43 Questions to Ask Your Girlfriend

Relationship Rules
18 Jun 2023
18 min read
43 Great Questions to Ask Your Girlfriend

The best relationship advice anyone can give is to simply ask your girlfriend questions. Get her talking about her favorite things, what she likes and dislikes, and more. By looking for questions to ask your girlfriend, you’ll be able to have a better understanding of her and a more stable relationship.

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Fun Questions to Ask Your Girlfriend

To ease your way into that unknown territory of who is that woman in front of you, use these most random questions; they are the best to ask. Keep them fun and simple, yet completely open to answers from all areas. Here are some of our favorite fun questions you can ask her.

1. What are 5 things you always have with you?

This is one of the most fun questions you can ask because as much as you expect something, there is always a way to surprise you. By asking this question, you provide them an opportunity to list any item, as long as it is small enough to fit into a purse or in their pocket. Don’t forget to list your own essentials to make your chat more fun!

2. What is your favorite movie?

A person’s favorite movie can tell you a lot about them. For example, a person who enjoys something from Studio Ghibli may find romance in the little things that they come across in life.

You may also find that your opinions of movies are on the same page. If she does not have a favorite movie that she can think of, change the question and ask her what the most underrated movie is in her opinion.

3. Did you have a favorite breakfast cereal mascot as a kid? If you did, who was it?

One of our favorite random questions you can ask. It makes the person think of their childhood self and what kind of media they were exposed to. If you have a long-distance relationship, you may learn of a character you had never even heard of.

Related reading: Does Distance Really Make the Heart Grow Fonder?

4. Do you prefer indoor or outdoor activities?

This is a pretty important compatibility question. If one of you loves the outdoors and the other prefers the indoors, that could cause problems. Better be sure you have other interests in common!

5. Do you have a favorite reality TV show?

Does she love the drama of Real Housewives, the excitement of competition style shows, or does reality TV turn her off entirely? Better find out if you have something you can binge watch together!

6. What bad habit annoys you most?

Sometimes, the smallest things can be big frustrations. This interesting question can kick off a conversation about habits that make her teeth itch.

Related reading: 21 Things Your Partner Should Never Say to You (and Vice Versa)

7. What’s your favorite thing in your home that costs under $5?

This one is a bit lightweight, but it’s a fun way to get her engaged in conversation. Sometimes, we buy a cheap little item on a whim that becomes a prized possession. Alternatively, we might land an amazing deal online or at a thrift store. So, find out the story behind her cheapest treasure.

8. What’s your favorite thing in your home that costs more than $100?

Now, let’s head to the other side of the spectrum. Does she have a piece of artwork, electronics, or other item that brings her great pleasure? It’s fun to talk about the luxuries we all enjoy.

Dirty questions to ask your girlfriend

Dirty Questions to Ask Your Girlfriend

Even a healthy relationship needs to get away from those deep and meaningful questions in order to get a bit messy. You can make asking your girlfriend dirty questions a post-date night game that makes spending time with her even more fun. Also, these sexy, cute questions can help make you a better lover for her.

9. What is your favorite toy, or what would you see becoming your favorite toy?

This is a bit of raunchy question that gets right down things. Yes, it’s a bit forward, but the more you know about her tastes the better.

10. What is your least favorite sexual position?

What if your favorite position is one she hates? Can you get past it? You never know unless you ask.

Related reading: How to Be a Better Lover – Inside and Out

11. What is the best compliment I can use to make you feel sexy?

Sometimes, conversation is the best kind of foreplay. If you can learn how to talk her into the mood while also making her feel great about herself, your love life will be amazing.

12. Do you enjoy dirty talk or does it make things weird for you?

Some women aren’t very comfortable with pillow talk. It makes them feel awkward and takes them out of the moment. It’s good to know her preferences here so you can make sure sex is fun for both of you.

