21 Questions to ask your boyfriend (Questions game)

Whether you are in a new relationship or an old one; you’ve finally got the nerve to consider some questions to ask your boyfriend about your relationship and want to get to know him deeper.

By those burning questions that have been in the back of your mind for months or years.

You’re wondering if he loves you? How many girls he’s slept with before you? How did he feel when his last relationship ended? And whether or not he actually wants to go out with you again after you canceled last weekend because of a migraine.

If you think your relationship is getting stale or if you want to spice it up, maybe it’s time to mix things up and start asking each other some funny, dirty, juicy, serious, and deep questions.

This list of 21 questions to ask your boyfriend will provide you with the perfect opportunity to get to know him better and make sure that your relationship continues going strong well into the future.

You can also use this list as 21 questions game to ask your boyfriend.

After all, communication is key to any healthy relationship, so let’s see how this list can help you get started!

21 Questions to ask your boyfriend


These are some good list of questions to ask your boyfriend playing 21 Questions game:

1. Does it matter to you if Am I virgin or not?


This is one of the best tricky questions to ask your boyfriend to test his love, values and thoughts about sex.

It’s all in the way he answers this question that will show how much he really cares about you and what kind of person he is deep down inside.

A good guy will be concerned about who you are as a person, even if that means he’ll have to wait a little while for you to lose your virginity with him.

However, if you don’t like his response, take it as sportive and respect his views and needs just to avoid further conflicts.

Also read: 300 Questions to ask your boyfriend from funny to deep and juicy to sexy

2. What’s more important to you, family, friendship or love?


This is a great trap question to ask your boyfriend. The answer to this question can reveal a lot about his character and where he might end up spending most of his time.

Sometimes people think they need to choose between their relationships with their friends and families, but there’s no right answer here.

You should always try to keep everyone close to you – so make sure you make time for them too!

3. Would you rather date someone who was funny but wasn’t super hot or (vice versa)?


Ahah! This is such a great question to ask your boyfriend, because at the end of the day, everyone wants someone who makes them laugh.

If your guy has any sense of humor at all, then this is an easy decision for him: he’ll pick fun over everything else any day.

But, this question can be a great way to know what’s on his mind.

Also read: 21 Questions for a new relationship

4. Have you ever been in love before me? How many times have you been in love? And why did it end?


This serious question to ask your boyfriend can help you figure out his past and whether he’s really committed to you and see if he might cheat on you in the future.

Honesty is essential for building trust, so remember that when answering these tough questions. 

Observe his body language carefully while he talks about his previous relationships and pay attention to whether he mentions anything negative.

5. Do you remember the first conversation you had with me? And what’s your first impression of me?


The aim of this question is to learn more about the two of you.

Ask him if he remembers how nervous he was around you back then and what his first impression on you was.

That can tell you a lot about how comfortable he feels around you now, which will affect your relationship in the long run.

6. Would you leave me if I get serious health issues or disease?


A loyal guy will stay with you, no matter what. He won’t think about things like infidelity or breakups.

He’ll put himself through anything to make sure you’re happy, safe and taken care of.

This is a hard question to ask your boyfriend, but necessary for figuring out his true feelings about you. Pay attention to how he reacts and what he says to try and work out the truth.

Also read: 21 Questions to ask your crush

7. Where do you want our relationship to go from here?


We all want our relationships to last forever, so it’s normal for couples to worry about their future together eventually.

The key to making a lasting commitment is communication. So, sit down and talk to your partner about what you both want from the relationship.

Share your expectations and dreams together, and you’ll find that you’re both on the same page.

8. What’s one thing you would change about me?


This difficult question to ask your boyfriend will tell you a lot about his perception of you, but only if he answers sincerely.

Sometimes, we may feel embarrassed to share our weaknesses and flaws, but honesty is what builds a strong foundation for your relationship.

If he’s honest about the things he thinks you could improve, he’s willing to work with you to build a better you.

Also read: 20 Serious questions to ask your boyfriend

9. What’s your favorite TV show, books, or music?


Asking your boyfriend what his favorite movies, books and music tells you a lot about his personality and interests.

Watching TV shows together is a great way to spend quality time together and bond.

10. Who’s your celebrity crush?


A fun way to initiate a conversation and get to know your boyfriend a little better is to ask what his celebrity crush is.

Whether he chooses Emma Stone, Nicole Kidman, Taylor Swift or Selena Gomez, this question will give you some insight into his taste and what type of woman he’s attracted to.

Also read: 50 Trick questions to ask your boyfriend

11. When you were a kid, what did you want to be when you grew up?


This question to ask your boyfriend isn’t about the future, but about the past.

