By

By

By

Kaitlan Downes

on

on

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Jun 21, 2024

Jun 21, 2024

Jun 21, 2024

100 Deep Questions to Ask Your Boyfriend

100 Deep Questions to Ask Your Boyfriend

100 Deep Questions to Ask Your Boyfriend

How well do you really know your boyfriend?

The truth is, we’re all complex, layered people with deep lives and even deeper thoughts. You may never know your boyfriend like you know yourself, but you can get close. Asking deep questions to get to know someone is one of the best ways to see the world from their eyes and communicate with them better. 

So, what are some deep questions to ask your boyfriend?

There are thousands of questions to ask and countless conversations waiting ahead of you. But for now, let’s get inspired with these 100 deep questions and shared journal prompts

Why Ask Questions?

Before we dive into the questions, you might be wondering, why bother with these deep questions anyway? 

Deep conversations aren’t just for therapy sessions or serious talks. These questions can become your secret weapon for building a stronger, more intimate relationship. Here’s why they’re so important:

  • Feel More Connected When You’re Apart
    Work travel, deployment, and long-distance relationships can keep you and your boyfriend miles apart. Staying connected across the distance can be challenging, but deep questions like the prompts in the Waffle app help bridge the gap.


    “I use it [Waffle] nearly every day with my long distance boyfriend,” says our user Nova. “We like to answer the daily prompts so we can learn more about each other. I'd say it's made myself and my partner feel much closer to each other. The questions asked are genuine and interesting, and not necessarily something I'd think to ask him on my own. I'm always looking forward to seeing his answers and learning more about the way he thinks. He's said the same of my answers, too...It makes us feel so much more connected.”

  • Make Opening Up and Communicating Easier
    Let’s face it, not everyone is great at expressing their feelings. Deep questions provide a comfortable way to ease into those important conversations, making it easier to open up and communicate effectively.

    Jake and his girlfriend found that taking time to ask deep questions didn’t just strengthen their relationship – it saved it. “In some ways, Waffle played a big role in saving our relationship. My girlfriend and I had been friends for over a year before we started dating, so once we hit a pretty rough patch about a month in, I was scared that I'd not only lose my girlfriend, but my best friend also. The problems we were facing mostly had to do with a lack of communication, and I was ultimately drawn to Waffle because of its daily prompts – which I thought would help us get to know each other better by finding new things to talk about.”

  • It’s a Fun Way to Bond and Grow Closer
    Who says deep conversations have to be heavy? Asking these questions can be a fun and engaging way to bond, laugh, grow closer, and even discover new sides to each other. Our user James and his girlfriend used deep question prompts in Waffle as a way to capture memories: “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. This has helped us become closer and feel more cherished by the other.” 

The Art of Conversation: Tips for Asking Questions 

Getting to know anyone – including your boyfriend – is a bit like a treasure hunt. Perhaps you have an idea of what kind of treasure you’re looking for, or where you might start searching. But where ‘X’ marks the spot is just the surface. You have to dig deep to get to the real treasure, and you might be surprised by what you find! 

Just like a treasure hunt, searching for more meaning in your relationship may lead you down paths you never expected to find rewards you never imagined. Truly getting to know someone goes beyond scratching the surface—it requires digging deeper into their thoughts, memories, and opinions to explore who they really are. But deep conversations aren’t always easy. 

Here are some tips to help you become a master at asking deep questions:

  • Choose the Right Time
    Timing is everything. Select moments when both of you are relaxed and free from distractions. Ideal times might include a quiet evening at home, a leisurely weekend morning, or during a long walk. Avoid bringing up deep questions during stressful or busy times. The Waffle Journal app makes this part effortless. Simply send your question or prompt and your boyfriend can choose when they feel ready to respond.

  • Create a Safe Space
    Not everyone likes to wear their heart on their sleeve. Many of us need time or a certain environment to feel ready to share. You can help put them at ease by setting the stage for an open and compassionate conversation. Try a cozy, intimate setting, like a candlelit dinner or a quiet park, where you both can feel free to open up.

  • Start with Light Topics
    Want to ask some deep questions on your next date or through the Waffle Journal app? Take it slow. Rather than jump head first into the serious questions, ease in with a few lighter, fun topics first. This will build comfort and trust and may open some interesting doors for conversation.

  • Respect Boundaries and Comfort Levels
    If your boyfriend seems uncomfortable or hesitant to answer a question, that’s okay. It’s more important to respect his boundaries  than get an answer – after all, the whole point is to grow closer, not push someone away. Not every question needs to be answered immediately, and time to process and reflect can lead to even more meaningful conversations later on.

  • Share and Reflect Together
    Asking your boyfriend deep romantic questions should feel like a mutual exchange, rather than an interrogation. After he’s answered, reflect on what he shared and offer your own thoughts and feelings on the topic. 

Deep Questions To Ask Your Boyfriend  

Ready to dive in? Asking your boyfriend deep questions is one of the best ways to really get to know him. The questions in this set go far beyond everyday chit-chat and “how was your day?” We’re going to swing open the door to understanding his innermost thoughts, dreams, and values, all while making him feel heard and loved. 

Inner Child Playdate: Questions to Ask About Their Family & Past 

Ever wondered what your boyfriend was like as a kid? Would you have been fast friends on the playground? Reminiscing on childhood stories is not only a great way to understand what shaped your boyfriend, but invites his inner child out to play. Get ready to dive into tales of family traditions, childhood dreams, and those adorable little quirks that make him who he is today.

