120 Questions to Ask Your Boyfriend to Know Him Better (2025 Edition)

Editor’s Note (Updated for 2025): This guide includes fresh, meaningful, and flirty question ideas that fit today’s dating culture — from digital chats to late-night talks.

Intro:
Getting to know your boyfriend isn’t about big talks — it’s about the small, honest moments that build real connection. Whether you’re newly dating or years into your relationship, these questions help you spark deeper conversations, laugh together, and uncover what truly matters to both of you.

TL;DR: Use these 120 thoughtful questions to build emotional intimacy and spark fun, real conversations with your boyfriend. From love to goals to secrets — ask, listen, connect.

If you search for questions to ask your boyfriend online, you would most likely find articles that have anywhere from 60 to 200 questions you can ask your boyfriend.

A few years ago, there was also news that came out about the 36 questions you can ask that would lead to love with the final task being staring into your partner’s eyes for 4 minutes. So intense!

We’re here to make your life easy for you and we’ve narrowed them down to 20 questions guaranteed to help you get to know your boyfriend better.

Contents

Here are 20 questions you need to ask your boyfriend right now:
FAQ
- Key Takeaways

Here are 20 questions you need to ask your boyfriend right now:

1. What do you think aliens would actually look/be like?

We’ll start off light with a silly and fun question you can ask your boyfriend.

It’s also a good question to see what kind of imagination your boyfriend has. Not to mention, it’s also a roundabout way to find out if he is the kinda guy who is into conspiracy theories.

2. Should toilet paper hang over or under?

This question may sound like a small thing but it has huge repercussions. Most importantly, it is not about who’s right but that the two of you must somehow find a way to be on the same page about this.

If you’re worried that you cannot control your facial expression when you hear his answer, this is a good question for you to ask your boyfriend over text.

3. What is the strongest animal you could win against with just your bare hands and feet?

Here’s a somewhat cute and interesting question to ask your boyfriend. After all, not all questions have to be deep and probing.

An unexpected question like this will probably spark a lively discussion between the two of you and become a good memory for you two.

4. What names were ruined for you because you knew someone terrible with that name?

It’s a good question to ask your boyfriend especially if you’re planning on building a family together — because you already know which names are forbidden for your future children. 😆

5. If you had a secret lair like Batman or Superman, what would it be like?

Not only are you showing interest in this part of his life, but you also allow him to indulge in his fantasy and help you get to know him better.

This fun question is also a great way to secretly find out what to get him for his birthday or anniversary present.

6. What would be the absolute perfect day for you?

Here’s a question you can ask your boyfriend over text so that you can save his answer as a reference for future use.

Knowing what makes a day perfect for your boyfriend is one step closer to knowing what makes him happy.

7. If money was no object, where would you live and what would you do?

You would have probably seen this question before and it’s an interesting question to ask your boyfriend.

It would be fun to find out what he would do with his life if he had all the freedom in the world.

8. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

Another great question you can ask your boyfriend to get to know him better, his answer would show you how he thinks about his life and where it is heading.

9. What habits do you have that annoy other people?

If you noticed, the question isn’t about what annoys your boyfriend but which habits he has that would annoy people.
This is an interesting question to ask your boyfriend because it will make him reflect on his behaviour and let you know how he usually perceives himself.

10. What movie was so sad that you will never watch it again?

Here we want to tap into a feeling that is usually not expressed in guys — sadness but of course, they do feel it. Asking this question to your boyfriend will show you his more sentimental side.

11. What makes you angrier than it should be?

Usually at the beginning of relationships, you would want to be on your best behaviour and display the best side of yourself. This means it wouldn’t be easy to see the more angry side of your boyfriend.

This is another interesting question you can ask him so that you understand what ticks him off.

12. What did you learn a little too late?

Unless you’ve known your boyfriend since young, there is probably a lot of your boyfriend’s life you are not aware of.

This is an illuminating question to ask your boyfriend to find out what regrets and life lessons he has learned along the way.

13. What are you too hard on yourself for?

We tend to have very high expectations of ourselves and there is probably no one more critical than ourselves.

With this question directed to your boyfriend, you will learn about his insecurities and what makes him feel less confident about himself.

14. How often do you feel utterly worn down?

All of us have different limits to how much stress we can take in our daily lives.

When you ask this question to your boyfriend, not only will you know him better but you will also gain a little bit more empathy towards the struggles he might be going through.

15. Who was the most toxic person you’ve known?

Whether this person was an ex or someone in his family or workplace, your boyfriend’s answer to this question will help you better gauge what are the qualities he desires in his relationship with the people around him.

16. What do most people overestimate or underestimate about you?

As you progress in your relationship, you will slowly learn about your boyfriend’s strengths and weaknesses.

However, sometimes it is just easier to straight away ask your boyfriend what he thinks he’s good and bad at. You will also be able to find out how much he is aware of his own abilities.

17. What is the biggest sign of weakness in a person

This is an interesting question to ask your boyfriend because we all have our own stereotypes and prejudice that we project into the world.

You can also follow up this question with how would he react to this weakness if it was in someone that he loves? The answer will show you how kind and generous he can be.

18. What was the best thing about how your parents raised you?

It is no surprise that who we turn out to be is very much based on how we were brought up.

By asking this question to your boyfriend whether it’s face to face-to-face or over text, you will get to see how he feels about his parents.

You might even be able to catch a glimpse of what kind of parent he would become in the future.

19. If you could change one thing about me, what would it be?

Asking this question to your boyfriend could be similar to stepping into a minefield. You can’t really be sure what kind of answer you will hear.

But it’s a good question to ask your boyfriend because it will show you how he sees you. And sometimes change can be good.

20. If your life was a book, what would this chapter be called?

This question is more focused on your relationship and how he views this time with you in his life.

It can be a fun question but it can also be quite scary to hear your boyfriend’s answer.

These are also great questions to ask as conversation starters or to get to know someone on a deeper level.

If you’ve been on Sugarbook and you found someone you love to connect with — give these questions a try!

Also, look out for these conversation mistakes that you should avoid!

Fun Questions to Break the Ice
Perfect for new couples or first dates
Deep Questions for Emotional Connection
Talk about values, family, and trust
Flirty Questions to Keep Things Exciting
Add spark without crossing boundaries
Relationship Growth Questions
Discuss goals, communication, and love language
Random Yet Revealing Questions
Funny, surprising, and honest moments
Bonus: How to Ask Without It Feeling Like an Interview
Conversation starters and tips

FAQ

Q1. Why should I ask my boyfriend these kinds of questions?
Asking helps you understand his values, feelings, and experiences — deepening emotional connection beyond everyday chats.

Q2. What are the best times to ask relationship questions?
During relaxed moments — like date nights, road trips, or before bed. Comfort and timing make honesty easier.

Q3. Are flirty questions okay in a serious relationship?
Yes. Playful questions keep romance alive and show curiosity in your partner’s desires and emotions.

Q4. How do I avoid making the conversation awkward?
Start light and follow his comfort zone. Mix fun and deep questions naturally — it’s a chat, not a quiz.

Q5. Can these questions help fix communication gaps?
Absolutely. They open space for listening, empathy, and rebuilding emotional trust after misunderstandings.