97 Smart Questions to Ask a Guy

Whether you’re only just getting to know someone or wanting to deepen your long-term relationship with them, the right questions can bring you closer together. Different types of questions can spark interesting conversations, help break the ice, or just provide insight into who he is as a person. This is why we’ve come up with 95 smart questions to ask a guy.

Asking questions is essential for developing meaningful relationships. It can help to foster mutual understanding and trust. Through relevant questions, we get to know the thoughts, feelings, and perspectives of others. They enable you to open up a dialogue where both people can share their beliefs and experiences.

If you figure out the right questions to ask a guy, it also enables you to discover whether you want the same things out of life and if your values are compatible.

97 questions to ask a guy

So let’s get stuck in. Here are 97 questions to ask a guy in three categories: questions to understand him on a deeper level, questions about what you want in a relationship, and questions to determine whether your futures are aligned.

We also explain why each question is important. We’ve broken them down into different categories.

43 questions to ask a guy to understand him on a deeper level

Here are some questions to help you get to know your guy on a deeper level.

1. What makes you happy?

This question seems simple, but it can tell you a lot about your guy. It’s a way of taking a step back and focusing on the big picture. You can use this information to look out for ways to bring joy and happiness to his life. 

2. What are your biggest strengths and weaknesses?

This question can give you an insight into how your guy sees themselves. It’s a great way to understand how self-aware they are and what areas they need to work on. You might not agree, but it’s always interesting to know how someone views their own characteristics.

3. What makes you unique?

This question helps you to get a clear understanding of who your guy is as an individual. It allows them to open up and share what makes them stand out from the crowd. It can also help to reveal aspects of their personality that show their creativity and originality.

4. What are your biggest fears?

Fear is a natural part of life, and knowing your guy’s biggest fears can be helpful in understanding how their mind works. It can also help you to be more supportive when they are feeling anxious, and it enables you to be more aware of how they are impacted by different situations.

5. What is your personality type?

This can be an interesting question to ask. Personality types give you a framework to figure out how your guy processes information and why they behave in certain ways. It also gives you insight into why they react to certain situations in certain ways. Our favorite personality type framework is 16 personalities, but there are others you can use if you prefer, such as Enneagram or the Big Five.

6. Do you believe that different genders are better suited to certain roles?

This question can help you understand your partner’s beliefs about gender roles and if they subscribe to traditional or progressive views. Questions around gender roles can provoke conversations that can be eye-opening.

7. What is your attitude toward drugs?

This question can help you understand how your guy views drugs. This can be a dealbreaker in some circumstances. For some people, drugs are a way of life, and for others, they are a no-go area. It can also give you an indication of how he views his health.

8. What makes you feel vulnerable?

This is a great question to ask to gain an understanding of your partner’s emotional needs. It can help you be more supportive and create a safe space for him to open up and express himself. Essentially, if you know what makes him feel vulnerable, you can be more mindful about how you act when these situations arise.

9. How long have you known your closest friends?

This is a great question to get an understanding of how important relationships are to your partner. It can tell you how committed they are to the people in their lives and how loyal they are to the people that matter most. However, it’s not automatically a dealbreaker if they don’t have many long-term friendships. It could simply be that they met people they clicked with later in life.

10. Are you close with your family?

It’s important to understand how your guy interacts with their family, for example, how often they see each other and what kind of relationship they have. It can help you get an understanding of how they were raised and the values they were taught. You can also ask what your partner’s parent’s relationship was like and if it impacted their own views of relationships.

11. Would you like to be famous?

This question can give you an insight into whether or not your guy is motivated by fame and recognition. Some people prefer a quiet life, while others are drawn to the spotlight. There’s no right or wrong here. Either way, you should drill down to their core motivations. Asking this question can challenge them to think deeply about why they would or wouldn’t want to be famous.

12. What are your religious beliefs?

While this might not be an important factor for everyone, it’s a good idea to ask about your partner’s religious beliefs because they can play a significant role in their lives. This can help you understand if your beliefs are compatible and how you can support each other if they are different.

13. What were you like in school?

This question can help you gain a better understanding of how your partner was in the past. It’s interesting to know how they were as a student, what things they were passionate about, and how their school experience affected them. It can give you an insight into the kind of person they are today.