  1. What is your fondest childhood memory?

  2. What was your relationship like with your parents growing up?

  3. What’s your weirdest family tradition?

  4. What’s the most valuable lesson you learned from your childhood?

  5. Who were you closest to in your family and why?

  6. What were you exceptionally good at as a kid?

  7. What toy from your childhood would you love to play with again?

  8. What was your favorite family vacation?

  9. What’s a childhood fear that you’ve overcome?

  10. Which childhood friend would you love to reconnect with most?

Co-Create a Dream Future: Questions to Ask About Their Aspirations

We’ve talked about the past, now let’s dream about the future! These questions are your ticket to exploring your boyfriend's biggest goals and wildest ambitions. Whether he's dreaming of starting his own business, going on an adventure, or mastering a new skill, this is your chance to cheer him on and maybe even plan some dreams together. Let’s map out an exciting future…

  1. What is your biggest dream or goal in life?

  2. What would you like to be different about your life in one year? What about five years?

  3. What motivates you most to reach your goals?

  4. What’s a career milestone you’re most proud of?

  5. What personal skills or traits are you working on improving?

  6. If you could wake up tomorrow in a different place, where would you like to be?

  7. If you could own a business, what would it be?

  8. How would you spend 10 million dollars?

  9. What is something you’ve always wanted to try but haven’t yet?

  10. How do you envision our future together? Where do we live? What do we do for fun?

Take the High Road: Questions to Explore Their Values & Beliefs 

We all live according to a different set of values, morals, and ethics. What seems black and white to you may be gray matter for your boyfriend, or vice versa. Asking these deep questions about your values is one of the best ways to better understand how your boyfriend thinks about the world and may even help you both gain a wider perspective. 

  1. What three values do you think “good people” have in common?

  2. How do you define success?

  3. What moral dilemma are you stumped by?

  4. What causes or issues are you passionate about?

  5. Is it better to be honest or kind? 

  6. What do you believe is the key to a fulfilling life?

  7. How important is spirituality or religion to you?

  8. What’s a belief you hold that might be considered unconventional?

  9. What is something you do (or don’t do) that feels “off-brand” for you?

  10. What’s the biggest misconception people have about you/

Nurture Your Love: Deep Questions to Ask Your Boyfriend About Your Relationship

We’ve asked deep questions to get to know your boyfriend, so now let’s go deep into your relationship. Talking about your relationship is something many couples put off until frustration and irritation builds into an argument. Not you! Let’s dig into what's working, what could use a little TLC, and how you can grow stronger together. Get ready to chat about love languages, favorite memories, and ways to keep the romance alive. 

  1. What do you like most about our relationship?

  2. When do you feel most loved and appreciated by me?

  3. What’s your love language? 

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

  5. What’s your favorite memory of us?

  6. What do you remember most about our first date?

  7. What’s your favorite way to spend quality time together?

  8. How do you feel we can improve our communication?

  9. What’s a challenge we’ve faced together that made us stronger?

  10. How do you like to be supported during tough times?

Between the Sheets: Questions to Ask About Sex & Intimacy 

Intimacy (in whatever form that takes for you) is a necessary part of any healthy, fun, rewarding relationship. But, being open and vocal about what we want with sex and intimacy can be a touchy subject. These deep romantic questions can help set the mood for a deeper physical and emotional connection, whether you're looking to explore new fantasies or understand each other's boundaries better.

  1. What about me turns you on the most?

  2. What are your boundaries when it comes to physical intimacy?

  3. How can we improve our sexual connection?

  4. What’s something new you’d like to try together?

  5. What’s your favorite way to be touched? 

  6. What sexual frequency feels right for you?

  7. How do you feel about PDA?

  8. What’s your favorite memory of an intimate moment we’ve shared?

  9. How do you feel about incorporating toys or accessories into our sex life?

  10. What can I do to make you feel more comfortable during intimate moments?

Dive into the Deep End: Questions to Embrace Vulnerability 

Embracing vulnerability can feel scary at first, but actually helps you strengthen your bond and build a foundation of trust. Let's dive into the deep end and get real with each other.

  1. What’s your biggest fear in life?

  2. Is there anything about our relationship that scares or tests you?

  3. What’s a personal insecurity you struggle with?

  4. When is failure a good thing?

  5. What’s a difficult experience that has shaped who you are today?

  6. How often do you feel lonely? How do you handle feelings of loneliness?

  7. What’s something you’ve never told anyone before?

  8. How do you process and express emotions?

  9. What’s a regret you have, and what did you learn from it?

  10. What’s a dream or goal you’re afraid to pursue?

The Big Stuff: Important Questions to Ask Your Boyfriend 

Are you and your boyfriend on the same page about big issues and long-term plans? From commitment and kids to finances and family dynamics, these questions help you break the ice on some more challenging big-picture conversations to gauge your lifetime compatibility. 

  1. How do you define a successful relationship?

  2. Do you see yourself getting married (or a similar commitment) one day?

  3. What are your “deal-breakers” for a long-term committed relationship?

  4. Do you envision a life with children? If so, how would you want to raise them?

  5. How do you think we should manage finances in our relationship?

  6. How do you handle major life decisions?

  7. What are some relationship goals you have for us?

  8. If we had a major conflict, what would you do to show forgiveness? What would you expect me to do to show you forgiveness?

  9. Do you think any relationship could survive infidelity or cheating?

  10. What obstacles do you foresee us overcoming in our long-term relationship?

Light & Fun Questions to Ask Your Boyfriend 

Whew, that’s deep. Now, let’s shift the conversation to something a little lighter. Not all conversations need to be deep and serious to be meaningful. In fact, lighthearted questions can open up some really interesting aspects of your boyfriend and your relationship together. Plus, they add a touch of fun and whimsy while you bond. Ask these questions for a casual or quirky convo or to clear the air after a disagreement or deep dive. 

Your Life is a Movie: Questions to Put Your Boyfriend Center Stage 

Let’s bring some main character energy to this conversation. Whether you’re planning your imaginary superhero abilities or designing your dream house, these questions are all about having fun and seeing where your imagination takes you.

  1. If your life were a movie, what genre would it be?

  2. Who would play you in a movie about your life?

  3. If you could live in any fictional world, which one would you choose?

  4. What would the title of your autobiography be?

  5. If you could have any superpower, what would it be and why?

  6. You’re the main character of a movie, sitting in the back of a taxi and looking longingly out the window as you drive through the rain. Where are you going?