Related reading: Want Some Spice? Add a Sexual Surprise to Your Sex Life

Romantic Questions to Ask Your Girlfriend

When you are with someone in a romantic sense, it’s good to get to know them and their feelings on that level. Here are some of our favorite romantic questions that you can ask.

13. What would the best date night look like during your favorite season?

Most women have a favorite season. They love the aesthetics, the seasonal food, the holidays, and the activities. Wouldn’t it be great to plan an amazing date night around that?

Ask her what she loves. For example, you might plan a fun trip to an apple orchard followed by a picnic with some hard apple cider if her season is autumn.

14. Without telling me what it is, how would you describe your favorite flower?

This is a fun conversation starter that lets you ask a question that requires more than a one or two-word answer. Of course, you’ll want to keep her favorite in mind for your next romantic gesture.

15. What’s your most romantic memory?

No, you shouldn’t try to recreate something her old lover did to make her happy. Instead, use this question to get a general idea of what she truly appreciates. Then, keep that in mind as you plan your own romantic experience with her.

Cute questions to ask your girlfriend

Cute Questions to Ask Your Girlfriend

When you want to get your girlfriend talking, one of the best ways to get them to do so is by asking them a series of funny questions.

16. What is the favorite gift you have ever given someone?

People show romantic and platonic affection in different ways. By asking her this, you make her think more critically of herself and your place in her life.

Her favorite gift may also take you by surprise. You may expect that it’s something grand and expensive but in reality, it’s something pure and simple that only made somebody smile.

Related reading: Appreciating a Platonic Soulmate

17. What are 3 things you want in your dream wedding?

This is a great question, but do not ask this on the first date. Also, if she asks you this question on the first date, that might be a red flag. But, if you have been dating for awhile, go for it!

18. Have you ever thrown a surprise party for someone?

Have you ever thought about what it takes to throw a surprise party? Someone who does that has to be extraordinarily well-organized and able to keep a secret.

Who knows, you might see that as a positive in a girlfriend? On the other hand, maybe you just want to be warned that she might try to throw a surprise celebration for you one day too!

19. How do you celebrate your favorite holiday?

Are you and she holiday compatible? Some people prefer major blowouts, while others like to keep their holiday observances low-key. This question will help start a conversation about holidays you love and how you celebrate them.

Related reading: 21 Questions for a New Relationship

Interesting Questions to Ask Your Girlfriend

As we have learned over time, women are not nearly as of a mystery as one would believe. However, there are some things that people don’t fully grasp when it comes to them. When you don’t understand something, the best way to gain understanding of it is to ask questions. And this list of interesting questions to ask your girlfriend is the perfect roadmap to comprehend who is that woman is front of you!

20. What was your favorite playground game as a child?

Every elementary school playground is home to favorite playground or recess games. There are universal favorites, and some regional games as well. Some games are well-loved. Others, like dodgeball, are a bit controversial.

So, did she spend her recess time quietly swinging. playing tether ball, or playing winner-takes-all games of capture the flag? You have to ask to find out!

21. What are 3 things on your bucket list that you don’t think anybody else has on theirs?

Even if they don’t have an official bucket list, most people have thought about what they want to accomplish or experience. Some list items are pretty universal, such as traveling the world. Others are things that are quite unique. These are often the most interesting. So, find out what bucket list activities she has that most people have never considered.

Deep and serious questions to ask

Deep Questions to Ask Your Girlfriend

Okay, these aren’t all that serious. However, they are the kind of questions that definitely make people think. In some ways, they are a bit philosophical.

22. What is your favorite memory?

You can learn a lot about a person by what kind of memories they hold close to their heart. If their favorite memory has to do with a family trip or vacation, they may feel strong bonds with their family and might even want to start one. If their favorite memory concerns an animal or a pet, they are likely very compassionate and caring. By asking her to talk about her favorite things, you get a closer look at her as an individual.

23. Are you a cat person or a dog person?

Although you can like both cats and dogs, people do tend to have a preference that relates to their own personality.