14. Are you a spiritual person?

This is a great question to ask to get an understanding of how your guy approaches life. It can give you insight into their beliefs and how they view the world. You can go on to ask how they define spirituality and what it means to them, as this differs from person to person.

15. What kind of hobbies do you enjoy?

This question can give you insight into your partner’s passions and interests. It reveals how they like to spend their leisure time, which can tell you a lot about someone. Knowing what type of hobbies they enjoy can also help you to find activities that you can do together.

16. Are you a night owl or an early bird?

This is another great question to ask to gain an understanding of how your partner operates. Knowing their sleeping patterns and preferences can help you work out how to create lifestyles that complement each other. It can also help with scheduling and planning activities together.

17. What traditions do you uphold?

It’s helpful to know what traditions he takes seriously. It can be anything from celebrating certain holidays like Valentine’s Day to honoring birthdays. This can help you appreciate the things that are important to him and be more respectful of how he chooses to live his life.

18. What is your approach to drinking alcohol?

This question can help you to understand your partner’s relationship with alcohol and how they handle it. Some people have very strict rules when it comes to drinking, while others are more relaxed. You don’t need to have the same drinking habits as long as you respect each other’s decisions.

19. How do you relax?

Knowing how your partner destresses and relaxes can help you to support them in times of need. It can also give you ideas for activities that the two of you can do together to have fun. There will be times when you both are feeling overwhelmed, and it’s helpful to be aware of how your guy destresses in advance.

20. Where is your favorite place to visit?

Knowing where your partner likes to go can indicate whether you would enjoy going on trips together. For example, are cities or beaches more their thing? It can also help you to understand which places they feel most at home in and what kind of activities they like to do when they are in that location.

21. Have you ever done anything illegal?

This is an important question to ask if you’re looking to gain a deeper understanding of your partner’s character. It can give you an idea of his morality and his approach to following (or breaking!) the rules.

22. Do you believe in the paranormal and supernatural?

Believing in the paranormal and supernatural, such as ghosts and spirits, can be a defining part of our beliefs and values. Asking this question can give you an insight into how your guy views the world. It can also help to open up conversations about other unconventional beliefs that you both have.

23. Do you have a sweet tooth?

Knowing if your guy has a sweet tooth can help you when it comes to buying surprise treats or gifts for them. It can also be a way of identifying date ideas that you could do together, like visiting a bakery or going for ice cream.

24. What is the biggest risk you have ever taken?

Asking about the biggest risk your guy has ever taken can help you gain an understanding of the type of person they are. Risk appetite, and risk tolerance, affect how we approach life in general. Knowing this about your partner can help you to understand their thought process when it comes to making decisions.

25. What are you most passionate about in life?

This is a great question to ask because it can give you an insight into what makes your guy tick. Knowing what motivates and drives them can be helpful in understanding their overall character and what makes them unique. It can also help you to appreciate the things that matter most to them.

26. What has been the most challenging period of your life?

Sharing difficult experiences is an important part of any relationship. Knowing how your guy responds to and handles hardship can help you gain a better understanding of their coping mechanisms and resilience. It can also give you an opportunity to provide support.

27. Are you in touch with your emotions?

This question is rarely asked but it’s important to know your guy’s answer. Knowing how in tune they are with their emotions can help you understand how they handle difficult situations. Some people are more adept at understanding and processing their feelings than others and it’s beneficial to know where your partner sits on that spectrum.

28. Do you have any unconventional views?

Asking whether your partner has any unconventional views can be a great way to understand their perspective on certain topics that might not have come up naturally in conversation yet. It can give you insight into how their views differ from the mainstream. It can also enable you to appreciate their individual worldviews or discover any red flags.

29. What does being a ‘good person’ mean to you?

This question can help you to get an understanding of how your partner defines morality. It can also give you an idea of their values and principles. It’s important to know how your guy judges themselves and others in order to gain a better appreciation for their character.

30. Which movie character do you most relate to?

This is a fun question to ask that can also give you an idea of how your partner views themselves. Knowing which characters they identify with can help you to better understand their perspective of their own characteristics and their level of self-awareness.