  7. If you could have dinner with any three people, dead or alive, who would they be?

  8. What’s a skill you wish you could master instantly?

  9. If you could time travel, where and when would you go?

  10. What’s a crazy invention idea you have?

Felt Cute: Flirty Questions to Ask Your Boyfriend

Let’s make your boyfriend blush. These questions are perfect for date nights or cozy moments, or whenever you want to remind yourselves why you’re so smitten with each other.

  1. What’s your favorite physical feature of mine?

  2. What do you think makes our relationship unique?

  3. What city best represents our relationship and why?

  4. What’s your favorite thing to do together?

  5. What’s a nickname you love being called by me?

  6. What’s the most romantic thing you’ve ever done? What’s the most romantic thing I’ve ever done for you?

  7. What’s a song that reminds you of us?

  8. If we made it into the Guiness Book of World Records, what would it be for?

  9. How would you describe me to your 12-year-old self?

  10. What is your favorite inside joke we have?

The Curio Cabinet: Random Questions to Spark Your Boyfriend’s Imagination

Time to mix it up! Let’s have some fun with totally random, off-the-wall questions to uncover your boyfriend’s quirky side. 

  1. If you could have any animal as a pet, what would it be?

  2. What’s your go-to karaoke song?

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

  4. What’s your favorite guilty pleasure movie or TV show?

  5. What’s the weirdest food you’ve ever tried?

  6. If you could instantly learn any language, which one would you choose?

  7. If you could invent a new national holiday, what would it be?

  8. What’s the best prank you’ve ever pulled?

  9. If you could only listen to one song for the rest of your life, what would it be?

  10. If you could only eat one meal for the rest of your life, what would it be?

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:

Make a Mystery Question Jar

Stuck on what to ask first? Try a "Mystery Question Jar." Write down your favorite deep questions to ask your boyfriend from the list on slips of paper, fold them up, and place them in a jar or bag. During a date night, take turns drawing a question and answering it. This adds an element of surprise and takes the stress out of choosing what to talk about. 

Try a Conversation Starter Game

There are so many questions to ask – this list is just a starting point! Thankfully, there are many board games and card decks designed specifically for couples to focus on relationship-building questions like these. Games like "We're Not Really Strangers,” "The And,” or “Actually Curious” give you a structured yet playful way to expand on these questions and keep learning more about one another. 

Explore the Waffle App Prompts

Waffle was designed to help you deepen your relationships through daily moments for reflection and connection. We have many more thoughtful prompts on the app to make asking and answering meaningful questions part of your daily routine without feeling forced. 

Like Waffle-journaler Justeen says, “My boyfriend and I are closer by using Waffle and it lets us get to know each other better due to the prompts that ask questions that we wouldn’t even think to ask each other.” 

Each day, the app offers a new prompt for you both to answer and share when it feels right. You can answer these on your own, or set a time each day to talk through them together (like over coffee in the morning, or settling into bed at night). Justeen and her boyfriend live far apart, so they complete the prompts when it works for them. “I get to know the inner workings of his brain due to the thought provoking questions as well as wake up to cute messages.”

Whether you’ve been married to your “boyfriend” for 20 years, are navigating a long-distance relationship, or simply want to become a better partner, Waffle keeps you close. 

Stay Curious, Compassionate, and Connected with Waffle  

Thanks to technology, we’re more connected than ever. Yet, so many people still feel disconnected, isolated, and alone despite our instant access to others through social media and messaging apps. 

The trouble is, these methods of staying in touch don’t always allow for the deep and meaningful conversations we really want to have with one another. But with Waffle, it’s different. 

Waffle gives you a safe space to clear your head, ask the deep questions, and be yourself through shared journaling. And with prompts like these, you can easily shift away from the mundane small talk to meaningful conversations that open the door to a stronger, happier relationship. 

So, which questions will unlock new levels of connection with your boyfriend? Download the Waffle app today and turn a new page in your relationship! 

How well do you really know your boyfriend?

The truth is, we’re all complex, layered people with deep lives and even deeper thoughts. You may never know your boyfriend like you know yourself, but you can get close. Asking deep questions to get to know someone is one of the best ways to see the world from their eyes and communicate with them better. 

So, what are some deep questions to ask your boyfriend?

There are thousands of questions to ask and countless conversations waiting ahead of you. But for now, let’s get inspired with these 100 deep questions and shared journal prompts

Why Ask Questions?

Before we dive into the questions, you might be wondering, why bother with these deep questions anyway? 

Deep conversations aren’t just for therapy sessions or serious talks. These questions can become your secret weapon for building a stronger, more intimate relationship. Here’s why they’re so important:

  • Feel More Connected When You’re Apart
    Work travel, deployment, and long-distance relationships can keep you and your boyfriend miles apart. Staying connected across the distance can be challenging, but deep questions like the prompts in the Waffle app help bridge the gap.


    “I use it [Waffle] nearly every day with my long distance boyfriend,” says our user Nova. “We like to answer the daily prompts so we can learn more about each other. I'd say it's made myself and my partner feel much closer to each other. The questions asked are genuine and interesting, and not necessarily something I'd think to ask him on my own. I'm always looking forward to seeing his answers and learning more about the way he thinks. He's said the same of my answers, too...It makes us feel so much more connected.”

  • Make Opening Up and Communicating Easier
    Let’s face it, not everyone is great at expressing their feelings. Deep questions provide a comfortable way to ease into those important conversations, making it easier to open up and communicate effectively.

    Jake and his girlfriend found that taking time to ask deep questions didn’t just strengthen their relationship – it saved it. “In some ways, Waffle played a big role in saving our relationship. My girlfriend and I had been friends for over a year before we started dating, so once we hit a pretty rough patch about a month in, I was scared that I'd not only lose my girlfriend, but my best friend also. The problems we were facing mostly had to do with a lack of communication, and I was ultimately drawn to Waffle because of its daily prompts – which I thought would help us get to know each other better by finding new things to talk about.”

