These 20 questions to ask your boyfriend make getting to know him much easier!

Read more blogs about getting to know someone written by true relationship experts, such as myself at You can also follow this link for more ideas on what to ask!

I've written handfuls of blogs on dating advice which have garnered over a million readers, and here I'll go through the best questions to ask your boyfriend that make building a strong relationship more natural. I'll even throw in trick questions to ask your boyfriend to help spice things up!

Let's start.


Ultimate List of 20 Questions to Ask Your Boyfriend

Guys love it when a women ask questions about them that show she is interested and invested in the relationship. You can find a whole list of questions on this site. Many questions can be asked of a guy, but finding the right ones based on your relationship is also important to keep in mind.

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5 Best Things To Ask Your Guy To Know More About What He Wants In Life

Guys like it when they can get to know a woman through her questions. They feel special and appreciated for being approachable while working toward being more comfortable with you. In the long run, building a foundation of comfort makes it easier for you to discuss serious plans and emotions.

When you get to know your boyfriend, you want to make him feel comfortable around you, and you should ask him some questions to help him open up and talk about himself.

1. Do you want to have children?

Asking a guy whether or not he sees himself having children in the future is a good way to gauge his long-term goals and outlook. Depending on how old you two are, asking this question can give you an idea of how far he thinks ahead. Following up this question with how many children and when further gives you an idea of how your personalities and characters align.

2. Do you think money can buy happiness?

While money is not the only thing that keeps relationships from breaking, it can be a factor down the line when financial obligations start kicking in. Part of being in a relationship means knowing how to handle money together. Asking your boyfriend if he thinks money can buy happiness shines a light on how high the leader of priorities is.

In some cases, it can be read flag if it feels like money can solve every problem that comes his way.

3. What one thing do you want to accomplish in your life?

Everyone has that one thing they want to accomplish in their life. Some guys may not know right off the bat, but getting to know him, even with a general answer, can lead to more concrete ideas. He may even ask you for your ideas and inputs to better gauge where his ideal life goal fits.

Also, knowing what a guy wants to accomplish shows what is is passionate about. Sometimes, guys may even have a full plan to achieve that goal. This shows an excellent character with perseverance.

4. What is your love language?

Trying to guess someone's love language through trial and error is not an easy thing to do. Instead of assuming, it is healthier to ask them directly. Doing so goes a long way in making sure both of you feel secure and confident around each other. Adding to the benefit of asking your boyfriend this personal question, he may also show interest in learning your love language; he will also take care of you when you need it.

5. Do you hold grudges?

Holding a grudge is a bad habit that leads to unresolved issues and anger. Over time, it can fester and explode in the most unlikely times. Asking your boyfriend if he holds any grudges allows you two to work together in potentially resolving it before it gets out of hand.

Holding a grudge does not make a person automatically bad, but seeing how he handles it (or not) opens up conversations between the two of you on how to move forward with potential issues and misunderstandings in the future.

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5 Personal Question Ideas To Ask Him About His Past

Part of what makes someone unique and special is the events they went through in their past. It is by no means a pure definition of who they are, but having an idea of what life was like before you two started your relationship makes for an interesting conversation. It's also a wonderful way to get to know deeper characteristics and emotions he shows.

These personal questions to ask a guy also show that you are invested in getting to know who he is, which can make him feel more accepted and cared for.

6. Have you ever cheated on anyone? Have you ever been cheated on?

Personally, I don't believe in the phrase "once a cheater, always a cheater." People can change if they find a good reason to. Some guys may be embarrassed or ashamed at being asked this question if they have, but truthfully answering your question shows that he has full trust in you.

It's not easy to admit faults and being able to openly talk about them with each other shows a higher level of trust and communication that definitely benefits your relationship in the long run.

7. Why did you end up your previous relationship?

Accepting someone as your boyfriend means accepting that they had meaningful relationships before you. With that, there come lessons learned, but they can also shape his ideals and expectations in your relationship.

Having an idea of those expectations will help you communicate and resolve challenges more effectively. Also, it provides a deeper level of understanding for both of you.

8. What was the most difficult time in your life?

Everyone has some part of life that they consider the most difficult. Aside from those specific moments of difficulty, how someone gets past it shows their strength and ability to grow and move out of their comfort zone. Asking your boyfriend this personal question shows you are open to understanding him and are there for him come what may.

