54 Intimate, Deep Questions to Ask Your Girlfriend & Make Her Feel Understood

If you want to get to know your girlfriend in an intimate way, here are deep questions to ask your girlfriend to get to know her better and strengthen your relationship.

If you want to bond and connect with your lady, you’re going to need to keep these deep questions to ask your girlfriend in mind. You can’t just ask her how her day was. And she needs to do more than tell you her favorite flavor of ice cream!

Getting to know your girlfriend

You might be wondering why it’s important to get to know your girlfriend on a deep level. After all, it’s just easier to talk about the weather or things you like, such as video games or sports.

But for a relationship to be strong and healthy, you need to open up to each other and become vulnerable. When you learn personal things about someone, you immediately become closer to them. 

That’s what romantic relationships are all about. Becoming emotionally connected to each other will build a strong foundation for the future of your relationship. And if you skip asking these questions, then you are missing out on the opportunity to grow your partnership and take it to the next level.

So, if you want to really connect, you need some deep questions to ask your girlfriend. [Read: How to learn to be more vulnerable and open in your relationship]

How to start a deep conversation with your girlfriend

You might not be the most talkative guy or even a deep thinker, so you might not even know where to begin to start a meaningful conversation with your girlfriend. Don’t worry, that’s why we’re here!

If you’re apprehensive about it, don’t be. It’s really not that difficult to start a deep conversation. It all really just starts with asking her questions. That’s the easy part. All you have to do is throw out some of these questions, and it will automatically get her talking. 

Learning more about her doesn’t have to look like an interview either. You can ask a question here or there, while you’re driving or in bed cuddling. You don’t need to sit down with her at the table and have a serious discussion. [Read: How to make your girlfriend feel loved with the right questions]

The great thing is that if the conversation ever has a lull and you can’t think about what to talk about, just throw a few of these questions out to her, and the two of you will be able to talk forever.

Deep questions to ask your girlfriend

When first dating someone, we spend most of our time worrying about what they think and hoping we don’t screw it up. You want this person to like you and want to spend time with you.

But what happens after dating, when you’ve passed through all the small talk, and you already know all the basics about her? [Read: 50 Warm, feel-good questions to ask a girl to get to know her better]

The key to a healthy relationship is just not talking about your day. There needs to be something more – something that differentiates casual sex from a serious relationship.

According to relationship experts, asking questions is the best way to know your partner better. However, you should be careful. If she feels like you’re prying, there is a chance that she might close up if she’s not comfortable with self-disclosure. So, you should open up as well and be honest with her. You probably want to do this by now, but you’re still not sure what questions you should ask her. 

Well, don’t worry, we have you covered. Here are some of the best deep and meaningful questions to get to know your girlfriend better, either as conversation starters or when you run out of things to talk about. These questions are great to ask no matter how long you’ve been together. [Read: 40 Open-ended, serious questions to ask a girl and get her to open up]

Let’s get deep deep.

1. What is your deepest fear? 

It’s a personal question, and once you know what her deepest fear is, you’ll be able to understand her that much better. 

Many of our actions are connected to our fears, so, by knowing what scares her, you’ll be able to see why she does the things she does. It’ll also give your girlfriend a chance to let you know how you can support her through her fears.

2. If you imagine yourself in twenty years, what do you see? 

Now, this will take some visualization on her part. No one really likes this question, but it shows you a lot of who they are. Does she see herself traveling, having a family, working, or all three? [Read: 14 steps to emotionally connect with someone and feel closer]

Plus, it gives you a glimpse of whether or not she can see you in your future and vice versa. If she’s interested in traveling and you’re not, well, that may be a problem.

3. Are you a spiritual person? 

This is an important deep question to ask your girlfriend. Whether spirituality is important to you or not isn’t necessarily important.

What’s important is if you are able to respect each other’s beliefs. If you’re not spiritual and she is, you’re going to have to either accept it or move on.

4. What did you want to be when you were five years old? 

We all had that one big dream of what we wanted to be when we were five years old. We were free to imagine crazy and wild dreams in our heads. As her partner, find out what those dreams and aspirations were. [Read: Love or career – how to choose and make sure you’re not left feeling bitter]

Let her bask in it when she’s telling you and see if there’s some way you can help her make those dreams come true, even in the smallest of ways. This could also be quite a cute question to ask your partner as you’ll get to know how she was as a child.

5. In moments when you’re feeling uncomfortable, is there something I can do to better support you? 

No one knows how to react when their partner is going through a hard time. What can you do? Pat her on the shoulder and tell her it’s going to be okay? 