31. Do you have any health issues that you are comfortable sharing?

Asking this question can be awkward. But it enables you to understand your partner’s health and well-being. However, it’s worth bearing in mind that some people are private about their health. So they might not want to share this information for a while. Whether they are willing to share depends on the individual, your connection, how long you have been together, and the trust you have built between you. 

32. Do prefer to be spontaneous or plan in advance?

This is a great way to get an understanding of how your guy likes to live their life on a daily basis. Knowing if they prefer to plan every detail in advance or if they prefer to be spontaneous can help you to know how to approach activities them.

33. What are you most proud of in life?

This is a great question to ask as it can give you an insight into what makes your partner feel fulfilled. Knowing what they take pride in can help you to better understand their values and how they measure success. It can also be an opportunity to celebrate their biggest achievement.

34. Which famous person do you admire most?

Asking which famous person your guy admires most is a fun way to get to know them better and find out who they look up to. It can be a great conversation starter, and although it might seem like a simple question, it can tell you a lot about what traits they value in others and what they aspire to.

35. Do you believe in a higher power?

This is an important question to ask if you’re looking to understand your partner’s spiritual beliefs. Even if someone isn’t religious, they may believe in a certain kind of energy or higher power that guides their actions.

36. Why did you choose your current career?

Knowing the reason behind why your guy chose their current profession can be helpful in understanding their motivations and goals. It can give you an insight into what they prioritize, and it can also be a great way to appreciate the hard work they have put into achieving their goals.

37. Is there anything you regret?

This is another difficult but important question to ask your partner. It can help you understand their feelings about the past, and it can be a way to show that you are understanding and supportive of whatever they may have gone through.

38. What kind of music do you like?

You might know the answer to this already, depending on how long you have been together, but it doesn’t hurt to ask explicitly. Knowing what music your partner enjoys can give you a more rounded view of them as a person. It can also spark some ideas for birthday and Christmas gifts!

39. What are your thoughts on politics?

Politics can be a touchy subject, but it’s important to know your partner’s opinions and beliefs. This can give you a better insight into what values they hold, how they view the world, and how their views might differ from yours.

40. What do you want to be remembered for?

This can be one of the most profound questions you can ask someone. Knowing what your partner wants to leave behind and how they want the world to remember them can give you a better understanding of their deepest, most closely-held values.

41. Have you ever been to therapy?

Therapy can be a great way to process personal issues, and there are many positive traits associated with men who have been to therapy. This question shows you whether they have sought professional help to resolve issues in the past. It’s a great sign if your partner is willing to seek help when needed. However, some men prefer to work through issues alone, and it’s important to respect that as well.

42. When was the last time you felt frightened?

This can be a difficult question to answer, and it’s possible that your partner may not feel comfortable talking about it. However, insight into the things in life that scare someone can give you a better understanding of how they handle fear and difficult emotions. It can also help you both connect on a deeper level.

43. What am I yet to understand about you?

This is an insightful question to ask to get to know your partner on a deeper level and to strengthen your connection. It can help you discover aspects of your partner’s personality that may not have surfaced yet. In fact, it can even build attraction because it can highlight the different dimensions of your partner’s personality.

15 questions about whether your futures are aligned

Here are some questions to ask to determine whether your futures are compatible.

1. How do you see your future?

This question might seem a little vague, but it’s a great one to ask your partner in a new relationship. The areas that they focus on will indicate which areas of their life are a priority for them. It will also help you to work out if you share a similar outlook and whether spending your future together could be feasible.

2. Do you want children?

It’s also important to ask about their thoughts on family life. You should delve into the details of whether they want children and if so, how many. Family-related decisions are often a dealbreaker, so discussing your goals in this area can help you both decide if your futures are aligned. 

3. What does your ideal future look like?

This question can help you to understand your guy’s hopes and dreams for the future. It can also give you an insight into what they value and, ultimately, what matters to them. Last but not least, it can help you to assess if you both want the same things.

4. Is there anything you would change about your life?

Understanding whether someone wants to make changes in their life gives you insight into improvements that they are striving for. It can be interesting to see how their current life compares to their ideal life. And whether they are actively making improvements in the areas you discuss.

