Are you confused about what your girlfriend wants and unsure what to ask her? We have 315 questions to get conversations rolling and build your relationship. 

Questions to Ask Your Girlfriend

Your desire to be intentional in your relationship makes you incredibly attractive to your girlfriend. She needs to be seen and heard by you. 

According to research by Harvard, the amount of talking done by men and women is situational, and women talk more when seeking collaboration. As you ask questions, approach it as a way to develop attunement and connection together. If she senses you’re seeking relational collaboration, she’ll be more prone to open up and communicate how she feels. 

These questions will help you attune to your girlfriend by learning about her heart, values, and needs. 

So ask the questions, and please make sure to listen. 

We created a FREE conversation starter app just for you! Our goal is to help all fellow recovering awkward people. The team put together 1,000 of the best conversation starters on a simple app you can reference in the car or bathroom on your way in:

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  1. What is your most treasured memory?

Get your girlfriend talking about positive things—the memories that give her all the good feelings and make her smile. Even though you weren’t there, when she shares those memories with you, it connects you to a piece of her past. 

As you grow in your relationship, change this question to, “What’s your favorite memory about us?” or “Do you remember when we…?”. Memories help us make sense of who we are and can even remind us of what we care about. Make sure to take time to make space in your relationship for both memories that you share and memories that have shaped you separately. 

  1. How have your parents impacted your view of love and relationships?

This is a big one. 

Did she grow up in a secure family environment? Did her parents show her healthy love or cause her to doubt or even fear love relationships? Don’t probe too deeply on this one if she seems closed to sharing. The fact she doesn’t want to talk about it says a lot. 

Revisit it later once you’re closer and have more trust between you. 

Pro Tip: If she is cynical about love, ask whether she’s ready for a serious relationship right now. If this is an area she is working to improve, you’ll need to develop open communication early on. Find out what she needs to feel safe and secure in the relationship. 

  1. What are some of the cultural pressures that people put on you as a woman? 

Every woman faces layers of pressure on her body, her career, and the checkpoints of success. Society and family often place expectations of how to be sexy, beautiful, and successful without being too sexy, too beautiful, and too successful. 

Just like the pressures and expectations you face, there’s a fine line that people expect a woman to walk. How is that impacting her? How can you support her?

Understanding this will help you be more sensitive to her emotions, and you’ll know why she makes certain choices. 

If she’s from a different culture, this question allows her to explain how her culture sees a woman’s role differently than your culture does. 

  1. What question have you wanted to ask me? 

Sometimes, a woman needs you to make it easy to ask questions she might not naturally yell out in the middle of a conversation. 

Maybe she wants to know if you’re married with 12 kids, but asking feels awkward, and she doesn’t want you to be offended. 

But she really, really needs to know. 

Or maybe she wants to know if this is serious for you or if you like her. 

By asking her this question, you indicate that it’s ok to ask whatever is on her mind. 

Pro Tip: Don’t get offended by her question, whatever it may be. Instead, show you have nothing to hide and that you are confident and secure without needing to be defensive. 

  1. What are your 5 travel essentials? 

What does she value so much she can’t live without? Ask follow-up questions to spark further conversation and dig deeper into her values. 

Follow-up questions based on possible travel items:   

  • A book: What kind of books do you like to read when traveling?
  • Sacred writings/religious books: What is your spiritual practice? Why is it important to you? 
  • Journal: Do you record your thoughts or just the things that happen each day? How long have you been keeping a diary? 
  • Clothing steamer: Is image important to you? Why? 
  • Extra shoes: What is your favorite pair of shoes? Do you have any shoe disaster stories (have you broken a heel or had to run in heels?)? 
  • Minimalist wardrobe: Do you value efficiency most? What if I’m an over-packer? 
  • Skincare products: What’s your favorite skincare line (remember this as a possible gift later)? What skincare products do you think men should use? 
  • Slippers: Do you wear shoes in your house? Fuzzy slippers or plain and functional? 
  • Snacks: Do you have dietary restrictions that make travel harder? What’s your favorite travel snack? 
  • Power Pack: Do you work while you’re traveling? Did your phone ever go dead when you were traveling? Did it lead to a travel mishap? 
  • Headphones: What do you listen to? Music? Podcasts? Language lessons?
  1. What was the best gift you’ve given someone else? 