Usually, that’s not enough. Yet, we never ask our partners what we can do to better support them. Ask her this question and she’ll tell you exactly what she needs from you during tough moments. [Read: 15 thoughtful ways to comfort a girl and do it right]

6. What’s a hard lesson you had to learn in life? 

Life isn’t easy nor is it always fun. We all experience hard days, days of pain, and moments that we wish would just end already. But those days make you a stronger person and teach you a lot about yourself. 

What were her struggles and how have they changed her into the person she is today? You never know, maybe she never learned from her mistakes. Nevertheless, asking interesting questions like this will help you get to know your girlfriend on a deeper level, especially if you’re planning on a long-term relationship.

7. What is your relationship like with your father?

I know this sounds like a weird question, but it’s extremely important. So many women have poor relationships with their fathers which alters the way they see men. [Read: The effects of a good or a bad father on a girl]

Now, this isn’t a deal breaker, but it’s important to ask as this question will give you an idea of how she views men. It will also show you any forthcoming issues that may occur.

8. Have you ever loved someone before? 

We’re not including friends and family in this one. When we say love, we mean it in an intimate sense. 

Love is an essential part of the human experience and of course, you want to know if she’s experienced these feelings before.

If she’s been unable to love others, then it may be a problem in your relationship; it means she’ll struggle opening up to you. [Read: Retroactive jealousy – why is your lover’s past making you jealous?]

9. Is there something you stopped doing even though you loved it? 

We all have loved things that we sadly stopped doing. For whatever reason, our dreams and interests get shoved to the side. 

What were her dreams and desires? Find out if she stopped doing some of the things she loved and why. This question is perfect as you can then surprise her by doing the activity together!

10. What’s one of your favorite memories? 

Even if her childhood was horrible, there’ll be at least one positive childhood memory. It doesn’t have to be extravagant, but it’s a memory that’s stuck with her throughout her life. [Read: What is pillow talk and how to use it to perfect your romance]

If you want to connect in a positive way, asking her about her favorite memory is a great way to do it. It will give you both a special moment where she’s remembering what made her happy.

11. How do you feel about our sex? 

When it comes to the list of questions to ask your girlfriend, this question may not be the most comfortable one. However, it’s an important question to ask. Talking about this will help you get to know if you’re satisfying her in bed.

Sex is absolutely a crucial part of a relationship and you should always check to see that you and your partner are on the same page.

Maybe she’d like more or less sex, or even to switch things up in the bedroom. But you won’t know unless you ask your girlfriend questions like this. [Read: 13 clear signs she really enjoys having sex with you]

12. Is there something in I’ve done in the past week that may have unintentionally hurt you? 

Listen, we all say or do things that may hurt our partners unknowingly, but that doesn’t make us bad people. You’re probably not even aware of what you said or did. However, she’s keeping her feelings locked inside, and you don’t want that to end in an explosion.

Asking if you’ve hurt her in the past few days will help you understand the things you do which negatively affect her. [Read: 21 things you do that hurt your girlfriend’s feelings]

13. Do you feel dissatisfied about an argument we’ve had in the past week? 

Couples argue. That’s just the way it is. Now, you should aim to ask her just about this past week, because if you keep it too broad, she’s going to go way back – and we want don’t want to reopen old wounds.

You may not want to ask this question, because you think she’ll get mad at you. But working through these issues to improve your relationship makes a really big difference to your future.

Don’t ignore your issues, face them with her. [Read: Follow these steps to forge a deeper connection in your relationship]

14. What are you looking for in our relationship? 

We know you’re in a relationship with her, but what is she looking for in a relationship? What does she want from her partner and vice versa? 

There are probably some things that you both need to work on, yet you don’t know what they are. This is an important deep question to ask your girlfriend.

15. How do you best receive love?

It’s a fact that every relationship needs romance. The thing is, you may interpret love through hugging and kissing, but she may interpret it through cooking and cleaning. Do you get it? [Read: How to make your girlfriend feel loved and needed]

Not everyone receives and gives love in the same way. This question will help you understand how she gives and receives love. That way, you’re on the same page.

16. Where do you see yourself living? 

Well, you may love the city, but she loves the countryside. Sure, it sounds stupid, but it’s something you need to ask her. 

If you’re never planning on leaving your town, but she wants to travel the world, then you’re going to have a problem taking the relationship to the next level. [Read: 9 Reasons traveling is a great test of compatibility]

17. When you’re struggling to speak with me about a difficult topic, how can I support you? 

Talking to your partner about a hard topic isn’t easy and takes a lot of courage. She may not feel completely comfortable talking to you about these things, but that means you need to step up. You need to ask her how you can support her during those moments.