5. How important is your career to you?

This is a great question to gauge how important career advancement and achieving success is for your guy. It might also help you to understand their long-term plans and how they will prioritize different aspects of their life going forward.

6. What is your dream job?

This question is a good way to figure out what interests and motivates your partner. It can also give you clues about how ambitious they are in their career, and you’ll discover what type of job they would love to do if all obstacles were removed.

7. Where do you want to live?

Asking this question can help you gain insight into what kind of lifestyle your guy wants to live and what kind of locations they find attractive. It can also give you a better understanding of how important certain parts of the country or the world are to them.

8. What are the three five things on your bucket list?

This is a great way to get to know someone in more depth and understand some of the big things they want to achieve in life. It can also give you an idea of how adventurous they are and what type of experiences they want to have in life.

9. Are there any investments you want to make in the future?

This question can help you understand what types of investments your partner is interested in. It can also give you an insight into how they view money and their attitude toward risk in terms of financial matters. Being on the same page in terms of finances can help to minimize tension.

10. What is the next goal you are working towards?

This is one of the questions you should ask a guy to help you understand what motivates them and what goals they have set for themselves. It can give you an insight into what they are working on in the foreseeable future. This can help you work out how to support them and whether it will impact your relationship.

11. What do you want to achieve in the next five years?

Asking this question can give you insight into your partner’s medium-term aspirations and plans for the future. It can also help you to understand how they view success and how relationships fit into their grand plan. In addition, it can encourage you both to come up with a roadmap for achieving your shared goals.

12. Do you have any personal growth goals that you are working towards?

This is a great question to understand someone’s views on personal development. It can give you an insight into how they view their potential and what they believe is important to focus on in order to become the best version of themselves. It can also give you an idea of how they prioritize self-improvement.

13. What are your top three values?

Asking about someone’s top values can be very revealing because it gives you an insight into what your guy believes in and the principles they live by. Understanding their values can help you to get an idea of what they prioritize and what is important to them. And it helps you to see if your values are aligned.

14. What is your risk appetite in life?

This question can help you understand how your partner views risk and how they make decisions. It can also give you a better understanding of how they evaluate potential opportunities. In the long run, it can cause strain if two people have very different opinions on risk.

15. How do you manage your finances?

Money is often a source of stress in relationships. Asking this question can give you an opportunity to discuss openly how each of you handles finances and avoids future conflicts. It’s also useful to know if your partner is open to discussing their financial decisions or prefers to keep them private.

39 questions to understand what he wants from a relationship

Here are some questions to help you work out what he wants from a relationship.

1. What are your dealbreakers in a relationship?

This is a great question to ask early on. It helps you to understand what’s important for your guy when it comes to relationships and where they draw the line. In addition, it ensures that you are both compatible in terms of dealbreakers, which can help you to avoid difficulties further down the line.

2. What does being in a relationship mean to you?

It’s important to understand what being in a relationship actually means to your partner. This question can give you an insight into their values and how they define intimacy and commitment. You should include conversations around communication and mutual support, too. 

3. How do you show and receive love?

Everyone shows and receives love in different ways. Asking your partner this question can help you get a better understanding of how they express their love and what makes them feel loved. Many misunderstandings between couples arise from failing to recognize each other’s love language. So this is an important question to ask. 

4. How do you like to resolve conflict?

Conflict is inevitable in relationships, but how it’s handled is what matters most. Asking your partner about their preferred conflict resolution style can help you work out the best ways to handle disagreements. It will also help you both create strategies to deal with conflict.

5. What is most important to you in a relationship?

This is one of our top questions to ask a guy because it gives you an understanding of what your guy values in relationships. It can also give you both clarity about where you stand and what you can expect from each other.  Knowing what is most important to your guy can help you be mindful of their needs in the relationship and vice versa.

6. What are your biggest strengths and weaknesses in relationships?

Most of these smart questions to ask a guy are about getting to know him on a deeper level, and this is no exception. Not only can this question uncover his personality, but it can also help you understand how your relationship dynamic could play out in the future. It can encourage you both to be mindful of each other’s relationship blind spots.

7. What is the longest relationship you have had?

Asking this question can give you insight into your partner’s relationship history and how they deal with commitment. It also lets you know how much experience they have in relationships. You might also want to ask why your partner’s previous relationships ended and what they learned from them.

