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Questions to Ask Your Girlfriend

Deepen your bond and make her feel heard. These questions help you explore her thoughts, dreams, and favorite memories.

Being asked a good question is a form of attention, and attention is most of what these are for. Ask one, listen to the whole answer, and ask a follow-up about the part she got animated about rather than moving to the next item on the list. The sections cover what she loves, how she wants to be cared for, and what she is moving toward.

What she loves

Start light. These are enjoyable to answer and they show you what she lights up about, which tells you where the follow-up questions are.

  • 1What is a song that always puts you in an amazing mood?
  • 2What was your favorite family tradition growing up?
  • 3What is a topic you could talk about for hours without getting tired?
  • 4What is a secret talent or weird quirk you have that not many people know about?
  • 5If you could design our dream living room, what would it look like?
  • 6What is something that instantly reduces your stress after a long day?
  • 7What is a place you have been that you would go back to tomorrow?
  • 8What is something you loved as a kid that you would still enjoy now?
  • 9What is a small purchase that improved your life more than it should have?
  • 10What is something you find beautiful that most people walk past?
  • 11What is your favorite way to spend a morning with no plans?
  • 12What is something you would happily learn about for a year?

How she feels cared for

The section that changes how you show up. These answers are specific and actionable, and most of them are things she has never been asked directly.

  • 13What is a small gesture that always makes you feel loved and cherished?
  • 14What was the moment you felt safest with me?
  • 15What is your favorite compliment to receive?
  • 16When do you feel most beautiful and confident?
  • 17What is your love language, and how can I speak it better for you?
  • 18What is the sweetest thing someone has ever done for you?
  • 19What does emotional intimacy mean to you?
  • 20What is something you wish more people understood about you?
  • 21What do you need from me on a bad day that you have never spelled out?
  • 22What is a kind of help that actually helps, rather than adding pressure?
  • 23When do you most want to be left alone, and how would I know?
  • 24What is something I do that you have never told me you love?

Where she is headed

Forward-looking. These give you something to support rather than just something to know.

  • 25What is a dream you've had for years that you haven't started working on yet?
  • 26What is something about the future that excites you the most?
  • 27How have your priorities in life changed over the last three years?
  • 28What is a memory of us that always brings a smile to your face?
  • 29What is your favorite date we've ever been on and why?
  • 30What is one thing I do that makes you laugh the hardest?
  • 31What is something you want to be true about your life in five years?
  • 32What is a version of yourself you are working toward?
  • 33What would you do with a completely free year?
  • 34What is something you want us to do while we still can?
  • 35What is a goal of yours I could actually help with?
  • 36What is something you want to stop putting off?

Questions about these questions

What is the best time to ask these?
When neither of you is tired and there is no clock running. A walk, a long drive, or a dinner with nowhere to be afterwards. Asking a thoughtful question ten minutes before bed usually gets a tired answer.
How do I follow up without pushing?
Ask about the part of the answer she got animated about, not the part you found most interesting. Following her energy is the difference between a conversation and an inquiry.
What if we have been together for years?
The middle section is written for exactly that. Long-term couples usually know each other's history well and have stopped asking about the present — what she needs on a bad day is not a fixed fact.

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