  • It’s a Fun Way to Bond and Grow Closer
    Who says deep conversations have to be heavy? Asking these questions can be a fun and engaging way to bond, laugh, grow closer, and even discover new sides to each other. Our user James and his girlfriend used deep question prompts in Waffle as a way to capture memories: “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. This has helped us become closer and feel more cherished by the other.” 

The Art of Conversation: Tips for Asking Questions 

Getting to know anyone – including your boyfriend – is a bit like a treasure hunt. Perhaps you have an idea of what kind of treasure you’re looking for, or where you might start searching. But where ‘X’ marks the spot is just the surface. You have to dig deep to get to the real treasure, and you might be surprised by what you find! 

Just like a treasure hunt, searching for more meaning in your relationship may lead you down paths you never expected to find rewards you never imagined. Truly getting to know someone goes beyond scratching the surface—it requires digging deeper into their thoughts, memories, and opinions to explore who they really are. But deep conversations aren’t always easy. 

Here are some tips to help you become a master at asking deep questions:

  • Choose the Right Time
    Timing is everything. Select moments when both of you are relaxed and free from distractions. Ideal times might include a quiet evening at home, a leisurely weekend morning, or during a long walk. Avoid bringing up deep questions during stressful or busy times. The Waffle Journal app makes this part effortless. Simply send your question or prompt and your boyfriend can choose when they feel ready to respond.

  • Create a Safe Space
    Not everyone likes to wear their heart on their sleeve. Many of us need time or a certain environment to feel ready to share. You can help put them at ease by setting the stage for an open and compassionate conversation. Try a cozy, intimate setting, like a candlelit dinner or a quiet park, where you both can feel free to open up.

  • Start with Light Topics
    Want to ask some deep questions on your next date or through the Waffle Journal app? Take it slow. Rather than jump head first into the serious questions, ease in with a few lighter, fun topics first. This will build comfort and trust and may open some interesting doors for conversation.

  • Respect Boundaries and Comfort Levels
    If your boyfriend seems uncomfortable or hesitant to answer a question, that’s okay. It’s more important to respect his boundaries  than get an answer – after all, the whole point is to grow closer, not push someone away. Not every question needs to be answered immediately, and time to process and reflect can lead to even more meaningful conversations later on.

  • Share and Reflect Together
    Asking your boyfriend deep romantic questions should feel like a mutual exchange, rather than an interrogation. After he’s answered, reflect on what he shared and offer your own thoughts and feelings on the topic. 

Deep Questions To Ask Your Boyfriend  

Ready to dive in? Asking your boyfriend deep questions is one of the best ways to really get to know him. The questions in this set go far beyond everyday chit-chat and “how was your day?” We’re going to swing open the door to understanding his innermost thoughts, dreams, and values, all while making him feel heard and loved. 

Inner Child Playdate: Questions to Ask About Their Family & Past 

Ever wondered what your boyfriend was like as a kid? Would you have been fast friends on the playground? Reminiscing on childhood stories is not only a great way to understand what shaped your boyfriend, but invites his inner child out to play. Get ready to dive into tales of family traditions, childhood dreams, and those adorable little quirks that make him who he is today.

  1. What is your fondest childhood memory?

  2. What was your relationship like with your parents growing up?

  3. What’s your weirdest family tradition?

  4. What’s the most valuable lesson you learned from your childhood?

  5. Who were you closest to in your family and why?

  6. What were you exceptionally good at as a kid?

  7. What toy from your childhood would you love to play with again?

  8. What was your favorite family vacation?

  9. What’s a childhood fear that you’ve overcome?

  10. Which childhood friend would you love to reconnect with most?

Co-Create a Dream Future: Questions to Ask About Their Aspirations

We’ve talked about the past, now let’s dream about the future! These questions are your ticket to exploring your boyfriend's biggest goals and wildest ambitions. Whether he's dreaming of starting his own business, going on an adventure, or mastering a new skill, this is your chance to cheer him on and maybe even plan some dreams together. Let’s map out an exciting future…

  1. What is your biggest dream or goal in life?

  2. What would you like to be different about your life in one year? What about five years?

  3. What motivates you most to reach your goals?

  4. What’s a career milestone you’re most proud of?

  5. What personal skills or traits are you working on improving?

  6. If you could wake up tomorrow in a different place, where would you like to be?

  7. If you could own a business, what would it be?

  8. How would you spend 10 million dollars?

  9. What is something you’ve always wanted to try but haven’t yet?

  10. How do you envision our future together? Where do we live? What do we do for fun?

Take the High Road: Questions to Explore Their Values & Beliefs 

We all live according to a different set of values, morals, and ethics. What seems black and white to you may be gray matter for your boyfriend, or vice versa. Asking these deep questions about your values is one of the best ways to better understand how your boyfriend thinks about the world and may even help you both gain a wider perspective. 

  1. What three values do you think “good people” have in common?

  2. How do you define success?

  3. What moral dilemma are you stumped by?

  4. What causes or issues are you passionate about?

  5. Is it better to be honest or kind? 

  6. What do you believe is the key to a fulfilling life?

  7. How important is spirituality or religion to you?

  8. What’s a belief you hold that might be considered unconventional?

  9. What is something you do (or don’t do) that feels “off-brand” for you?

  10. What’s the biggest misconception people have about you/

Nurture Your Love: Deep Questions to Ask Your Boyfriend About Your Relationship

We’ve asked deep questions to get to know your boyfriend, so now let’s go deep into your relationship. Talking about your relationship is something many couples put off until frustration and irritation builds into an argument. Not you! Let’s dig into what's working, what could use a little TLC, and how you can grow stronger together. Get ready to chat about love languages, favorite memories, and ways to keep the romance alive. 