If she’s thoughtful and unlikely to brag on herself, this question shows you a part of her she might keep quiet. You’ll also learn about how she thinks and maybe even how sneaky she can be when planning a surprise. 

Follow-up questions: 

  • How did they respond? 
  • How did you know they would love it? 
  1. What was your favorite book in high school? What’s your favorite book now?

This is a fun question that can lead to conversations on what she was like in high school and how she’s changed over the years. Hopefully, she has! You want a girlfriend who grows with her experiences and hasn’t stayed in a strange time warp of never changing.

Follow-up questions:

  • What did/do you love about the book? 
  • Who was your favorite person?
  • Do you think it should have had a different ending?
  • What do you identify with in the book? 
  • Have you read other books by that author? What did you think? 

Pro Tips: 

  • If you haven’t read those books, offer to do a book swap. You’ll read her favorite book if she reads yours. 
  • If you hate books, ask if there is a movie version of the book and watch it together. 
  • If neither of you is a reader, talk about your favorite movies or TV shows. 
  1. What are your physical boundaries?

This is a great question to ask early in the relationship, so you’re both on the same page. Find out what she’s comfortable with and what her cultural or religious beliefs are around physical intimacy. 

Nonverbal cues can be informative, but remember, they aren’t the primary indication of consent! And we aren’t just talking sex here—different women will have other desires and expectations of what is appropriate and when. 

Having an open conversation demonstrates respect for her and gives you a chance to share your cultural or religious beliefs if they are different than hers. 

  1. What was your favorite breakfast cereal as a kid? 

Was she the kind that drank the sugary milk after the cereal soaked in the bowl for a disgusting amount of time? Or did her single mom only get Kix as a special treat because they didn’t have money to buy it regularly? 

You can learn much about her background from this fun and innocuous question. If all you discover is a shared obsession with Cocoa Puffs, this question is a warm and fuzzy dose of nostalgia.

  1. What do you believe about life after death? 

Do you have compatible spiritual views? Find out the answer to this question early on, and explore how important it is to be consistent in this area. 

For some, this is a dealbreaker. 

Down the road, you may face questions about what spiritual belief to raise the kids with, and there may be tensions between your two families. Even if you aren’t looking at marriage any time soon, these are questions to explore early and determine where you’re willing to flex and what isn’t negotiable. 

  1. What do you wish a guy would ask you but never has? 

If you want her to feel attracted to you, give her control of the conversation. Ask her a question, “I don’t expect to do all the talking in this relationship. I want to hear what you say, and I’m open to discussing what is important to you.” 

You’re also positioning yourself to be different from other guys who may have let her down, even in subtle ways. 

Pro Tip: While she’s talking, lean forward, quickly nod three times, and keep your ears open. Maintain good eye contact so she knows you care about the answer to this question.

Want more communication tips? Check out 10 Effective Ways You Can Improve Your Communication Skills

  1. What do you wish people knew about you?

Sometimes, women get placed in a box by choices from their past or family expectations. 

Give her a chance to share who she is and that you want to see the real her. 

She may feel overlooked and underestimated by others but knows she has leadership skills. 

Maybe she was one in high school, but today she’s completely different. If she still lives in the same community, other people may be holding her back; they still view her as the teenager they used to know. 

More than anyone in her life, she needs you to see her for who she is and who she could become. This can be a vulnerable question, so when she shares, ensure you build her up and encourage her to live up to her potential. 

  1. What gets you out of bed every morning? 

Learn about her passions and what gives her purpose every day. You may also find out about responsibilities you didn’t know she had. Maybe she has a child she didn’t tell you about yet, or she lives with her sister and helps take care of her nephew. 