The answer to this question will tell you about his dreams, visions and what he’s passionate about. It’s also a good way to learn about his childhood, too.

12. What’s your most embarrassing moment?


Just like the other questions, this is a fun one to ask your boyfriend to lighten the mood and get closer to each other.

You don’t need to embarrass yourself in front of him, just let him share his most embarrassing moment and you’ll start laughing together!

Also read: 33 Trick questions to ask your boyfriend to see if he loves you

13. What are your thoughts on infidelity, affairs, cheating, breakup and divorce?


The controversial question to ask your boyfriend is about his thoughts on infidelity, affairs, cheating, breakup and divorce.

These topics might seem too heavy to bring up right away, but they’re important to discuss early on.

Find out how he sees these situations and what he expects from you before you decide to take the next step in your relationship.

14. When did you feel that I am the right one for you?


There is no right way to know if your boyfriend is really into you other than asking him directly in a strategic way.

The best way to figure out his feelings about you is to ask about the ‘right one’ and see what he says.

For example, How do you decide if a girl is right for you or not? This question definitely puts him on the spot, but the reward at the end makes it worth it.

Your man has been there for you since day one and knows you better than anyone else. His response to this question should be thoughtful and genuine.

Also read: 100 Trap questions to ask your boyfriend (persuasive and funny)

15. Are you ready to commit to a long-term relationship?


This is an essential question to ask your boyfriend. In a committed relationship, it can sometimes be hard to notice any changes, but the key to having a healthy and happy relationship is communicating.

This means sitting down and talking to your partner about what you both want from the relationship.

Talk about your expectations and dreams together, and you’ll find that you’re both on the same page.

16. Why is it that no one is as cute as you are when they’re angry at me?


This is a cute and flirty question to ask your boyfriend.

You’ll probably get a laugh out of it and learn more about his sense of humor.

In order to go everything smoothly in a relationship, a random naughty and sweet question to ask your boyfriend might help.

17. Do you want to have sex tonight?


Of course, sex is an important part of every relationship. But it’s always awkward to talk about how much you actually want to have sex with your significant other.

This is why you shouldn’t hesitate and make the first move instead.

Once you’ve opened up a dialogue, the awkwardness disappears and now it feels natural to talk about what turns you on in bed.

This is also a tricky way to know whether he is ready to be physically intimate with you before marriage.

18. If you had to describe me in three words, what would they be?


When dating someone new, it’s important to know how they perceive you. This builds a stronger foundation for your relationship.

If he’s honest about the things he thinks you could improve, he’s willing to work with you to build a better you.

This idea of working together to build something stronger is so powerful and motivating.

He doesn’t want to make excuses for you because instead, he wants to help you grow into who you’re meant to be.

19. Do you want me to remove your clothes every time you go for a bath? And shower together?


This is such a romantic and perfect question to ask your boyfriend. It’s even more romantic and exciting if you already spend a lot of time in the bathroom together and you already spend a lot of time naked.

Enjoy kissing each other’s favorite part, it’s important to explore different places on the body.

So once you know where your guy likes to fully be romantic with you, give them a little extra attention.

20. Do you think that people ever fall out of love? If so, why do you think that is?


The moment you fall in love, you fall head over heels. There are many reasons why some people fall out of love.

Maybe they were never truly in love to begin with and found someone better. Or maybe there was a huge fight and they needed some space.

Regardless of the reason, if you don’t think falling out of love is possible then you may be missing out on a person who loves you unconditionally.

So, this is one of the deep 20 questions to ask your boyfriend to see his reaction. 

21. What’s your opinion and future plans on love, marriage and having children with me?


End your discussion with this ultimate question. You will clearly know, What does he really want and expect from a relationship?

From your responses, you’ll start to understand his ideals and desires. The answers to this question are going to be completely personal and unique.

But be prepared to decide what to take in and what to let go.

And if you decide to take the plunge and do what’s right for you, then you’re set to experience a lifetime of happiness and blissful moments.


Final thoughts

There you have it, twenty-one questions to ask your boyfriend.

Keep in mind that these questions are all designed to promote open communication and foster a deeper connection.

And if you still have doubts about whether or not he feels the same way about you, consider taking a look at his social media profile.

Also, you never know what you have until you lose it. So, why not make sure that you’re getting everything you deserve by investing in your relationship now?

Ask those tough questions to get to know your guy and strengthen the foundations of your relationship.

Some questions, like Do you want to have sex tonight?, may lead to a good conversation. Other questions, like Are you ready to commit to a long-term relationship?, require a more serious answer.

These questions can help you get closer and learn more about your man and vice versa.

It is imperative that you take these answers seriously.


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Naveen Bommakanti

Naveen is Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry.

Naveen’s expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few.

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