150 Questions to Ask Your Girlfriend: Deep, Fun & Flirty

Asking your girlfriend good questions is one of the easiest ways to feel close again, whether you’ve been together for three weeks or three years. The problem: most guys run out of ideas after “How was your day?”. Below are 150 questions, sorted by mood, so you can pick what fits the moment.

Before you start, one rule: this is a conversation, not an interview. Ask one question, listen, ask a follow-up, share your own answer. Three good questions in an evening beat thirty quick ones.

How to ask so it doesn’t feel like an interview

• Pick the right moment. Long drives, walks, a lazy Sunday breakfast or a dinner without phones work best. Not when she’s stressed or about to leave.
• Follow up. Her first answer is just the door. “Why that one?” or “What was that like?” is where the real conversation starts.
• Answer yourself. If you only ask, it feels like a test. Share something too.
• Don’t judge her answers. If you react badly to an honest answer, you’ll never get another one.
• Mix the depth. Start light, go deeper, end with something funny.

Questions to get to know her better

Even if you’ve been together a while, there’s always more to learn. These work well in the first months.

• What was your favorite thing to do as a kid?
• Who was your best friend growing up, and are you still in touch?
• What’s a smell that instantly takes you back to your childhood?
• What were you like in high school?
• What’s the best trip you’ve ever taken?
• Which place would you move to tomorrow if money didn’t matter?
• What’s your perfect lazy Sunday?
• What’s a hobby you’d love to try but never have?
• Which book, film or series changed the way you see something?
• What’s your go-to karaoke song?
• What’s the best piece of advice anyone ever gave you?
• Which family tradition do you want to keep?
• Who do you admire most, and why?
• What’s a skill you’re secretly proud of?
• What’s your favorite memory with your family?
• What did you want to be when you grew up?
• What’s the most spontaneous thing you’ve ever done?
• Are you more of a morning person or a night owl?
• What’s a food you could eat every day for a month?
• What’s something most people get wrong about you?

Deep questions to ask your girlfriend

Save these for quiet moments. They need time and trust.

• When do you feel most like yourself?
• What’s something you’ve never told anyone?
• What are you most afraid of?
• What’s the hardest thing you’ve ever been through?
• What’s a moment that changed who you are?
• What do you wish you had known five years ago?
• What does a good life look like to you?
• What are you proudest of?
• Is there something you’d do differently if you could start over?
• What do you need when you’re having a really bad day?
• Who has hurt you the most, and how did it change you?
• What’s a belief you’ve changed your mind about?
• What makes you feel truly understood?
• What’s something you’re still trying to forgive yourself for?
• When was the last time you cried, and why?
• What part of yourself are you still working on?
• What did your parents’ relationship teach you about love?
• What’s a dream you gave up on, and do you miss it?
• What makes you feel safe?
• If you could ask your future self one question, what would it be?

Romantic questions

• When did you first realize you liked me?
• What was your first impression of me?
• What’s your favorite memory of us so far?
• Which day with me would you live again?
• What’s something small I do that makes you feel loved?
• What’s your idea of a perfect date with me?
• Which song reminds you of us?
• Do you believe in love at first sight?
• What was the moment you knew you could trust me?
• What’s the most romantic thing anyone has ever done for you?
• Where would you like me to take you on our next trip?
• What’s your love language? (If she doesn’t know, do our love language test together.)
• What do you think made us click?
• What’s your favorite photo of us?
• How do you like to be comforted?
• What’s a compliment from me that stuck with you?
• If we wrote a book about us, what would the title be?
• What does “home” feel like to you?
• What’s something you’d like us to do together for the first time?
• What do you love most about our relationship?

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Fun questions

• If you could have any superpower for one day, what would you do with it?
• What’s the weirdest thing you believed as a kid?
• Which fictional character would you date?
• What’s your most useless talent?
• If you were a dog breed, which one would you be?
• What’s the worst gift you’ve ever received?
• Which celebrity would you want as your best friend?
• What would your last meal be?
• If you could only listen to one album for the rest of your life, which one?
• What’s the strangest dream you remember?
• Which of my habits drives you a little crazy?
• If we were in a heist movie, what would my role be?
• What’s your guilty-pleasure TV show?
• What would your autobiography be called?
• If animals could talk, which one would be the rudest?
• What’s the most embarrassing thing that ever happened to you in public?
• What’s a trend you’ll never understand?
• What’s something you’re irrationally scared of?
• If you won the lottery tomorrow, what’s the first thing you’d buy?
• What would you do with an entire day completely alone?