Whether it’s family ties or an entrepreneurial endeavor, you’ll get a picture of her life and where you might fit in it. 

  1. What signs can I look for to know when you aren’t ok? 

You know you’ve hit the danger zone when your girlfriend says, “I’m fine,” or, “It doesn’t matter.” Or even worse, the wall of silence. 

What if you could improve communication and pick up on the signals before she’s “fine”? 

She might start compulsively snacking or pacing the floor. Maybe she starts baking or becomes inexplicably critical of everything you do. Learn her coping mechanisms, so you know when to give her support and when to give her a little space.  

This question will also show how self-aware she is and whether this is something you’ll need to work on as a couple. 

Follow-up questions: 

  • When you’re upset, do you need space or support?
  • Should I ask you questions or just sit with you?
  • Do you want food or gifts to cheer you up, or do you need me just to hold you?
  • Can I ask what you need when upset, or does that make it worse?

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Control and leverage the tiny signals you’re sending—from your stance and facial expressions to your word choice and vocal tone—to improve your personal and professional relationships.

  1. What do you like most about yourself?

How does she perceive herself? Does she underestimate her positive qualities or overestimate them? It’s good to know how she views herself, and you can even build her up in the areas she feels strongest. 

Pro Tip: After she answers, tell her what you like most about her (hint: now is not the time to compliment her butt or her lips, stick to character qualities).

  1. Can we talk about our health histories? 

It’s never comfortable to ask someone if they have mental or physical concerns, but when you’re in a relationship, it’s essential to know what your SO is struggling with. 

For example, if she has an autoimmune disease, she probably won’t have the strength to keep pace with you and could find endless outings exhausting and painful. 

If either of you is struggling with mental illness or physical concerns that require medication, it’s helpful to know what those medications are. You may have to take some medicines simultaneously every day, while others cause restrictions on things like alcohol consumption.

Don’t be afraid to ask, and make sure you answer the questions too. 

If either of you has a health concern the other person doesn’t understand, share your limitations and how the other person can be more supportive. Make sure to find out what their physical and emotional triggers are and learn their emergency plan (e.g., emergency meds, epi-pen, on-call mental health professional, trusted family member, etc.).

  1. If you’re angry, what do you do? 

Is she passive-aggressive? Does she hold a grudge just waiting to get even? If this is an area she’s working to grow in, progress slowly and pay attention to any toxic patterns that emerge. Help her express her emotions so you can work through them together.

If she doesn’t see this as a problem or even thinks it’s funny, you’re looking at a relationship that could turn toxic very quickly. 

  1. What are your political views and ideals?

If you’re starting to get serious, do a values check. Do you have similar political views, and if not, are you comfortable with that?

It’s possible to love someone with different political views than yourself but explore early on whether you are comfortable with that tension. Some ideals may be deal-breakers for one or both of you, and that’s important to know before getting too far in the relationship. 

If it’s not a dealbreaker, talk about how you can hold differing views and still be respectful of the other person. 

  1. What do other people do that frustrates you?

Learn how she handles stress and what her pet peeves are. If you know her frustrations, you can avoid annoying her. You can also keep an eye out for when she’s getting frustrated and help by distracting her attention or saying something funny. 

  1. What are your favorite things to do?

It sounds like a simple question, but it gives you important information. Ask this early (even on the first date) to find out what you have in common. 

It might sound odd, but follow up by asking if she does her favorite things! 

She may be in a season of her life where busyness and accomplishing her goals have pushed out the things she loves to do. This is an excellent opportunity to surprise her by incorporating her favorite things into your following dates. 

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Deep Questions to Ask Your Girlfriend 

Not sure how to get to know your girlfriend? Ask these deep questions to open up conversations. Get her telling stories, and the conversation will flow. 

