Every relationship is built on shared experiences. The date nights, the vacations, the evening video calls while you’re apart. But there’s so much more to discover about each other beneath the surface, and beyond the everyday.

So, how well do you really know your girlfriend? 

While we often focus on daily routines or what’s happening in the moment, deep conversations are where the magic happens. This is where you can discover the entire inner world that makes her who she is—her dreams, passions, memories, and values. It gives you a glimpse into her mind and heart, helping you see the world from her perspective.

Not to mention, asking thoughtful questions is one of the best ways to both understand your girlfriend better and show her how much you truly care about who she is. 

Whether you’re newly dating or in a long-term relationship, there’s always more to discover. These 100 deep question prompts are designed to make sparking meaningful conversation easy while you build emotional intimacy and get closer than ever. 

Going Deep: Why Ask Deep Questions?

You might be wondering—why bother with deep questions? Can’t a great relationship thrive on day-to-day interactions and shared experiences?

While small talk and daily routines have their place, research shows that meaningful conversations can be a strong foundation for deeper emotional bonds. In real life, this translates to fewer arguments, more trust, and a stronger sense of security in your relationship. 

Beyond strengthening your relationship, asking your girlfriend deep questions could even enhance her wellbeing. Studies show that many women tend to process their emotions and experiences through conversation and storytelling. It’s often through sharing thoughts, stories, and feelings that they connect more fully with themselves and others.

By asking these deep questions, you’re doing more than just getting to know her better—you’re creating a space where she feels heard, supported, and valued. You’re showing her that you care about her inner world, her dreams, and her unique perspective on life. 

What can you look forward to when you start asking deep questions?

• Feel More Connected When You’re Apart

  Whether it’s work travel, school, or long-distance, there are times when you and your girlfriend might be physically apart. Staying connected can be a challenge, but asking deep questions helps bridge the gap, keeping you emotionally close even when miles separate you.
  
  As one of our users, Joseph, shared about using deep question prompts with his long-distance girlfriend: “The app just brought us closer man. Like really close dude. We ended up having a hidden love for poetry due to its journalistic nature of the app.”
  
  

• Make Opening Up and Communicating Easier

  Not everyone finds it easy to open up, but deep questions can make those important conversations flow more naturally. By asking thoughtful, open-ended questions, you create a comfortable space for your girlfriend to share her feelings, thoughts, and experiences.
  
  In fact, many couples find that asking deep questions can improve communication when things get tough. Deep question prompts on Waffle gave our user Lamia a way to express herself, and her boyfriend “got to find out how I think and what may bother me, what makes me happy or sad. It helped us communicate on a better level.”
  
  

• It’s a Fun Way to Bond and Grow Closer

  Deep questions don’t always have to be serious. In fact, they can be a fun way to discover new things about each other, share laughter, and even uncover new memories. It’s an enjoyable way to bond, grow closer, and create lasting moments.
  
  James takes a unique approach to using deep questions and the Waffle app: “My wife and I share a journal, used mostly for positive affirmations. We try to leave a comment day about something that we appreciate or like about each other. We also use it to post about meaningful memories and times that we want to remember. The daily questions are great; we sometimes answer those as a way to get to know each other more.This has helped us become closer and feel more cherished by the other.”

Asking Deep Questions: Pro Tips for Curious Partners 

Asking deep questions might sound a little daunting at first, especially if you aren’t sure what or how to ask. But with the right approach and our prompts, they can feel natural, fun, and meaningful. Here are a few tips to help you ease into deeper conversations with your girlfriend:

1. Choose the Right Time

   Timing is everything. Deep conversations flow best when both of you are relaxed and free from distractions. You might want to ask these questions during a cozy night in (or long-distance virtual date), while taking a long walk, or even over a quiet morning coffee. Avoid starting serious conversations when your partner is stressed or overwhelmed. 

   
   

2. Create a Safe Space

   Not everyone finds it easy to open up, and that’s okay. You can help her feel more comfortable by creating an environment that’s calm, open, and supportive. Set the stage for honest conversations by ensuring she knows you’re there to listen without judgment. 

   
   

3. Start with Light Topics

   Jumping straight into the deep end of a conversation can sometimes feel overwhelming. Ease into the more serious questions after starting with lighter, fun questions. This builds comfort and trust. Once you’ve established a relaxed atmosphere, you’ll naturally move into deeper, more personal topics.

   
   

4. Respect Boundaries and Comfort Levels

   It’s important to remember that not every question will be easy for her to answer right away. If she feels uncomfortable or hesitant to respond, respect her boundaries and let her take her time. Deep conversations should feel like a safe space to open up freely, not an interrogation. Give her room to think and reflect—sometimes the most meaningful answers come after time to process.

   
   

5. Share and Reflect Together

   Asking your girlfriend deep questions should feel like a two-way exchange. Once she shares her thoughts, reflect on her answers and offer your own. This back-and-forth creates a dialogue where both of you can grow closer, and she can get to know you better, too!