18. How am I as a partner? 

This is one of those intimate questions to ask your girlfriend that’ll actually improve your intimacy with her. No one wants to hear criticism, but could you be a better partner? Is there something missing? 

If so, this could be why she may not be opening up to you, for example. Ask this question and expect an answer. [Read: These are the traits to being a good boyfriend]

19. How do you feel about marriage and children? 

You may be thinking it’s a little soon, but honestly, it’s never too soon *except maybe on the first date*. But really, this is something to ask. 

If you’re not someone who wants children and she does, then there’s no point in even dating. You’re wasting each other’s time. Get this topic out of the way because it can be a deal breaker.

20. Why do you think your previous relationship didn’t work out? 

Yes, it’s an awkward question, but this question will reveal so many things. First of all, you’ll see the type of people she attracts and why. [Read: 20 racy ways to spice up monogamous sex when it gets boring]

Secondly, you’ll see why they broke up. What happened? Though you’re only hearing it from her side, you’ll be able to put the puzzle together. This is a good deep question to ask your girlfriend.

21. Have you ever cheated on a partner? 

This is an important question and one that may not bring out the answer you were looking for. You want a partner that you can trust, and if they’ve chronically cheated on people in the past, well, it’s not looking good for you.

22. Are you being who you want to be? 

This is really a hard and personal question to ask someone; you’re basically asking her if she’s happy with who she is, and if she’s achieved what she always dreamed of.

But this also shows you what she thinks of herself, and how she sees herself. [Read: These are the questions to ask to know if they are the one]

23. What kind of parent do you think you’ll be? 

Usually, we pick and choose our parenting skills from our own parents. Now, you may not even be thinking of having kids, but this question will show you how she was raised. She may want to be a “cool” mom because her own parents were very strict.

24. How important is sex for you? 

Well, you may be highly active, but she may not see sex as something important. This doesn’t mean you need to cut things off, but it does show you her thoughts about physical intimacy.

25. Right now, do you need more space or less space from me? 

Even though being in love is an amazing feeling, we all need our own space from time to time. [Read: 23 things girls wish guys knew about a girl’s mind]

Does your girlfriend need more space from you or less? Is she feeling she’s not getting enough intimacy from you or is she feeling slightly suffocated?

This question shows her that you’re not with her to suffocate or ignore her; you want to find a healthy balance.

26. What is the best way for me to tell you that I am out of balance?

Everyone has stress in their lives – it’s just normal. Some people handle it better than others, but some people can get out of balance sometimes. If that sounds like you, then ask her how to tell her that. [Read: How to reduce stress – 17 fastest hacks to a calmer and happier life]

Some guys aren’t very communicative about vulnerabilities like this, so this might be difficult. But it’s good to have open communication with each other and your girlfriend will appreciate that you asked deep questions like this.

27. What do you do to take care of yourself?

Now, you have to tread lightly on this question. If she’s overweight or doesn’t have a good self-image, she might get defensive and think that you are telling her to lose weight or get healthier.

So instead, you might want to be more specific and ask her if she gets massages, takes bubble baths, or reads books to relax.

That way, she won’t take any offense to “taking care of herself” because you’re asking her about taking care of herself mentally and emotionally, not necessarily just physically. [Read: How to take care of yourself emotionally and avoid falling apart]

28. What worked well in your previous relationships?

Maybe your girlfriend isn’t a morning person, but you are and you don’t understand why she doesn’t like to talk in the mornings. She might tell you that she and her previous boyfriends just agreed to no morning sex and didn’t talk until noon.

Or perhaps she liked how her previous boyfriends texted her every day because she likes to keep in close contact. Whatever it is, ask her what she likes and what has worked for her in previous relationships.

29. What do you like the most about yourself?

This is a great question to ask because it forces her to look at herself in a positive way. As you probably know, a lot of girls are insecure and only focus on what they don’t like about themselves. [Read: How to be yourself – 26 steps to unfake your life and love being you]

If she can’t come up with anything, then go ahead and tell her what you like the most about her. Even if she does tell you what she likes about herself, you should still chime in and tell her what you think her good qualities are. Girls always love to hear that.

30. Do you think that we could lead a long, happy life together?

Your girlfriend will most likely be thrilled to hear you ask this question. Most girls think about the future with their boyfriends, and the fact that you are too will make her really happy.

However, if you’re still not sure about what your future holds with her, then you should probably avoid this question. It might give her false hope and she might think that you want to get married.

Maybe you do, maybe you don’t. So, just be careful if you decide to ask this one. [Read: 50 Questions for a new relationship to predict your romantic future]

31. How have I changed since we started dating? 

This is a tricky one too because you have to be ready to hear the truth. If you think you have gotten lazy in the relationship or in life in general, then she might tell you that. Not that you shouldn’t make positive changes, but be prepared for what she says.