Woah that's deep bro meme
  1. What makes you happy? 
  2. What are your short-term and long-term goals? 
  3. What kind of mom do you want to be? (If she wants to be a mom in the first place)
  4. Who inspires you? Why?
  5. Have you experienced gender disparities/discrimination in your workplace? How do you handle that? 
  6. What is an obstacle you’ve had to overcome?
  7. What’s the highest level of education you’d like to get? (If she doesn’t already have her Ph.D.)
  8. What’s something you’re passionate about that you never get a chance to discuss? 
  9. How would you define success? Do you feel successful? 
  10. What does friendship mean to you? 
  11. What friends have shaped your life the most? 
  12. If you knew you were going to die and could only send one text, who would you send it to, and what would you say? 
  13. What’s something you’ve always wanted to do, but others made you feel like you couldn’t accomplish? 
  14. What do you think [insert country here] should change about its foreign policy? 
  15. What do you think your industry could do better (insert whatever industry your girlfriend works in)?
  16. What are you most proud of? 
  17. What was the most important moment in your life?
  18. Is it ever OK to lie? If so, why or in what situation? 
  19. Who do you feel listens to you the most? 
  20. How can people grow together instead of apart as they grow older? 
  21. If there was a clone of you who had an opposite personality, what would they be like? 
  22. What’s your favorite book? Convince me why I should read it.
  23. What impact do you think artificial intelligence (AI) is having on society? Do you think we should have more or less AI? 
  24. What was the biggest decision you ever made? What happened? 
  25. What’s something you didn’t realize about yourself until someone else told you?
  26. Could you ever (or have you ever) been in a long-distance relationship? 
  27. What’s your favorite memory with your dad? How did he make you feel about yourself?
  28. What do you do if you face something you fear? How can I help empower you to face your fears? 

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Cute Questions to Ask Your Girlfriend 

All your questions don’t have to be deep ones. Ask cute questions to build positive emotions. 

  1. What is your favorite love song? 
  2. I need to buy a present for my mom; will you help me? 
  3. Are you a good dancer? 
  4. Do you think Lucy secretly loved Charlie Brown? What other cartoon enemies should have ended up as a couple? 
  5. What movie can you quote the most lines from? Quote your favorite part of the movie to me! 
  6. What was your favorite toy as a kid? 
  7. What song makes you think of me? 
  8. What does it feel like to you when you fall in love?
  9. I love when you wear __. Will you wear that to our date tonight? 
  10. I still get butterflies when you walk into the room. Do you feel that way too? 
  11. What’s something I could do that would be embarrassing to me but would make you feel loved? 
  12. What’s your favorite memory of us? 
  13. Let’s get dance lessons together. What kind of dancing do you want to learn? 

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Fun Questions to Ask Your Girlfriend 

These fun questions will teach you more about her thoughts while keeping them light. If her answers get serious, just go with it!  

  1. Who is your favorite artist?
  2. What’s your favorite place? 
  3. Your house is on fire, and you can save 1 of 3 things. Your favorite book, your good tweezers, or your favorite mug. Which would you choose and why? 
  4. Have you ever been out of the country? If yes, tell me about your favorite trip. If not, where would you like to go?
  5. What is your favorite State? What do you love about it? 
  6. Which of the 7 wonders of the world have you always wanted to see? Have you seen any of them already? 
  7. What’s your middle name? Who gave you your middle name, and what’s the story behind it? 
  8. What’s your favorite music station?
  9. What’s your favorite action movie? What did you love about it? 
  10. What’s your favorite dessert? 
  11. If you were an animal, what animal would you be? 
  12. What does your ideal weekend look like? 
  13. Have you ever taken a fake sick day? What did you do? 
  14. Tell me about your friends. What are they like? Do you have a BFF? 
  15. What do you like to do with your friends? 
  16. Do you like your friends? Do you think they’ll like me? 
  17. What’s your favorite thing to relax in the evenings? 
  18. Do you cook more or eat out more? If you like to cook, what’s your favorite thing to cook? 
  19. Do you like movies or books better?
  20. What movie is way better than the book? What movie ruined the book for you?
  21. Have you ever wanted to write a book? What would you write? 
  22. Tell me about any famous or interesting people in your family history.
  23. Tell me about your best vacation. 
  24. Tell me about your childhood pet. If you’ve never had one, would you like one? What kind? 
  25. What isn’t an Olympic sport but should be? 
  26. What’s your favorite but lame and outdated slang word or expression? 
  27. How old do you feel? 
  28. What food have you always wanted to try? What food do people think is gross that you love? 
  29. Have you ever changed someone’s opinion on something? What was it? 
  30. If you could have any job, regardless of whether you have the experience or not, what would it be? 
  31. Are you a cat or dog person?