  1. What do you like most about our relationship?

  2. When do you feel most loved and appreciated by me?

  3. What’s your love language? 

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

  5. What’s your favorite memory of us?

  6. What do you remember most about our first date?

  7. What’s your favorite way to spend quality time together?

  8. How do you feel we can improve our communication?

  9. What’s a challenge we’ve faced together that made us stronger?

  10. How do you like to be supported during tough times?

Between the Sheets: Questions to Ask About Sex & Intimacy 

Intimacy (in whatever form that takes for you) is a necessary part of any healthy, fun, rewarding relationship. But, being open and vocal about what we want with sex and intimacy can be a touchy subject. These deep romantic questions can help set the mood for a deeper physical and emotional connection, whether you're looking to explore new fantasies or understand each other's boundaries better.

  1. What about me turns you on the most?

  2. What are your boundaries when it comes to physical intimacy?

  3. How can we improve our sexual connection?

  4. What’s something new you’d like to try together?

  5. What’s your favorite way to be touched? 

  6. What sexual frequency feels right for you?

  7. How do you feel about PDA?

  8. What’s your favorite memory of an intimate moment we’ve shared?

  9. How do you feel about incorporating toys or accessories into our sex life?

  10. What can I do to make you feel more comfortable during intimate moments?

Dive into the Deep End: Questions to Embrace Vulnerability 

Embracing vulnerability can feel scary at first, but actually helps you strengthen your bond and build a foundation of trust. Let's dive into the deep end and get real with each other.

  1. What’s your biggest fear in life?

  2. Is there anything about our relationship that scares or tests you?

  3. What’s a personal insecurity you struggle with?

  4. When is failure a good thing?

  5. What’s a difficult experience that has shaped who you are today?

  6. How often do you feel lonely? How do you handle feelings of loneliness?

  7. What’s something you’ve never told anyone before?

  8. How do you process and express emotions?

  9. What’s a regret you have, and what did you learn from it?

  10. What’s a dream or goal you’re afraid to pursue?

The Big Stuff: Important Questions to Ask Your Boyfriend 

Are you and your boyfriend on the same page about big issues and long-term plans? From commitment and kids to finances and family dynamics, these questions help you break the ice on some more challenging big-picture conversations to gauge your lifetime compatibility. 

  1. How do you define a successful relationship?

  2. Do you see yourself getting married (or a similar commitment) one day?

  3. What are your “deal-breakers” for a long-term committed relationship?

  4. Do you envision a life with children? If so, how would you want to raise them?

  5. How do you think we should manage finances in our relationship?

  6. How do you handle major life decisions?

  7. What are some relationship goals you have for us?

  8. If we had a major conflict, what would you do to show forgiveness? What would you expect me to do to show you forgiveness?

  9. Do you think any relationship could survive infidelity or cheating?

  10. What obstacles do you foresee us overcoming in our long-term relationship?

Light & Fun Questions to Ask Your Boyfriend 

Whew, that’s deep. Now, let’s shift the conversation to something a little lighter. Not all conversations need to be deep and serious to be meaningful. In fact, lighthearted questions can open up some really interesting aspects of your boyfriend and your relationship together. Plus, they add a touch of fun and whimsy while you bond. Ask these questions for a casual or quirky convo or to clear the air after a disagreement or deep dive. 

Your Life is a Movie: Questions to Put Your Boyfriend Center Stage 

Let’s bring some main character energy to this conversation. Whether you’re planning your imaginary superhero abilities or designing your dream house, these questions are all about having fun and seeing where your imagination takes you.

  1. If your life were a movie, what genre would it be?

  2. Who would play you in a movie about your life?

  3. If you could live in any fictional world, which one would you choose?

  4. What would the title of your autobiography be?

  5. If you could have any superpower, what would it be and why?

  6. You’re the main character of a movie, sitting in the back of a taxi and looking longingly out the window as you drive through the rain. Where are you going?

  7. If you could have dinner with any three people, dead or alive, who would they be?

  8. What’s a skill you wish you could master instantly?

  9. If you could time travel, where and when would you go?

  10. What’s a crazy invention idea you have?

Felt Cute: Flirty Questions to Ask Your Boyfriend

Let’s make your boyfriend blush. These questions are perfect for date nights or cozy moments, or whenever you want to remind yourselves why you’re so smitten with each other.

  1. What’s your favorite physical feature of mine?

  2. What do you think makes our relationship unique?

  3. What city best represents our relationship and why?

  4. What’s your favorite thing to do together?

  5. What’s a nickname you love being called by me?

  6. What’s the most romantic thing you’ve ever done? What’s the most romantic thing I’ve ever done for you?

  7. What’s a song that reminds you of us?

  8. If we made it into the Guiness Book of World Records, what would it be for?

  9. How would you describe me to your 12-year-old self?

  10. What is your favorite inside joke we have?

The Curio Cabinet: Random Questions to Spark Your Boyfriend’s Imagination

Time to mix it up! Let’s have some fun with totally random, off-the-wall questions to uncover your boyfriend’s quirky side. 

  1. If you could have any animal as a pet, what would it be?

  2. What’s your go-to karaoke song?

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

  4. What’s your favorite guilty pleasure movie or TV show?

  5. What’s the weirdest food you’ve ever tried?

  6. If you could instantly learn any language, which one would you choose?

  7. If you could invent a new national holiday, what would it be?

  8. What’s the best prank you’ve ever pulled?

  9. If you could only listen to one song for the rest of your life, what would it be?

  10. If you could only eat one meal for the rest of your life, what would it be?

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:

Make a Mystery Question Jar

Stuck on what to ask first? Try a "Mystery Question Jar." Write down your favorite deep questions to ask your boyfriend from the list on slips of paper, fold them up, and place them in a jar or bag. During a date night, take turns drawing a question and answering it. This adds an element of surprise and takes the stress out of choosing what to talk about. 