Hopefully, you’ve changed for the better. And hopefully, she has too. So, this is a great question to ask in that situation. 

32. Do we communicate well?

Unfortunately, we are not taught how to be good communicators. Because of that, a lot of people are bad at it. Many people can’t control their emotions well enough to have a rational conversation to work out problems. [Read: How to communicate in a relationship – 16 steps to a better love]

So, if either one of you falls into this category, then it’s a good question to ask your girlfriend so you both can try to learn to become better communicators. After all, communication is the glue that holds strong relationships together – but can also tear them apart.

“What if” questions to ask your girlfriend

Here’s a different twist on deep and interesting questions to ask your girlfriend. If you want to “test” her, your compatibility, her feelings for you, or your relationship as a whole, then these fun questions will help you with that. Not only that, but you’ll also get the conversation flowing with these “what ifs.”

Our list of “what if” questions below covers both sides of the humor spectrum, with suggested “Good,” “Neutral” and “Bad” responses ranging from the lovable to the frighteningly funny. [Read: 177 fun random questions to ask a girl and make her enjoy your company]

Deep and fun questions to ask your partner starting with “What if”

Not all questions have to be serious! The key point here is knowing what questions to ask your girlfriend over text or maybe while you dine out at a romantic place.

Irrespective of making her laugh, however, there are some very good points to be taken away from the kind of responses you can expect to get. If those responses are mainly “Good,” then it sounds like you’re dating a perfect angel. 

Getting a majority of “Neutral” answers probably means you’re dating a more practical woman, someone who no doubt loves you, but also has an eye on the bigger picture. 

If her answers are more along the “Bad” lines, then reading some of the example responses below should make you realize exactly what kind of a person you’re dealing with. [Read: 196 fun and deep relationship questions to test your couple compatibility]

1. What if you could teleport, Star Trek style, to anywhere in the world?

Good answer: I’d teleport to the bedroom and take you with me.

Neutral answer: I’d probably take us somewhere nice and relaxing where we could get some quality time together.

Bad answer: I’d teleport anywhere that would take me away from your sh*t!

[Read: 8 tips to have a great time when you travel as a couple]

2. What if you could go back in time?

Good answer: I’d go back to when you were younger, and watch you go along every step of your life to become the man you are now.

Neutral answer: I’d go back to when we first met and laugh at how awkward we were.

Bad answer: I’d go back to when you were conceived and persuade your father to wear a condom.

3. What if the world were about to end?

Good answer: I wouldn’t care as long as I was with you.

Neutral answer: I’d probably pray for forgiveness and take a little time to think about everyone I’ve ever met who’s ever meant anything to me.

Bad answer: I’d thank my lucky stars I was finally getting away from you.

4.  What if your parents didn’t like me? Would you rather be with me or obey them?

Good answer: I wouldn’t care. If they didn’t like you, then I wouldn’t want to see them much anymore.

Neutral answer: It would be really difficult, but we’d just have to work something out.

Bad answer: What do you mean by “if”?

[Read: Meeting your girlfriend’s parents: 21 dos and don’ts]

5. What if my brother hit on you?

Good answer: He wouldn’t dare. He knows how much I love you.

Neutral answer: I wouldn’t know what to say. I think I’d just be embarrassed.

Bad answer: I’d probably just f*** him again.

[Read: Should you ever forgive a cheating partner?]

6. What if I liked to dance naked while listening to One Direction?

Good answer: I’d have you certified.

Neutral answer: Errrrm, I’d be a bit weirded out.

Bad answer: Sounds delightful. Can I join in next time?

7. What if I had no money… would you still love me?

Good answer: I’ve never thought about your money for a moment.

Neutral answer: It depends on how you lost it.

Bad answer: Nope.

[Read: 11 signs you’re being used for sex or money]

8. What if we were stuck in an elevator?

Good answer: Sounds like a perfect excuse for a bit of romance.

Neutral answer: I wouldn’t really like that. I’m scared of confined spaces.

Bad answer: I’d throw myself down the lift shaft rather than stay there with you!

9. What if I asked you to move in with me?

Good answer: I’m already there, my love.

Neutral answer: I’d need some time to think about that.

Bad answer: Sure! Right when the devil comes skating over hell with a blue moon under his arm and a pack of flying pigs pulling his sleigh.

[Read: The 8 big cons of moving in no one wants to talk about]

10. What if I only had one month to live?

Good answer: I’d be devastated. I’d want to live a lifetime with you in those thirty days.