9. Do you keep mementos from past relationships?

Keeping mementos from past relationships can be a sign of sentimentality. In most cases, it does not mean they have any lingering feelings connected to those items. For example, they can have photos of people that were important to them but are no longer close friends. That doesn't mean they are in love with those people.

10. What is the biggest risk you've ever taken?

Taking risks in life is what moves someone to achieve greater things. Talking to your partner about the risks he has taken opens up discussions about the journey he has gone through to get to where he is. It's a great way to start deeper connections through shared experiences.

5 Fun Things To Ask Him When You're Bored Together

Even the most fun and outgoing couples will eventually become bored, but what better way to fill that time than with questions that make both of you laugh, such as those listed here on Mantelligence.

Even the simplest and most random fun questions can streamline meaningful conversations that let you two get to know each other more.

11. What word do you hate?

Some words sound so strange they can bug people. These words can be common everyday words or hard-to-pronounce ones that sound weird. Asking your boyfriend about the word or words that he hates is a fun question to start a lighthearted conversation.

You may find it odd that that specific word bothers him, but finding out what that word is will give both of you a good laugh.

12. What is the weirdest thing you've ever bought?

Spending sprees pop up from time to time when you have to buy something, no matter how useless or weird. Even your boyfriend is bound to have one or two strange purchases that make no sense. Even your boyfriend has likely fallen into the trap of buying the craziest thing on a spending spree high.

It's a simple question that leaves room for discussion. Perfect for boring days and keeps the conversation flowing.

13. What is your favorite part about being an adult?

Most people would ask what the hardest part of being an adult is. Taking a positive spin and asking what the most fun part is ideal for small talk that leads to fun conversations. With this question, you two can even compare interests and experiences that help with the bonding process.

14. What would you do if you could be a woman for a day?

Asking your boyfriend what he would do if he could be a woman for a day is interesting and can streamline into a flirty question. While it may seem embarrassing to ask, it's a great way to get to know the more fun side of your boyfriend. This question can be an icebreaker to get out of a boring weekday rut.

Who knows, you may uncover what his favorite designer dresses are or how willing he is to wear heels and a skirt!

15. What were you like in high school?

Finding out what your boyfriend was like in high school is a fun way to see just how far he has come. High school is usually when people start to discover who they want to be in life and learn who they are as individuals. Finding out how similar or different your boyfriend is from high school isn't just a fun conversation, but it also opens up about the steps he has taken to get to where he is today.

5 Questions About Relationship To Get Answers From Your Man

Asking your boyfriend questions about your relationship shows him you are willing to build emotional intimacy. Visit this article to get some ideas. Romantic questions are also w wonderful way for the two of you to express what you expect from each other emotionally and physically.

Moreover, asking your boyfriend questions about relationship offers up a chance for you to tell him your thoughts as well.

16. What is more important in a relationship: an emotional connection or a physical connection?

Emotional and physical connections are both important aspects of a relationship. However, its level of importance varies from person to person. Knowing what your boyfriend places more value on can help you learn how to communicate with him more effectively.

Don't feel disheartened with his answer is not the same as yours. The great thing about these two aspects is that there needs to be a perfect balance for a healthy relationship to form.

17. What is your ideal date?

Date nights and ideas are so much easier when you have a starting point to work with. Directly asking him what he considered his ideal date goes a long way in helping you plan a special date night for him down the line. You can incorporate his answers into your plans while also adding extra surprises to make the night as special as possible for him.

18. Do you believe in love at first sight?

Love at first sight is a wonderful idea that one can only hope to experience. While not all guys will believe in this, finding out if your boyfriend does can make for a super sweet topic of conversation. You may uncover an interesting story about your relationship with him!

19. What is your favorite thing about our relationship?

Relationships are full of ups and downs, but that does not stop anyone from having their favorite part. Your boyfriend is likely to have a few things about your relationship that he treasures the most. Keeping in mind his answer also gives you the chance to make him feel more loved by encouraging him to open up about his thoughts and feelings about where your relationship stands.

20. How can we support each other more?

Support is a HUGE part of any relationship. Ideally, you will always be balanced and coordinated, especially when making life decisions or taking on new challenges together.

Having a serious conversation about how the two of you can support each other more opens up the chance to learn how to better understand needs and what actions or words can support that.