People who enjoy dogs tend to be social, active, and easy to get along with. They will happily come to you and even be your best friend before you start to date. A person who prefers cats may be a bit more shy and reserved. They may be somewhat of a recluse and may also not accept affection as easily. They may also be a bit more of a night owl as well.

This is such a simple question to ask but it does reveal a lot about who she is.

24. Do you live the way your parents expect?

Did her parents have dreams of raising a doctor, but got a tattoo artist instead? Find out if she is someone who lives up to expectations or a bit of a rebel.

Related reading: How To Maintain Your Individuality While In a Relationship

25. What would your dream job be?

This is another question to get a conversation going. Most of us choose careers that balance talent, need for money, and enjoyment. Sometimes, only one of these factors wins out. But, what job would she choose if she had nothing getting in her way and no obligations?

26. What is your secret guilty pleasure?

Everybody has something they do that brings them great pleasure, but also makes them feel a bit guilty. If she’ll tell you her guilty pleasure, maybe you can help indulge it.

27. Early bird or night owl?

This seems like a simple question, but sleep is a fascinating topic. Most of us don’t get the sleep we should, and we don’t have schedules that truly align with our biorhythms.

So, ask her. Then, you can compare notes to see if your sleep/wake cycles are truly in synch.

Serious Questions to Ask Your Girlfriend

A serious relationship at times requires asking serious questions and most of the time those questions are going to relate to the relationship in some way shape or form. The way your girlfriend may answer these questions is completely dependent on various factors such as cultural or religious beliefs. However they are questions that should be asked at some point or another.

28. Are you friends with your ex?

This is serious in the sense that it makes your girlfriend think about their previous relationships. Ideally, if a relationship ends it’s because both parties realize that neither one is at fault and that it simply isn’t working out. If she is friends with her Ex it’s likely that the relationship ended amicably and that if it is to end between you two that there is still a chance to be somewhat connected.

29. What would you say are your physical boundaries?

When it comes to questions to ask your girlfriend from the beginning this is probably one of the most important. It can help you avoid the most embarrassing moment, or at least one of them, during your relationship with each other. Pay attention to what she says and do not expect to make her like something just because you like it and she says she doesn’t.

30. What did you learn about yourself from your last relationship?

We love this question, but timing is so important. So is tone. This isn’t a good first date question. It’s also a question that might sound as if you are trying to lecture or “school” her. Wait on this question until you’ve hit your third date at least. Then, start by sharing some lessons you’ve learned.

31. How do you know when something is going to turn into a long-term relationship?

Do you have a sign that tells you when a casual situationship is going to turn into an LTR? She probably does too! Use this question to compare notes, and possibly see if things are moving in the direction of true love for the two of you!

32. How do you define success?

You can certainly ask your girlfriend romantic questions, but it’s also good to delve into other areas of her life. After all, she is a whole, complex person with goals and dreams. Learn what being successful means to her. This is a great question that will let you know if you are compatible with her in terms of life goals and accomplishments.

Weird romantic questions

Weird Questions to Ask Your Girlfriend

When you want to have a fun conversation, sometimes you have to move away from serious inquiries and ask weird questions instead. They are usually thought-provoking in ways that you wouldn’t expect. In fact, some of her answers may even become a go to party story for you in the future as your relationship continues.

33. If you woke up tomorrow as your younger self with all the knowledge you had now, what would you do?

This is a fun, what-if question that can really get conversation going on a date. Of course, you shouldn’t ask it unless you have an answer of your own ready to go. Also, there are plenty of variations of this question, so feel free to be creative!

34. What is something that you think you could set a world record for?

Could she set the record for leaving clean clothes in hamper for the longest time before folding them? Maybe she’s shattered the record for reading and rereading her favorite book. Who knows, she may have literally set a world record! You’ll never know unless you ask.

35. Which cartoon character would you be?

Almost all of us grew up watching cartoons, and we all had our favorites. Sometimes, we even engaged in pretend play, fantasizing that we were are favorite cartoon superhero.