Neutral answer: It would be really difficult emotionally, but we’d still have to think about getting our affairs in order.

Bad answer: I just hope it’d be in February.

11. What if you fell out of love with me?

Good answer: That would never happen, darling.

Neutral answer: I hope we’d be mature enough to talk about it like adults.

Bad answer: Dude… that happened the day before I’d even met you.

[Read: 12 signs you’re starting to fall out of love with your partner]

12. What if I got amnesia?

Good answer: I’d remind you of all the beautiful things we’ve done together and nurse you back to full health.

Neutral answer: I’d make sure you got the best help our health plan could afford.

Bad answer: I’d pretend I was your cleaner and hand in my notice.

13. What if I went to prison?

Good answer: I’d be there waiting for you at the end of it, no matter what you’d done.

Neutral answer: I don’t know, darling. It all depends on why you went.

Bad answer: I’d be aiding the prosecution.

14. What if you were pregnant?

Good answer: It would make me the happiest woman on earth.

Neutral answer: Things would be tight financially, but I’m sure we could manage.

Bad answer: It depends on whose baby it was.

[Read: 11 ways to know if both of you are ready to have a baby!]

15. What if you were stranded on a desert island with me, but we had no food?

Good answer: I’d learn how to fish so I could cook for you every day, and we could live together in tropical bliss.

Neutral answer: I guess we’d have to work out some way of getting off the island before we starved.

Bad answer: I reckon I could live off you for at least a fortnight.

16. What if I got really fat?

Good answer: I wouldn’t care. It’s the person inside who I love.

Neutral answer: I’d probably try and help you lose some of it before your health suffered.

Bad answer: You couldn’t repulse me any more than you already do.

[Read: Should I speak up about my partner gaining weight?]

17. What if I had a twin brother?

Good answer: That would be wonderful for you. Another close person in your life with whom you could share things.

Neutral answer: That would be nice as long as he’s not over here ALL the time.

Bad answer: Yes! Double the fun!

18. What if you found out I used to be a girl?

Good answer: I’d love you for who you are, not what you were.

Neutral answer: I’d want to know why you’d never told me that before.

Bad answer: Well, that would sure explain why you have no balls.

[Read: The different genders and why you really need to know them]

After you ask these questions – what to do next

Now that you know all the deep questions to ask your girlfriend, you need to know what to do during the conversations. Here are some tips you should follow.

1. Open up and share information about yourself too

You can’t just make your deep conversation all about her. Sure, you want to really get to know her better. And she might even like talking about herself. But the best way to get to the depths of her thoughts and deepen the conversation is to open up too.

It may or may not be easy for you to do this, but it has to be a two-way street to keep the conversation flowing. Emotional intimacy is built by two people sharing themselves, not just one. So do your best to share anything she asks of you too. [Read: 19 Secrets to open up to someone you’re dating even if you’re scared]

2. Remain calm

As we mentioned in some of the questions, you might hear some of her answers might not be what you want to hear. For example, if you ask about her previous relationships, you might get uncomfortable hearing about her ex-boyfriends.

Or if you ask about your sex life, she might give you tips on how you can do better in the bedroom. No one wants to hear that, but you have to remain calm. She’s not criticizing you, she’s hoping for lasting relationship growth. Getting the answer to these questions can help you know more about your girlfriend and help strengthen your relationship.

3. Never react in a judgmental way to a response

It’s easy for people to have a knee-jerk emotional reaction to things people say. And as a result, they can also come across as judgmental. But the last thing you want to do is get your girlfriend offended. [Read: How to be less critical – 15 reasons why you judge and how to stop it]

Instead, you need to make her feel safe talking to you. Even if you really are judging her in your head, keep it to yourself. She needs to know that you love and accept her for exactly who she is.

4. Make sure you never push her into sharing information

Maybe she is the one who is a bit uncomfortable sharing personal information. And that’s okay because everyone is different. Even when you think everything on this list are great conversation starters that you want to ask your girlfriend, you still need to read her body language to make sure she feels good telling you things.

Don’t ever push her to talk about anything when your conversation starts to get serious. Even if she starts to tell you but hesitates, you can stop her and tell her she doesn’t have to share if she doesn’t want to. Ask follow up questions to spark further conversation, too. Lastly, be mindful of the right time to ask these questions. You wouldn’t like your partner to feel like you’re just prying on her personal life out of the blue.

[Read: 60 get-to-know-you questions for a new romance]

You’re not going to remember all the deep questions to ask your girlfriend in one go, but you are going to remember the ones that matter to you. So, ask away, and the truth will be revealed to you.