8. What makes you feel connected?

Knowing what makes your partner feel connected can help ensure that they are getting the emotional connection they need. This could be anything from spending quality time together to communicating regularly. Whatever it is, you should both know what makes each other feel connected.

9. What are your family and friend relationships like?

Taking the time to hear what your partner’s relationships with their family and friends are like can help you to better understand how they interact with their loved ones. It can also give you insight into how they view relationships and what kind of support system they have in place. 

10. How much alone time do you need?

This question can show you what kind of balance your partner needs in the relationship. Knowing how much alone time they need and respecting that is key to a healthy relationship. It also indicates the level of independence in your partner’s life and how much space they are comfortable with.

11. What qualities are most important to you in a partner?

Asking this question can help you gain clarity into what your guy is looking for in a partner. It can tell you a lot about what’s important to them in a relationship and if you are compatible. In addition, it can give you an opportunity to talk about any qualities that you both need in order to have a healthy and fulfilling relationship.

12. What do you expect from our relationship?

Knowing what your partner expects from your relationship can help you ensure that you are both on the same page. This is a good question to ask early on. It will give you an understanding of their intentions and can help you decide if the relationship is worth investing in.

13. What would your ideal relationship look like?

This question can give you insight into what success looks like to your guy when it comes to relationships. It can also motivate you both to get creative and come up with new ways to make your relationship stronger.

14. What do you need from me?

Asking this question can remind your partner that you are there for them. It can also help you understand what they need in order to feel secure and fulfilled in the relationship. This can help ensure that you are both getting the emotional support and connection you need.

15. Do you have any sexual kinks?

This can be a difficult question to ask, but it should be addressed. Understanding your partner’s kinks can help you navigate sexual activities in a way that is beneficial for both of you. Additionally, sexual kinks can be a dealbreaker for some people. So, even though it can be an awkward topic to discuss, it’s better to have this conversation sooner rather than later.

16. Are you dealing with any issues that might impact our relationship?

This question is rarely asked because it can be easy to assume that someone would have already brought up relevant issues. But at the beginning of a relationship, your guy might not know how to bring up personal challenges. So it gives them an opportunity to share private matters if they wish. Asking this question can help you learn more about their current situation and whether it could impact your relationship. This is a good time to discuss your partner’s mental health, too. 

17. Is a partner’s drinking habits important to you?

This is one of the questions to ask a guy that is sometimes overlooked. But it gives you the chance to discuss how alcohol consumption may affect the relationship. It can also help you both learn more about how each other views other people’s alcohol consumption.

18. What three things do you find most attractive about me?

This is a great question to ask in order to gain clarity about how your partner views you and your characteristics. It can also be an opportunity to express your appreciation for one another and increase the level of intimacy in your relationship.

19. Are you a flirt?

Well, you might know the answer to this one already! But asking this question can help you understand whether your guy views himself as a flirty person. It can also be a good way to gauge how your guy interacts with other people, which can be important for a healthy and trusting relationship.

20. Are there any topics that are off-limits?

This question can give you both an opportunity to discuss whether there are any topics of conversation that should be avoided. Knowing this can help you both feel comfortable discussing anything without fear of offending your partner or making them uncomfortable.

21. Is physical affection important to you?

Knowing whether your guy appreciates physical affection can give you the tools to build a stronger connection. It can help to ensure that both of you are getting the affection that you need in order to feel connected and secure in your relationship.

22. Does your family have any expectations of our relationship?

This question can help you understand how your partner’s family may view the relationship. Knowing this can help prevent any issues that might arise between you and your partner’s family. It can also help you both come up with strategies for how to handle any expectations that might be placed on the relationship.

23. Do you have any boundaries you want me to know about?

This is an important question to ask in order to ensure that your partner feels respected and safe within the relationship. Knowing each other’s boundaries can help you both build trust, which is the foundation of any healthy, fulfilling connection.

24. What is your biggest turn-on?

This is a great question to ask if you want to get more in-depth about your partner’s sexual desires. Knowing what your guy finds attractive can help you both feel more connected and intimate in the bedroom.