Try a Conversation Starter Game

There are so many questions to ask – this list is just a starting point! Thankfully, there are many board games and card decks designed specifically for couples to focus on relationship-building questions like these. Games like "We're Not Really Strangers,” "The And,” or “Actually Curious” give you a structured yet playful way to expand on these questions and keep learning more about one another. 

Explore the Waffle App Prompts

Waffle was designed to help you deepen your relationships through daily moments for reflection and connection. We have many more thoughtful prompts on the app to make asking and answering meaningful questions part of your daily routine without feeling forced. 

Like Waffle-journaler Justeen says, “My boyfriend and I are closer by using Waffle and it lets us get to know each other better due to the prompts that ask questions that we wouldn’t even think to ask each other.” 

Each day, the app offers a new prompt for you both to answer and share when it feels right. You can answer these on your own, or set a time each day to talk through them together (like over coffee in the morning, or settling into bed at night). Justeen and her boyfriend live far apart, so they complete the prompts when it works for them. “I get to know the inner workings of his brain due to the thought provoking questions as well as wake up to cute messages.”

Whether you’ve been married to your “boyfriend” for 20 years, are navigating a long-distance relationship, or simply want to become a better partner, Waffle keeps you close. 

Stay Curious, Compassionate, and Connected with Waffle  

Thanks to technology, we’re more connected than ever. Yet, so many people still feel disconnected, isolated, and alone despite our instant access to others through social media and messaging apps. 

The trouble is, these methods of staying in touch don’t always allow for the deep and meaningful conversations we really want to have with one another. But with Waffle, it’s different. 

Waffle gives you a safe space to clear your head, ask the deep questions, and be yourself through shared journaling. And with prompts like these, you can easily shift away from the mundane small talk to meaningful conversations that open the door to a stronger, happier relationship. 

So, which questions will unlock new levels of connection with your boyfriend? Download the Waffle app today and turn a new page in your relationship! 

How well do you really know your boyfriend?

The truth is, we’re all complex, layered people with deep lives and even deeper thoughts. You may never know your boyfriend like you know yourself, but you can get close. Asking deep questions to get to know someone is one of the best ways to see the world from their eyes and communicate with them better. 

So, what are some deep questions to ask your boyfriend?

There are thousands of questions to ask and countless conversations waiting ahead of you. But for now, let’s get inspired with these 100 deep questions and shared journal prompts

Why Ask Questions?

Before we dive into the questions, you might be wondering, why bother with these deep questions anyway? 

Deep conversations aren’t just for therapy sessions or serious talks. These questions can become your secret weapon for building a stronger, more intimate relationship. Here’s why they’re so important:

  • Feel More Connected When You’re Apart
    Work travel, deployment, and long-distance relationships can keep you and your boyfriend miles apart. Staying connected across the distance can be challenging, but deep questions like the prompts in the Waffle app help bridge the gap.


    “I use it [Waffle] nearly every day with my long distance boyfriend,” says our user Nova. “We like to answer the daily prompts so we can learn more about each other. I'd say it's made myself and my partner feel much closer to each other. The questions asked are genuine and interesting, and not necessarily something I'd think to ask him on my own. I'm always looking forward to seeing his answers and learning more about the way he thinks. He's said the same of my answers, too...It makes us feel so much more connected.”

  • Make Opening Up and Communicating Easier
    Let’s face it, not everyone is great at expressing their feelings. Deep questions provide a comfortable way to ease into those important conversations, making it easier to open up and communicate effectively.

    Jake and his girlfriend found that taking time to ask deep questions didn’t just strengthen their relationship – it saved it. “In some ways, Waffle played a big role in saving our relationship. My girlfriend and I had been friends for over a year before we started dating, so once we hit a pretty rough patch about a month in, I was scared that I'd not only lose my girlfriend, but my best friend also. The problems we were facing mostly had to do with a lack of communication, and I was ultimately drawn to Waffle because of its daily prompts – which I thought would help us get to know each other better by finding new things to talk about.”

  • It’s a Fun Way to Bond and Grow Closer
    Who says deep conversations have to be heavy? Asking these questions can be a fun and engaging way to bond, laugh, grow closer, and even discover new sides to each other. Our user James and his girlfriend used deep question prompts in Waffle as a way to capture memories: “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. This has helped us become closer and feel more cherished by the other.” 

The Art of Conversation: Tips for Asking Questions 

Getting to know anyone – including your boyfriend – is a bit like a treasure hunt. Perhaps you have an idea of what kind of treasure you’re looking for, or where you might start searching. But where ‘X’ marks the spot is just the surface. You have to dig deep to get to the real treasure, and you might be surprised by what you find! 

Just like a treasure hunt, searching for more meaning in your relationship may lead you down paths you never expected to find rewards you never imagined. Truly getting to know someone goes beyond scratching the surface—it requires digging deeper into their thoughts, memories, and opinions to explore who they really are. But deep conversations aren’t always easy. 

Here are some tips to help you become a master at asking deep questions:

  • Choose the Right Time
    Timing is everything. Select moments when both of you are relaxed and free from distractions. Ideal times might include a quiet evening at home, a leisurely weekend morning, or during a long walk. Avoid bringing up deep questions during stressful or busy times. The Waffle Journal app makes this part effortless. Simply send your question or prompt and your boyfriend can choose when they feel ready to respond.

  • Create a Safe Space
    Not everyone likes to wear their heart on their sleeve. Many of us need time or a certain environment to feel ready to share. You can help put them at ease by setting the stage for an open and compassionate conversation. Try a cozy, intimate setting, like a candlelit dinner or a quiet park, where you both can feel free to open up.

  • Start with Light Topics
    Want to ask some deep questions on your next date or through the Waffle Journal app? Take it slow. Rather than jump head first into the serious questions, ease in with a few lighter, fun topics first. This will build comfort and trust and may open some interesting doors for conversation.