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Serious Questions to Ask Your Girlfriend 

As you get to know each other, it’s time to ask more serious questions. These questions will help you explore past experiences and understand some of the things she may be struggling with. 

  1. How did your last relationship end? 
  2. Do you want children?
  3. Do you already have children? 
  4. What is your relationship like with your father? 
  5. Do you see marriage in your future? 
  6. What are your views on money? Do you have financial priorities or goals?
  7. Where are you in the birth order? Is there sibling rivalry in your family? How close are you to your siblings? 
  8. Have I ever made you feel less for being a woman? How? 
  9. What do people make jokes about that you find offensive? 
  10. Who in your family tends to dismiss or belittle you? What do you do when that happens? 
  11. What makes you feel fulfilled and gives you purpose? 
  12. If you are hurt or crying, how can I comfort you, or what do you need? 
When someone is crying and
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  1. Do you think you’ve made your parents proud?
  2. If you could start a nonprofit, what would it be for? 
  3. Have you ever been part of a protest? What made it important to you? What did it feel like attending the rally? 
  4. What do you judge yourself most harshly about? 
  5. Does aging scare you? How do you think people can age gracefully? 
  6. Tell me about your favorite and least favorite teachers.
  7. Do you think we’re a positive influence on each other? Do I bring out the good in you?
  8. What do you like most about our relationship? 
  9. What do you wish was different about our relationship? 
  10. What negative things made you stronger?
  11. Is there anything you feel you’d be giving up to be in a relationship with me? 
  12. Is there anything you need help with right now? 
  13. How have you been feeling about ___ negative situation? 
  14. Do you have any big meetings or things coming up that you’re feeling nervous about? How can I help? What do you need to feel supported?
  15. You’ve been through a lot lately. What can I do to pamper you this weekend? Spa day? Picnic? Takeout and movies? Day trip to your favorite art museum? 
  16. I’m so proud of what you’ve accomplished this year. We should celebrate (insert big or small accomplishments). What would you like to do to celebrate? 
  17. What do you love about your job? What do you wish you could change about it? 

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Romantic Questions to Ask Your Girlfriend 

Your girlfriend needs you to ask questions about emotional and relational intimacy. Whether it’s talking about sexual expectations or what makes her feel heard, you can make it easier by starting the conversation. 

Also, don’t assume that every woman loves red roses or that just because she’s giving you all the cues that she’s ready to have sex. Talk openly about what you both are expecting and needing and what you both feel makes for a healthy relationship. 

  1. What makes you feel sexy?
  2. What do you believe love is?
  3. Do you believe love can last forever? 
  4. Do you like big displays of affection? 
  5. How do you feel about PDA? 
  6. What is your favorite flower? 
  7. What’s your favorite date night movie? 
  8. What’s something you love to do but rarely get a chance to do it?
  9. What are your personal, cultural, or religious beliefs about physical intimacy?
  10. How can I know if you want more or less physical intimacy? 
  11. I want to make sure you are always comfortable and in control of your own body. Will you tell me if I’m moving too quickly? 
  12. How can I show you love? 
  13. What’s your love language? 
  14. Are roses and teddy bears romantic to you? Note: If she says no, start listening for her likes or things she expresses interest in. Alternative ideas: Find the first edition of her favorite author, deliver pastries to her work, get her favorite takeout for two and show up at her work for a surprise lunch date, fuzzy slippers, a subscription box from one of her interests (art, crochet, makeup, etc.). 
  15. Do you think public proposals are romantic? What would be your ideal proposal? 
  16. What would be your ideal birthday celebration?
  17. What would make you feel loved and cared for by me? 
  18. Do you keep in touch with your exes? 
  19. Do you feel heard by me? 
  20. Do we spend enough time together? 
  21. Do you wish I would be more affectionate? How can I be more loving? 
  22. How can I better support your career goals? 
  23. What’s your ideal Valentine’s Day?
  24. What’s your idea of a romantic date? 