Looking back as adults, our perspectives changed. Ask her this fun question and enjoy her responses as you come up with your own. For example, SpongeBob may have been a bubbly, childhood favorite, but Squidward might be the one she relates to most as an adult.

36. What is the worst first impression you ever made?

Who hasn’t been in a situation that just seemed to go wrong from the very start? All you want to do is scream, “I promise, I’m not really like this!”.

Fortunately, these situations are almost always funny looking back, although not in the moment. Why not commiserate with her over this, and get a great conversation going? Always a good idea!

37. Of all the dates you’ve been on, which is was the weirdest?

Weird dates are a universal experience. The good news is that they teach us to laugh at absurd situations, give us really interesting stories to tell in the future. Use this question to encourage her to share one her stories with you!

Intimate Questions to Ask Your Girlfriend

Here, when we say intimate, we’re not talking about her sex life. These are sensitive, personal questions that allow her to open up and discuss things that are meaningful to her. Listen carefully to her answers, and be prepared to field some intimate questions of your own.

38. What was your first kiss like?

This is a simple, sweet question that will give you the opportunity to learn about a special moment in her life.

Related reading: Should You Kiss on the First Date

39. What is the best way to make you feel heard?

Your girlfriend wants you to listen and truly hear what she says when she communicates about important things to her. However, sometimes wires get crossed.

She may think you aren’t truly understanding her when you are absolutely confident that you heard her. Now, the two of you could get caught up in a cycle of arguing over listening, or you can ask her for some simple steps you can take so she knows she is being heard.

40. What was your most vulnerable moment that turned out well?

We all have moments in which we feel extremely vulnerable and exposed. This may happen if we are expected to speak in public or ask someone on a date for the first time. Often, these are experiences that we must plow through even though they are rather painful.

However, there are other times when vulnerability was a big payoff. The speech goes amazingly well, you discover a new talent, or you land a date with someone amazing. This great conversation starter of a question will help you learn more about our girlfriend and the things she has overcome.

Related reading: The Best Flirty Conversation Starters

Important Questions to Ask Your Girlfriend

The final set of questions to start a great conversation that can last for hours.

41. What impact did your parents have on your view of love?

The way she answers this question will reveal a lot about the environment she grew up in. If she is a strong believer in true love, it is most likely that she grew up in a stable and nurturing environment. However, if she seems uncaring or even cynical of romance, it is likely that she did not grow up in a stable and nurturing environment.

42. Do you feel pressured in any way by society just because you are a woman?

Women are under constant pressure to look, dress, and act a certain way as it is what is considered to be appropriate. By getting your girlfriend talking about their stance on this phenomenon, you will not only get a better understanding of her perspective but of the perspective that other women will have as well.

43. What is something that would make you as a girl stop communicating?

This is one of the more important questions to ask. Relationship experts will tell you, communication is so important. Unfortunately, women often find their attempts to communicate frustrating. So, they stop trying.

You may be able to avoid that simply by asking her the things guys say or do that cause women like her to simply shut down.

Related reading: A Guide on How to Be a Better Boyfriend

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Are There Questions You Are Better Off Not Asking?

Depending on the time and place – yes, there are some questions that may feel innocent but are actually taboo to ask. These questions often rely on putting your girlfriend down in terms of her appearance and habits. Or they are completely out of left field and being asked in a place where it is not appropriate to ask. For example, asking her personal questions or even dirty questions in a public area is a complete no. In general, just think carefully before asking.

In some ways, it’s more important to consider the timing of the questions you ask. For example, nobody wants to be hit with an onslaught of questions on the first date. Also, don’t ask your girlfriend random questions, and expect her to respond as if she’s on some quiz show. Just slide in a question or two here or there to start some deep conversation.

Relationships Author
Geoffrey Williams
After taking a required Intro to Psychology course as an undergrad, I have never looked back. Since my doctoral program, I have specialized in adult relationship therapy. Through my studies and clinicals, I wrote several articles for professional journals and currently in the midst of writing a book.

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