Kardas, Amit Kumar and Nicholas Epley ran a series of experiments on deep and shallow conversations.1 People expected deep talks with strangers to be more awkward than they were, and felt more connected after deep talks than after shallow ones.1 The gap came from expecting others to care less about what they shared than those others did.1

One honest limit: most of these conversations were between strangers, and when people talked with close friends, family or partners, their predictions were more accurate.1 With a girlfriend, the surprise may be smaller.

The habit of holding back can still be there, months or years in, and a good question is one way past it.

What makes an answer feel heard

Jean-Philippe Laurenceau, Lisa Feldman Barrett and Paula Pietromonaco ran two diary studies in which people rated their conversations right after they happened.2 Sharing feelings predicted intimacy more than sharing facts, and feeling that the other person was responsive was part of how that sharing turned into closeness.2

The question is half the work, and the reply is the other half. Here is one answer, met three ways, in examples written for this page.

  • Fixing it: You should just ask for a meeting and sort it out.
  • Changing the subject: Mine's the same. Anyway, what do you want for dinner?
  • Asking more: What happened that made you feel that way?

The third reply asks what she feels before deciding what to do about it. It can lead somewhere like this:

"What happened? ... So he gave your idea to Sam in front of everyone. No wonder that stung. Do you want ideas, or do you just want to vent tonight?"

That example was made up too. Advice can come later. Ask first.

What feeling cared for looks like

People feel loved through different gestures. Guessing is slow; asking is quicker. The love languages page covers what that idea gets right and what the research questions.

What's something small I did that meant more to you than I realized?

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How did people show love in your family growing up?

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What's something someone did for you when you were sick that you still remember?

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Finish this: "I feel most looked after when..."

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What's a gesture that other people find romantic that does nothing for you?

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The people she loves

Her friends and family were there first, and they'll be around for the long haul too, so it pays to know who each of them is to her.

Which friend would you trust with anything, and what earned that?

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Tell me about someone in your family you'd like me to get to know better.

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What's a friendship you lost that you still think about?

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Who taught you the most about how to treat people?

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Finish this: "My friends would say the best thing about me is..."

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What she stands for

Values come out slowly. Months, sometimes. These ask about them without turning dinner into a debate.

What's a line you won't cross, even when it would be easier?

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Which cause or issue would you give a free Saturday to?

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What does a life well lived look like to you?

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Tell me about a time you stood up for someone.

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What's a rule you were raised with that you've let go of?

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Finish this: "The kind of person I'm trying to become is..."

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How we're doing

For couples already together. Pick a calm week. Never right after a fight.

What's one thing I do that makes you feel like a team?

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What's something you'd like more of from us?

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What's a conversation you've been putting off with me, and what would make it easier to start?

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When do you feel most at home with me?

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What's one memory of us you'd keep if you could only keep one?

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Finish this: "Something I want us to try this year is..."

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If a question about who she sees or where she's been keeps coming up, read trust issues or red flags in a relationship before asking it again.

Questions people ask

What are 21 questions to ask a girlfriend?

Take turns, so it stays a game. One set of 21 starts with five from the warm-up, five from "before I knew you" and five from "what she stands for". If you're already together, finish with the six in "how we're doing".

What romantic questions can I ask my girlfriend?

Romantic questions are about the two of you. Try "What's one memory of us you'd keep if you could only keep one?" or "When do you feel most at home with me?". The group "What feeling cared for looks like" has five more.

What are 20 juicy questions to ask a girl?

"Juicy" usually means personal or a little risky. The ones here that come closest: what she was like at fifteen, a friendship she lost, a line she won't cross. Personal questions land better when you answer them too, and when she can skip any of them.

What should I do if her answer upsets me?

Ask one more question before you react, such as "What do you mean by that?". If it's about you, you can say "I need a minute with that" and come back to it. The point of the question was to learn something true, and sometimes the truth stings.

More questions and guides

Sources

  1. Kardas M, Kumar A, Epley N. Overly shallow?: Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology, 2022;122(3):367-398. https://doi.org/10.1037/pspa0000281
  2. Laurenceau JP, Barrett LF, Pietromonaco PR. Intimacy as an interpersonal process: The importance of self-disclosure, partner disclosure, and perceived partner responsiveness in interpersonal exchanges. Journal of Personality and Social Psychology, 1998;74(5):1238-1251. https://doi.org/10.1037/0022-3514.74.5.1238