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Intimate Questions to Ask Your Girlfriend

You’ve been together long enough to develop trust, and both are interested in long-term commitment. 

It’s time to take things deeper and start asking questions to understand what your girlfriend has gone through and how that might impact your relationship. When you know the hurts or wounds she experienced, you can avoid hurting her (even unintentionally!) in those same ways. 

  1. What is your biggest fear for our relationship? 
  2. Have you ever been cheated on? How can I help you feel secure in our relationship?
  3. What do I do that triggers you?
  4. What do I do that reminds you of past bad relationships?
  5. Do I remind you of your dad? Is that good or bad? How can we work through that together?
  6. What makes you feel safe? 
  7. Have you been in therapy? 
  8. What have you learned about relationships from therapy?
  9. What are your coping mechanisms?
  10. Are you able to have children? If not, would you want to adopt or foster?
  11. What does our future look like to you? 
  12. What things make you feel afraid?
  13. What was your childhood like?
  14. Do you have bad memories from your past? Have you started working through those? If you feel safe talking about it, I will listen without judgment. 
  15. How did people treat you in school?
  16. What role does your family expect you to play? Do you feel hurt or limited by that? 
  17. Who are you closest to? Your mom or dad? Did you feel loved and accepted by your parents? 
  18. If you could make a phone call to yourself at any time, when would it be, and what would you say? 
  19. What’s something I used to do at the start of our relationship that you miss, now that we’ve been together for a while? 

Pro Tip: Don’t ask direct questions about possible abuse, such as, “Have you experienced domestic violence?”. 

She may not be ready to tell you about the things she has experienced, and a direct question takes away her ability to choose. Plus, she may have had past boyfriends who shamed her for the abuse she experienced. If you suspect she has gone through some negative experiences, wait for her to initiate the conversation.  

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Random Questions to Ask Your Girlfriend 

These random questions range from silly to serious, all to learn more about each other. 

  1. What movie made you cry the hardest? 
  2. Which is better, K-dramas or crime dramas? Tell me about your favorite one. 
  3. What do you do when you feel bored?
  4. Night owl or early bird? If you’re a night owl, what’s your favorite thing to do at night? If you’re an early bird, how do you like to start your day? 
  5. What historical person do you wish you could meet? 
  6. Who do you think was (or is) the best political leader of all time? 
  7. What’s the most underrated movie of all time? 
  8. What should more people know about? 
  9. If you could write your eulogy or the inscription on your tombstone, what would it say? 
  10. What villain do you secretly admire? Why? 
  11. Heels or sneakers? 
  12. How do you like your eggs? 
  13. What unhealthy food will you never give up? 
  14. Is it too early to post pictures of us together on Facebook? 
  15. At what point in the relationship should a couple change their Facebook status to dating? 
  16. How private are you? Do you like posting everything to social media? 
  17. Are you friends on social media with your exes?
  18. What was the best part of your week? 
  19. Do you have any big projects you are working on at work?
  20. What’s your biggest stressor right now? 
  21. What song do you listen to on repeat? 
  22. Have you ever cried in public? What happened? 
  23. What’s your favorite holiday? Why?
  24. What’s your favorite holiday memory? 
  25. How do you celebrate Christmas as a family?
  26. What obscure holiday do you love?
  27. What’s your favorite season?
  28. Is pumpkin spice an essential part of your life? Why or why not? 
  29. Do you like to go for hikes? Do you prefer indoor or outdoor activities? 
  30. Do you prefer receiving cut flowers or plants? 
  31. What’s your favorite board game? Are you ruthless, or do you play for fun? 