Deep Questions To Ask Your Girlfriend 

Ready to discover more about your girlfriend? These 100 questions will guide you through meaningful conversations that explore her past, present, and dreams for the future, all while building a stronger connection. Let’s dive in!

1. Hear Her Origin Story: Questions About Childhood & Family

Let’s go back to where it all began. What were the early experiences, people, and memories that helped shape the incredible person she is today? These questions tap into her past, uncovering sweet stories and powerful lessons.

1. What’s your favorite childhood memory and why is it special to you?

2. What’s a childhood dream you’ve never let go of?

3. How would your parents describe you as a kid?

4. What was your favorite holiday you had as a child?

5. If you could revisit any day from your childhood, which one would it be?

6. What’s the best piece of advice you’ve received from a family member?

7. If you could have one of your long-lost childhood toys back, which would it be?

8. What’s a family tradition you’d love to continue or pass on one day?

9. What’s a memory from school that still makes you laugh?

10. If your childhood had a soundtrack, what songs would be on it?

2. Adventure Awaits: Questions About Her Dreams & Aspirations

These questions explore what’s next in her life. What are her big dreams? What keeps her inspired and motivated? Whether she’s working toward a personal goal or dreaming of an epic adventure, these questions will help you cheer her on.

1. What’s something you’d love to accomplish in the next five years?

2. If you could take a year off and do anything, what would you do?

3. What’s one thing you’ve always wanted to learn but haven’t had the chance to yet?

4. If you could design your perfect life, what would it look like?

5. What’s your dream job?

6. What’s something you’d like to cross off your bucket list in the next year?

7. If you had to choose any other profession, what would it be?

8. If you had unlimited resources, what would you create or build?

9. Pretend you’ve been given an empty shop and a million dollars to stock it – what would you sell?

10. If you could live anywhere in the world, where would it be and why?

3. The Heart of It All: Questions About Love & Relationships

From start sign compatibility to love languages, there is no shortage of ways to label how we feel about love. The truth is, we are all unique, and your girlfriend will have her own take on what love really is. Let’s explore what makes her feel valued, how she views love, and what she hopes for in your connection.

1. What’s your favorite way to receive love and affection?

2. What’s the most memorable moment from our relationship so far?

3. How do you feel most supported in our relationship?

4. What’s one thing you’d like us to do more often as a couple?

5. What is your favorite thing about our relationship?

6. What’s your love language, and how do you like to express it?

7. What’s a small thing I do that makes you feel loved?

8. What’s one goal you have for our relationship in the future?

9. How do you envision us growing together over the next few years?

10. What’s the best advice you’ve ever received about love?

4. Through Her Eyes: Deep Questions About How She Sees the World

Ever wish you could spend a day in your girlfriend’s mind? Get a glimpse into how she thinks and what she values most by exploring her beliefs, perspectives, and how she navigates the world around her.

1. What’s a belief or value that’s shaped who you are today?

2. If you could change one thing about the world, what would it be?

3. What’s something you’ve learned recently that changed your perspective on life?

4. Who is your biggest role model?

5. What’s something you believe deeply that others might find unconventional?

6. What do you think makes a person “good” or “bad”?

7. Do you have any regrets in life?

8. What’s something you wish more people understood about you?

9. What’s a cause or issue you’re passionate about supporting?

10. How do you define happiness in your life?

5. Just Between Us: Questions to Deepen Your Emotional Connection

Emotional questions aren’t always easy, but taking time to explore them can be a gateway for even deeper conversations and trust. These questions are designed to bring out vulnerability, helping you both feel more connected by sharing personal thoughts and emotions in a safe, open space.

1. What’s your biggest fear? What is something that scares you but also excites you?

2. How do you handle feelings of loneliness or sadness?

3. What’s one insecurity you’re working on overcoming?

4. To you, what are the signs of a healthy relationship?

5. What’s the hardest thing you’ve ever had to forgive someone for?

6. What is the most important lesson you learned from your last relationship?

7. What’s something you’re still learning about yourself?

8. If you could talk to your high-school self, what relationship advice would you give her?

9. What’s a fear you have about the future?

10. When was the last time you cried, and why?

6. Build Her Bucket List: Questions About Life & Future Plans

Take a look at the bigger picture—her future dreams, life goals, and how she sees the two of you moving forward together. These questions open up conversations about long-term plans.

1. What’s something you hope to look back on in 10 years and feel proud of?

2. How do you see our relationship evolving over the years?

3. What’s your dream for our future together?

4. How do you feel about the idea of marriage or long-term commitment? What do you envision for your dream wedding?

5. If you could design our future home, what would it look like?

6. What’s one thing you want to accomplish before you turn [future age]?

7. How do you imagine balancing work, personal life, and our relationship in the future?

8. What’s one thing you’d love to experience together in the next five years?

9. What’s a big life decision you’re currently thinking about?

10. What’s something you hope we’ll accomplish together as a couple?

7. Inner Reflections: Questions About Personal Growth & Challenges

Help her reflect on her own journey, how she’s grown, and what challenges have shaped her along the way. These questions open up powerful conversations about resilience and self-discovery.