  • Respect Boundaries and Comfort Levels
    If your boyfriend seems uncomfortable or hesitant to answer a question, that’s okay. It’s more important to respect his boundaries  than get an answer – after all, the whole point is to grow closer, not push someone away. Not every question needs to be answered immediately, and time to process and reflect can lead to even more meaningful conversations later on.

  • Share and Reflect Together
    Asking your boyfriend deep romantic questions should feel like a mutual exchange, rather than an interrogation. After he’s answered, reflect on what he shared and offer your own thoughts and feelings on the topic. 

Deep Questions To Ask Your Boyfriend  

Ready to dive in? Asking your boyfriend deep questions is one of the best ways to really get to know him. The questions in this set go far beyond everyday chit-chat and “how was your day?” We’re going to swing open the door to understanding his innermost thoughts, dreams, and values, all while making him feel heard and loved. 

Inner Child Playdate: Questions to Ask About Their Family & Past 

Ever wondered what your boyfriend was like as a kid? Would you have been fast friends on the playground? Reminiscing on childhood stories is not only a great way to understand what shaped your boyfriend, but invites his inner child out to play. Get ready to dive into tales of family traditions, childhood dreams, and those adorable little quirks that make him who he is today.

  1. What is your fondest childhood memory?

  2. What was your relationship like with your parents growing up?

  3. What’s your weirdest family tradition?

  4. What’s the most valuable lesson you learned from your childhood?

  5. Who were you closest to in your family and why?

  6. What were you exceptionally good at as a kid?

  7. What toy from your childhood would you love to play with again?

  8. What was your favorite family vacation?

  9. What’s a childhood fear that you’ve overcome?

  10. Which childhood friend would you love to reconnect with most?

Co-Create a Dream Future: Questions to Ask About Their Aspirations

We’ve talked about the past, now let’s dream about the future! These questions are your ticket to exploring your boyfriend's biggest goals and wildest ambitions. Whether he's dreaming of starting his own business, going on an adventure, or mastering a new skill, this is your chance to cheer him on and maybe even plan some dreams together. Let’s map out an exciting future…

  1. What is your biggest dream or goal in life?

  2. What would you like to be different about your life in one year? What about five years?

  3. What motivates you most to reach your goals?

  4. What’s a career milestone you’re most proud of?

  5. What personal skills or traits are you working on improving?

  6. If you could wake up tomorrow in a different place, where would you like to be?

  7. If you could own a business, what would it be?

  8. How would you spend 10 million dollars?

  9. What is something you’ve always wanted to try but haven’t yet?

  10. How do you envision our future together? Where do we live? What do we do for fun?

Take the High Road: Questions to Explore Their Values & Beliefs 

We all live according to a different set of values, morals, and ethics. What seems black and white to you may be gray matter for your boyfriend, or vice versa. Asking these deep questions about your values is one of the best ways to better understand how your boyfriend thinks about the world and may even help you both gain a wider perspective. 

  1. What three values do you think “good people” have in common?

  2. How do you define success?

  3. What moral dilemma are you stumped by?

  4. What causes or issues are you passionate about?

  5. Is it better to be honest or kind? 

  6. What do you believe is the key to a fulfilling life?

  7. How important is spirituality or religion to you?

  8. What’s a belief you hold that might be considered unconventional?

  9. What is something you do (or don’t do) that feels “off-brand” for you?

  10. What’s the biggest misconception people have about you/

Nurture Your Love: Deep Questions to Ask Your Boyfriend About Your Relationship

We’ve asked deep questions to get to know your boyfriend, so now let’s go deep into your relationship. Talking about your relationship is something many couples put off until frustration and irritation builds into an argument. Not you! Let’s dig into what's working, what could use a little TLC, and how you can grow stronger together. Get ready to chat about love languages, favorite memories, and ways to keep the romance alive. 

  1. What do you like most about our relationship?

  2. When do you feel most loved and appreciated by me?

  3. What’s your love language? 

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

  5. What’s your favorite memory of us?

  6. What do you remember most about our first date?

  7. What’s your favorite way to spend quality time together?

  8. How do you feel we can improve our communication?

  9. What’s a challenge we’ve faced together that made us stronger?

  10. How do you like to be supported during tough times?

Between the Sheets: Questions to Ask About Sex & Intimacy 

Intimacy (in whatever form that takes for you) is a necessary part of any healthy, fun, rewarding relationship. But, being open and vocal about what we want with sex and intimacy can be a touchy subject. These deep romantic questions can help set the mood for a deeper physical and emotional connection, whether you're looking to explore new fantasies or understand each other's boundaries better.

  1. What about me turns you on the most?

  2. What are your boundaries when it comes to physical intimacy?

  3. How can we improve our sexual connection?

  4. What’s something new you’d like to try together?

  5. What’s your favorite way to be touched? 

  6. What sexual frequency feels right for you?

  7. How do you feel about PDA?

  8. What’s your favorite memory of an intimate moment we’ve shared?

  9. How do you feel about incorporating toys or accessories into our sex life?

  10. What can I do to make you feel more comfortable during intimate moments?

Dive into the Deep End: Questions to Embrace Vulnerability 

Embracing vulnerability can feel scary at first, but actually helps you strengthen your bond and build a foundation of trust. Let's dive into the deep end and get real with each other.

  1. What’s your biggest fear in life?

  2. Is there anything about our relationship that scares or tests you?

  3. What’s a personal insecurity you struggle with?

  4. When is failure a good thing?

  5. What’s a difficult experience that has shaped who you are today?

  6. How often do you feel lonely? How do you handle feelings of loneliness?

  7. What’s something you’ve never told anyone before?

  8. How do you process and express emotions?

  9. What’s a regret you have, and what did you learn from it?

  10. What’s a dream or goal you’re afraid to pursue?

The Big Stuff: Important Questions to Ask Your Boyfriend 

Are you and your boyfriend on the same page about big issues and long-term plans? From commitment and kids to finances and family dynamics, these questions help you break the ice on some more challenging big-picture conversations to gauge your lifetime compatibility. 