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Flirty Questions to Ask Your Girlfriend 

Wish she’d look at you like the leading man in her favorite Kdrama? Skip the dramatic (and painful!) wrist grab and ask her these flirty questions instead. 

  1. What’s your favorite type of kiss? 
  2. Do you know why you always make me smile? 
  3. Do you think about me a lot? 
  4. What makes me attractive to you? 
  5. What did you like about me when you first met me?
  6. What do you like most about me now? 
  7. I’m cooking you dinner tonight. What do you want me to make you? 
  8. If she prefers staying in, send her this text: Put on your PJs and pick your favorite movie. I’m coming over with takeout. What’s your favorite? 
  9. If she prefers to go out, send her this text: What do you want me to wear tonight? I’m taking you dancing. 
  10. Do you like it when I wear cologne? Do you have a favorite scent? 
  11. What do you love seeing me wear? Is there something you wish I would wear sometimes? 
  12. Who is my celebrity doppelganger? 
  13. How would you describe me to your friends? 
  14. What do I do that you think is cute?

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Funny Questions to Ask Your Girlfriend 

She likes it when you can make her laugh. These questions will allow you to laugh together, even if you aren’t funny. 

  1. What reality TV show would you cancel? What reality TV show needs to exist that doesn’t?
  2. What secret fear did you have as a kid that you now realize was ridiculous?
  3. What is on your New Year’s resolution list every year? 
  4. If you could be a llama or a panda bear which would you be and why? 
  5. What do you think your pet thinks about you?
  6. If you could pick a food to smell like, what would it be?
  7. What’s the funniest nickname you had? 
  8. If your friends and family heard you were arrested, what crime would they think you had committed? 
  9. Tell me about your worst haircut. Are there pictures? 
  10. Have you ever used a pickup line on someone? What happened? 
  11. Do you like your laugh? How would you describe your laugh based on the sound an animal makes? Choose from: Donkey, seal, pig, crow, pigeon, or a dog with asthma.
  12. Tell me your best joke.
  13. What vegetable would you be? What vegetable would I be? 
  14. What words do you pronounce strangely or have trouble saying?
  15. Are you competitive? If so, tell me about a time you were inappropriately competitive but still reveled in your victory. 

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Interesting Questions to Ask Your Girlfriend 

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  1. What is the most surprising thing you’ve ever done?
  2. What was your worst job?
  3. Who is the craziest person in your family? 
  4. Do you prefer to give or receive? Why?
  5. Who is your favorite person? 
  6. What skill are people usually surprised you have? 
  7. Do you speak another language? Why did you choose that language to learn? 
  8. What’s the most surprising or exciting conversation you’ve had with a stranger? 
  9. What’s the best relationship advice you’ve been given? 
  10. Would you ever give up your dreams for love or give up love for your goals? 
  11. What’s your favorite comfort food? How do you make it? 
  12. What did your mom (or dad) always do when you were sick?
  13. Tell me about a typical day at work? Is it stressful? How do you make decisions? 
  14. What are your coworkers like? Are you friends with any of them?
  15. What’s something you wish you had started planning for when you were younger? 
  16. What is something you learned early that your friends didn’t? 

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Questions to Ask Your Girlfriend about Yourself 

Wondering what she thinks about you or what you can do to be a better boyfriend? Ask her! 

  1. What do I do that makes you feel hurt or unloved?
  2. What song reminds you of us? 
  3. How could I be a better boyfriend? 
  4. What do I do that makes you laugh?
  5. How can I be a more supportive boyfriend? 
  6. What do I do that drives you crazy?
  7. Do you think I’m living up to my potential?
  8. In what area of my life do I let others cut me down? 
  9. What do I do that makes you feel rejected? 
  10. How do I make you feel when we hang out with my friends? 
  11. What positive characteristics would you use to describe me?

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Unique Questions to Ask Your Girlfriend 

Ask questions that reveal something unique or surprising about your girlfriend.