1. What’s a challenge you’ve faced that made you stronger?

2. How have you changed the most in the last year?

3. What’s something you’ve learned about yourself recently?

4. If you could do today over again, what would you change?

5. What’s a personal goal you’ve set for yourself this year?

6. What’s something you’re working on improving in your life?

7. How do you stay motivated when things get tough?

8. What’s a piece of advice you’d give to your younger self?

9. What’s one lesson you’ve learned from failure?

10. How do you celebrate your personal achievements?

8. Spice it Up: Flirty Questions About Love & Affection

Physical affection is a key part of many relationships, and these questions help you explore what makes her feel most comfortable, desired, and loved.

1. What’s your favorite way to be touched or shown affection?

2. How do you feel about PDA, and what level do you feel comfortable with?

3. What’s something you’ve always wanted to try together, but haven’t yet?

4. What’s your favorite type of self-care? How can I pamper you?

5. What’s the most romantic thing we’ve done together so far?

6. What’s your favorite place to spend time together?

7. How do you feel about incorporating surprises into our physical connection?

8. What’s a small gesture I could do that would make you feel appreciated?

9. What’s one thing you’d like to try that could bring us closer physically or emotionally?

10. What’s your idea of a perfect date night? What date ideas should we try next?

9. Let’s Get Silly: Cute Questions for Fun Conversations

Not everything has to be serious! These funny questions let you both unwind, laugh, and enjoy each other’s company while still getting to know her on a deeper level.

1. If you could have dinner with any fictional character, who would it be?

2. If you could re-create our first date, what would we do?

3. If your life were a move, what would the title be?

4. What’s a guilty pleasure movie or TV show you secretly love?

5. If you could live in any era for a week, which one would you choose?

6. What’s your favorite season and why?

7. Are you an early bird or night owl?

8. What’s your weirdest habit that no one knows about?

9. If you could switch lives with anyone for a day, who would it be and why?

10. What’s the silliest argument we’ve ever had?

10. Walk Down Memory Lane: Romantic Questions to Celebrate Your Favorite Moments Together

These questions focus on the beautiful memories you’ve shared together and give you a chance to reminisce about your relationship’s most meaningful moments.

1. What’s your favorite memory of our time together?

2. What did you think the first time you met me?

3. What’s a moment that made you realize you really cared about me?

4. What’s something about our relationship that you never want to forget?

5. What’s your favorite picture of us, and why?

6. What’s the funniest thing we’ve ever done together?

7. What’s a date we’ve been on that you’ll never forget?

8. What’s something I’ve done that made you feel extra special?

9. What’s a memory of us that always makes you smile?

10. How do you want to make more memories together in the future?

Ask Away: Tips for Getting Started 

Starting deep conversations can sometimes feel daunting, no matter how close you are as a couple. The key is to make it fun and natural so both of you feel comfortable and excited about diving deeper. Here are some creative and enjoyable ways to jump into these meaningful conversations:

Tips for Getting Started with Asking Interesting Questions

Sometimes, starting deep conversations can feel a little daunting, but with a few creative ideas, it can become a fun and easy way to bond with your girlfriend. Here are a few tips to make it feel natural:

Create a Mystery Question Jar

Can’t decide which question to pick first? Turn it into a game by writing your favorite questions on slips of paper and putting them in a jar. Whenever you’re hanging out, pull a random question and take turns answering. It adds a touch of surprise and makes the conversation feel spontaneous and playful!

Use a Conversation Starter Game

One hundred questions sounds like a lot, but if you make a habit out of asking deep questions, you’ll likely find yourself looking for new inspiration eventually. Thankfully, there are many board games and card decks designed specifically for couples to focus on relationship-building questions like these. Look for games like We're Not Really Strangers, The And or Actually Curious which can turn a simple conversation into game-night. 

Find More Prompts on the Waffle App 

Waffle was created to help couples just like you connect more deeply through thoughtful daily prompts. With a wide variety of questions designed to spark meaningful conversations – just like these! – the app makes it easy to add deep. 

Each day, the app offers a new prompt that you can answer whenever it feels right. You can choose to respond on your own or make it part of your daily ritual together, like discussing your answers during dinner or sending a sweet message before bed. conversations into your everyday routine without it feeling forced.

“I use Waffle with my long distance girlfriend,” shares Waffle user, Angel. “We use it to document our days, so that even when we don’t get to talk much, we have entries to go over and look at. It helps us keep up with day to day experiences we are having while being so far apart.”

Waffle isn’t just for girlfriends, boyfriends, or long-distance relationships. You can even use it to ask many of these same deep questions to your siblings, children, best friends, or use it as a personal journal to get to know yourself better. 

Get Inspired and Connect Deeply with Waffle  

Are you ready to bring more curiosity and meaning into your daily chats and date nights? Deep questions have the power to not only make your conversations more interesting, but help you and your girlfriend grow closer than ever. So go ahead—start asking, stay curious, and enjoy the journey of discovering more about the incredible person you’re with. Download the Waffle app today and send your first question prompt!