Flirty questions

Light, playful and better with a smile. Keep them for when the mood is right.

• What did you think the first time you saw me?
• What’s your favorite thing about the way I look?
• What outfit of mine do you like best?
• Where’s your favorite place to be kissed?
• What was going through your head on our first date?
• What’s something I do that you secretly find attractive?
• When do you think I look best?
• What would make a perfect night in for you?
• Do you remember our first kiss? What was it like for you?
• What’s the most attractive quality a guy can have?
• What’s the cheesiest pickup line that would actually work on you?
• If we had a whole weekend with nothing planned, what would we do?
• What’s one thing you’d like me to surprise you with?
• What’s your favorite memory of us being silly together?
• What do you think about when you can’t sleep?

Questions about your relationship

These help you notice problems early and show her that you care about how she feels with you.

• What do you think we do really well as a couple?
• Is there something you’d like more of from me?
• Is there something you’d like less of?
• When do you feel closest to me?
• When do you feel far away from me?
• How can I support you better when you’re stressed?
• What’s something I did that hurt you that we never talked about?
• How do you like to make up after an argument?
• What does a good weekend together look like for you?
• How much time alone do you need, and do you get enough?
• How do you feel about my friends?
• Is there something you’ve wanted to tell me but didn’t know how?
• What’s a habit of ours you never want to lose?
• What’s one thing we should try as a couple this year?
• What makes you trust someone?
• How do you show love, and how do you like to receive it?
• What’s a relationship you admire, and why?
• How do you feel about how often we see each other?
• What does commitment mean to you?
• What’s one thing I could do this week to make you happy?

If her answers point to something she’s missing, our guide on how to make your girlfriend feel special has practical ideas.

Questions about the future

Better after a few months together. Ask out of curiosity, not to pin her down.

• Where do you see yourself in five years?
• What’s a big goal you want to reach in the next year?
• Do you want to live in the city or the countryside one day?
• Do you want kids, and if so, how many?
• What would your dream home look like?
• Which country would you love to live in for a year?
• What does your perfect retirement look like?
• What kind of career would make you happy long-term?
• How do you feel about getting married?
• What’s something you want to experience before you turn 40?
• How important is money to you for feeling secure?
• Would you ever start your own business?
• What would you want our home to feel like?
• Is there something you want to learn in the next few years?
• What do you want people to remember about you?

Would you rather questions

Quick, easy and perfect when the conversation needs a lift.

• Would you rather travel the world for a year or have your dream house?
• Would you rather go on a beach holiday or a city trip?
• Would you rather have a big wedding or elope?
• Would you rather always be ten minutes early or twenty minutes late?
• Would you rather never use social media again or never watch another film?
• Would you rather have a cozy night in or a big night out?
• Would you rather be able to read minds or be invisible?
• Would you rather live without music or without coffee?
• Would you rather relive one perfect day or see one day of your future?
• Would you rather cook dinner together or order in and watch a film?

Questions to ask your girlfriend over text

Short enough for a message, interesting enough to get more than “lol”.

• What’s the best thing that happened to you today?
• What are you looking forward to this week?
• What song are you listening to on repeat right now?
• If you could teleport here right now, what would we do?
• What’s something that made you laugh today?
• What’s your plan for the perfect evening tonight?
• What’s on your mind right now?
• Which photo from your gallery best sums up your week?
• What’s one thing you want us to do this weekend?
• What did you dream about last night?

Questions to avoid

Some questions do more harm than good, no matter how curious you are:

• Comparisons with her exes, like “Was he better in bed?”. There’s no good answer.
• Trap questions, like “Would you still love me if I…?” asked seriously. They’re tests, not questions.
• Questions about her body or weight. If she wants to talk about it, she will.
• Jealous questions about her past, asked to judge rather than to understand.

What you say matters as much as what you ask. Have a look at the things not to say to your girlfriend too. And if she wants to turn the tables, send her the questions to ask your boyfriend.