Downloadable and Printable List of 20 Questions to Ask Your Boyfriend

Here is a downloadable and printable jpg/pdf list of 20 questions to ask your boyfriend (right-clicked the image and select Save Image As...):

Benefits of Asking Your Man Some Questions Occasionally

Asking your man the right questions at the right time builds interpersonal closeness so that you can feel secure around each other. In addition, this can lead to a deeper sense of intimacy between the two of you. Having that deeper connection and intimacy with each other contribute to a healthy, long-lasting relationship where your boyfriend feels safe in expressing himself.

Aside from that, asking him questions shows that you are interested in learning more about his wants and needs, which can lead him to appreciate your efforts and willingness to make the relationship as balanced as possible.

Tips On How To Make Your Man Engage in Your Conversation

Conversations between you and your boyfriend should be more than just meaningless words that go in one ear and out the other. Your conversations should engage both of you by keeping topics fun, interesting, and personal. While this may not come easily for those just starting their relationship, it is possible to get engaging conversations going.

Tip #1: Know When To Ask Certain Questions

The key to asking your boyfriend questions for engaging conversations is when to ask the right questions. This means that reading the mood and tone of the conversation is highly important.

You don't want to ask goofy out-the-box questions when your conversation is more serious and emotional. Rather, ask questions about what he is talking about. He will love it more if you seem focused on what he tells you, which adds respect and trust.

Tip #2: Don't Force Topics He Is Not Comfortable With

Certain questions are listed above that not all men will be comfortable answering or talking about. If you start to sense that he feels uncomfortable about answering, it is best to let it drop and move on to another topic. Remember, just because it is something you want to talk about with him doesn't mean he is ready to talk about it.

If it is an important question that affects your relationship, try asking him again another time when he seems more open and willing to discuss uncomfortable topics with you. Backing off at some points lets him know you respect his boundaries and are ready to wait for him to feel more at ease before discussing difficult topics.

Tip #3: Spread Out Your Questions Naturally

The worst thing you can do is bombard him with questions left and right. No one likes being in the hot seat and having to answer at rapid fire. The best thing you can do is to let your conversation flow dictate the questions you ask. Making your questions flow naturally within your conversations makes him more likely to feel engaged in your discussion.

Frequently Asked Questions

To achieve the ideal relationship, it is necessary to be able to ask the right questions at the right time. You will never know what makes your man tick if you don't. For those looking for more answers, these questions can help you out. Here are a few FAQs about questions to ask your boyfriend.

Do guys like answering random topics?

Random questions catch your man off guard, and while they can be endearing in some cases, they can also irritate. Generally, guys are OKAY with random topics. The trick here is to know when it is in the mood and when he isn't. Whether or not he is okay with your question will also highly depend on its weight.

Heavy "random questions" may not bode well when asked out of the blue and contribute to why men pull away. Instead, it's better to mention you have something important to ask him. On the other hand, light questions like who their celebrity crush is or what color they like best for a present are fine.

Why do girls love to ask their boyfriends questions to which they already know the answers?

Girls will ask questions they already know the answer to for two main reasons. One, she is trying to ensure she has the details right, especially if it has to do with date night preferences or a potential surprise for their man is in the works.

Two, girls repeat their questions if they want to know more about your answer. If an answer leaves room for more questions and wants to know everything, chances are a girl will continually ask until she gets the whole picture.

How often should you be asking your boyfriend some personal questions?

Asking your boyfriend personal questions is not something you should push for consistently. The best thing to do is ask questions one at a time on occasion. If you ask all your burning questions in one go, he could feel put off from answering and even get irritated at being hounded.

Can you test your boyfriend's love for you through his answers to your questions?

Formulating great questions can bring out his love for you, but doing so and being caught often leads to him feeling like you doubt his feelings for you. If you want to know directly how your boyfriend thinks about your relationship, it is best to tell him immediately that you are asking this question because you would like reassurance or a concrete answer.

More Interesting Articles To Explore

Texting your crush is a super fun way to have a conversation with them that is meaningful and fun at the same time. Read related blog posts for expert advice on confidently talking to your crush so you can start getting to know them more in a natural and engaging way!

  1. Find out how to ask a guy out with this related story on great conversation starters.
  2. Read my dating advice on how to play hard to get, so you make sure he is in for a more serious relationship.
  3. Check out this article on how to flirt with a guy using intimate questions that will have you both engaged in conversation.


The right questions to ask your boyfriend are well-timed and fit the mood and tone of the conversation and the relationship level you two are at. While it can be tempting to ask all your questions right off the bat, it's always best to move into it slowly and let him get comfortable with your conversations before going into deeper, more emotional questions. With that, you can naturally build your relationship upon a foundation of trust and respect.