25. Are you monogamous?

If your relationship is going to move forward, understanding whether or not you and your partner are on the same page in terms of monogamy is important. Having an honest and open conversation about this can help ensure that both of you are aligned with what you want in terms of monogamy or non-monogamy.

26. Has anyone ever broken your heart?

Asking this question can give you a chance to learn more about your partner’s past relationships. Heartbreak can shape people in different ways, and it’s something that everyone remembers. It can give you insight into formative moments in your guy’s life that may have impacted them.

27. Are you friends with your exes?

There’s no right or wrong when it comes to being friends with exes. But knowing the answer to this question gives an indication of your partner’s level of closeness with previous partners. You should delve deeper into this one because the reasons for their answer can be a source of interesting and fruitful conversation.

28. What kind of conversations bring us closer?

This is an unusual but interesting question, and your guy might not have an answer. But any kind of discussion about this topic can help you both be more cognizant of the types of conversations that draw you closer together.

29. Do you want to get married?

Discussing marriage is something that should be done when both partners are comfortable (you might want to skip this question on the first date!). Bringing up this topic can give each of you an opportunity to discuss your individual feelings about marriage and what it means for both of you. It can also help you understand each other’s perspectives in terms of commitment and long-term plans.

30. Have you ever been in love?

This is another of our questions to ask a guy who can help you understand your partner’s past relationships and experiences. Love is arguably the most powerful emotion in the world. So, sharing your past experiences with love is often a sign of vulnerability and trust.

31. Do you believe in ‘the one’?

Asking whether your guy believes in ‘the one’ can help you understand whether they think there is a single perfect person out there for everyone. Or if they think that there are many potential partners who could be the ‘one’ depending on the circumstances. There’s no right or wrong, but it’s a good question to ask.

32. Have you ever broken anyone’s heart?

This question can be a way to find out more about how your partner has handled previous relationships. Knowing this can help you both understand how each other’s past experiences have shaped the way you approach relationships today.

33. What have you found challenging in previous relationships?

This question can give you an opportunity to discuss any issues that have been present in your partner’s past relationships. Knowing this can help you come up with strategies to avoid any potential issues in the future. It can also give you a chance to talk about how each of you has grown from experiences you’ve had in the past.

34. What is your preferred method of communication in a relationship?

Knowing your partner’s communication preferences can help you ensure that you regularly converse. Having an honest discussion about communication preferences can help you avoid any misunderstandings or disappointments while also allowing both of you to get your needs met.

35. Do you think that a couple can recover from cheating?

Cheating is a divisive topic. For some, it’s an instant dealbreaker. For others, there can be an opportunity to move forward after cheating. Asking this question will help you understand your partner’s stance and it can also give you both a chance to discuss what it means to be faithful.

36. What is the biggest risk you have ever taken when it comes to love?

This question can give you an insight into how your guy looks at relationships and how they deal with emotional risk. People often look at emotional risk through a different lens than physical or financial risk. Knowing their appetite for emotional risk can help you appreciate how bold they are when it comes to love.

37. Are you open to couples therapy?

Therapy can be a helpful way to ensure that your relationship stays healthy, even when things get tough. Asking your partner if they’re open to couples therapy can help to determine if it’s something they would be open to in the future if you hit a challenging patch in your relationship.

38. Are you comfortable having difficult conversations?

It’s not uncommon for people to shy away from difficult conversations in relationships. And it’s important to be aware of how open your guy is to have these kinds of discussions. Knowing this can help you both better manage any disagreements or conflicts that may arise.

39. Do you have any questions for me?

If you’ve got to this point, you’ll have asked a lot of questions! So now it’s time to turn the tables and ask your guy if there’s anything he wants to discuss. You’ll probably have discussed a whole range of topics by now, but it’s always good to check to see if there are any last questions.

Final thoughts on smart questions to ask a guy

The questions in this list are meant to be a two-way discussion. They are meant to open the door of communication between you and your partner. Asking open-ended questions can help you both learn more about each other and identify any potential areas of conflict.

Communication and mutual understanding are key to any successful relationship, so don’t be afraid to ask these questions and have honest, meaningful conversations. Knowing the answers to these questions will help you build a strong foundation for your relationship. Good luck!