  1. How do you define a successful relationship?

  2. Do you see yourself getting married (or a similar commitment) one day?

  3. What are your “deal-breakers” for a long-term committed relationship?

  4. Do you envision a life with children? If so, how would you want to raise them?

  5. How do you think we should manage finances in our relationship?

  6. How do you handle major life decisions?

  7. What are some relationship goals you have for us?

  8. If we had a major conflict, what would you do to show forgiveness? What would you expect me to do to show you forgiveness?

  9. Do you think any relationship could survive infidelity or cheating?

  10. What obstacles do you foresee us overcoming in our long-term relationship?

Light & Fun Questions to Ask Your Boyfriend 

Whew, that’s deep. Now, let’s shift the conversation to something a little lighter. Not all conversations need to be deep and serious to be meaningful. In fact, lighthearted questions can open up some really interesting aspects of your boyfriend and your relationship together. Plus, they add a touch of fun and whimsy while you bond. Ask these questions for a casual or quirky convo or to clear the air after a disagreement or deep dive. 

Your Life is a Movie: Questions to Put Your Boyfriend Center Stage 

Let’s bring some main character energy to this conversation. Whether you’re planning your imaginary superhero abilities or designing your dream house, these questions are all about having fun and seeing where your imagination takes you.

  1. If your life were a movie, what genre would it be?

  2. Who would play you in a movie about your life?

  3. If you could live in any fictional world, which one would you choose?

  4. What would the title of your autobiography be?

  5. If you could have any superpower, what would it be and why?

  6. You’re the main character of a movie, sitting in the back of a taxi and looking longingly out the window as you drive through the rain. Where are you going?

  7. If you could have dinner with any three people, dead or alive, who would they be?

  8. What’s a skill you wish you could master instantly?

  9. If you could time travel, where and when would you go?

  10. What’s a crazy invention idea you have?

Felt Cute: Flirty Questions to Ask Your Boyfriend

Let’s make your boyfriend blush. These questions are perfect for date nights or cozy moments, or whenever you want to remind yourselves why you’re so smitten with each other.

  1. What’s your favorite physical feature of mine?

  2. What do you think makes our relationship unique?

  3. What city best represents our relationship and why?

  4. What’s your favorite thing to do together?

  5. What’s a nickname you love being called by me?

  6. What’s the most romantic thing you’ve ever done? What’s the most romantic thing I’ve ever done for you?

  7. What’s a song that reminds you of us?

  8. If we made it into the Guiness Book of World Records, what would it be for?

  9. How would you describe me to your 12-year-old self?

  10. What is your favorite inside joke we have?

The Curio Cabinet: Random Questions to Spark Your Boyfriend’s Imagination

Time to mix it up! Let’s have some fun with totally random, off-the-wall questions to uncover your boyfriend’s quirky side. 

  1. If you could have any animal as a pet, what would it be?

  2. What’s your go-to karaoke song?

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

  4. What’s your favorite guilty pleasure movie or TV show?

  5. What’s the weirdest food you’ve ever tried?

  6. If you could instantly learn any language, which one would you choose?

  7. If you could invent a new national holiday, what would it be?

  8. What’s the best prank you’ve ever pulled?

  9. If you could only listen to one song for the rest of your life, what would it be?

  10. If you could only eat one meal for the rest of your life, what would it be?

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:

Make a Mystery Question Jar

Stuck on what to ask first? Try a "Mystery Question Jar." Write down your favorite deep questions to ask your boyfriend from the list on slips of paper, fold them up, and place them in a jar or bag. During a date night, take turns drawing a question and answering it. This adds an element of surprise and takes the stress out of choosing what to talk about. 

Try a Conversation Starter Game

There are so many questions to ask – this list is just a starting point! Thankfully, there are many board games and card decks designed specifically for couples to focus on relationship-building questions like these. Games like "We're Not Really Strangers,” "The And,” or “Actually Curious” give you a structured yet playful way to expand on these questions and keep learning more about one another. 

Explore the Waffle App Prompts

Waffle was designed to help you deepen your relationships through daily moments for reflection and connection. We have many more thoughtful prompts on the app to make asking and answering meaningful questions part of your daily routine without feeling forced. 

Like Waffle-journaler Justeen says, “My boyfriend and I are closer by using Waffle and it lets us get to know each other better due to the prompts that ask questions that we wouldn’t even think to ask each other.” 

Each day, the app offers a new prompt for you both to answer and share when it feels right. You can answer these on your own, or set a time each day to talk through them together (like over coffee in the morning, or settling into bed at night). Justeen and her boyfriend live far apart, so they complete the prompts when it works for them. “I get to know the inner workings of his brain due to the thought provoking questions as well as wake up to cute messages.”

Whether you’ve been married to your “boyfriend” for 20 years, are navigating a long-distance relationship, or simply want to become a better partner, Waffle keeps you close. 

Stay Curious, Compassionate, and Connected with Waffle  

Thanks to technology, we’re more connected than ever. Yet, so many people still feel disconnected, isolated, and alone despite our instant access to others through social media and messaging apps. 

The trouble is, these methods of staying in touch don’t always allow for the deep and meaningful conversations we really want to have with one another. But with Waffle, it’s different. 

Waffle gives you a safe space to clear your head, ask the deep questions, and be yourself through shared journaling. And with prompts like these, you can easily shift away from the mundane small talk to meaningful conversations that open the door to a stronger, happier relationship. 

So, which questions will unlock new levels of connection with your boyfriend? Download the Waffle app today and turn a new page in your relationship! 

Waffle: #1 Shared Journal App

Connect, bond, and share emotional support

4.8 • 4K Ratings

Download Today

Waffle: #1 Shared Journal App

Bond and share emotional support

4.8 • 4K Ratings

Download

Waffle: #1 Shared Journal App

Connect, bond, and share emotional support

4.8 • 4K Ratings

Download Today