  1. What do most women love that you just don’t care about? 
  2. What role do you play in your friend group? 
  3. What is the most essential personality trait in a man? 
  4. What’s a skill you want to learn? Can we learn together? 
  5. What song do you wish was written about you?
  6. Have you ever written a song or poem about someone? 
  7. Do you think we would make good parents together? 
  8. What is one city or country everyone wants to visit that you don’t? 
  9. What do you think strangers think about you just by looking at you? 
  10. What is one social norm you would remove if you could?
  11. How have I changed since we started dating? 
  12. How have you changed since we started dating? 
  13. What character quality have you lost as an adult that you wish you still had? 
  14. What is your definition of femininity? 
  15. What is your definition of masculinity? 
  16. What is something your parents don’t know about you? 
  17. Have you ever ridden a camel, a donkey, or an elephant? Tell me the story! If not, which of those three would you like to ride? 
  18. Have you ever gone scuba diving? If not, would you want to and where? 

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Weird Questions to Ask Your Girlfriend 

A little weird, and a little random, these questions can be good icebreakers or used when the conversation is lagging. 

  1. What was the weirdest conversation you overheard? 
  2. What’s something your family thinks is normal but weird?
  3. Should Pluto still be considered a planet? 
  4. What was the weirdest dream you’ve ever had? 
  5. If you could name yourself in the will of one of your friends, who would it be, and what would you inherit? 
  6. What social media post do you regret?
  7. What do you think about people who wake up from a coma able to speak a language they never learned? 
  8. What do you think is the weirdest animal? Why?
  9. Would you rather eat like an anteater or have a long neck like a giraffe? 
  10. How vital are pillows? 
  11. What was the weirdest situation where you had to be polite when you didn’t want to be?
  12. What is the weirdest thing you’ve eaten?
  13. Do you talk to yourself? 
  14. What was the most expensive thing you regretted buying? 
  15. What’s something you’d never tell your boss?
  16. What colors have you dyed your hair? 
  17. Do you make your bed every morning? 
  18. What song would you want at your funeral? 
  19. Is it stealing if you keep someone’s pen? 
  20. What color pen do you prefer writing with?
  21. If you could be taller or shorter, which would you choose?
  22. Do you keep a physical day planner or use your phone? 
  23. If you were a dog, what breed would you be? 
  24. What’s your opinion on fanny packs? 
  25. Should pizzas be square? Why or why not? 

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Cultural Questions to Ask Your Girlfriend

If you’re dating someone from a different culture, it’s easy to be confused or have miscommunication. Ask your girlfriend questions about her culture to know what to expect. This will help to minimize conflict and lay a foundation to navigate your differences. 

  1. What do other people do that is offensive to your culture?
  2. Will you tell me if I do something offensive?
  3. What expectations will your family have for me?
  4. What are some stereotypes about your culture that you think I have towards you?
  5. What are some stereotypes that you have about my culture? 
  6. How can I show respect to your family?
  7. Should I refer to your older family members by name, or should I call them something different like Auntie or Uncle? 
  8. How should I interact with members of the opposite sex in your family?
  9. What will your parents expect me to do when I meet them? 
  10. How should I interact with you in front of your parents? Is it ok to hold your hand or put my arm around you in front of them? 
  11. What obstacles or prejudices have you had to overcome?
  12. Are there any foods or drinks you can’t have in your culture? 
  13. What are the expectations for women in your culture? 
  14. Does your culture have any negative views of dating? How can we navigate that so your community doesn’t gossip about you?
  15. What do you love most about your culture?
  16. Can you cook me your favorite meal? 
  17. What language(s) do you use to communicate with your family? 
  18. What should I do during the meal with your family?
  19. Is there anything I should bring to give your parents when I meet them?
  20. Are there any religious traditions that could impact when or how we can date? 
  21. Can you teach me how to say “thank you” in the language of your family? 

Does your girlfriend need a list of questions too? 325 Questions to Ask Your Boyfriend

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