42 Questions to Ask Your Boyfriend: Grow Your Relationship Gradually

Relationship Rules
09 Jun 2023
19 min read
42 Fun and Serious Questions to Ask Your Boyfriend

There are many games out there to ask questions – Hangman, 21 Questions, Never Have I Ever, Fact or Fiction, Charades, Guess Who. The list could go on and on. But will these games give you all the information to learn more about your boyfriend in the process of dating? Not always. For this, you’ll need the ultimate list of questions to ask your boyfriend instead. And here is it.

What you’re going to get here is a guide for the kinds of questions you should ask your boyfriend at each of three stages of your relationship. If you follow it, guess what? You won’t scare him off with questions like “How many children do you want?” Instead, you’ll have some fun and still get all the information you need to finally decide if he’s the one you want to spend the rest of your life with.

The questions listed below are divided into three categories, for each stage of your relationship – icebreakers, the early relationship stage, and getting into a serious relationship that looks like it will be long-term. The other thing to remember? Don’t just pepper him with questions. Spread them out over time, wait for the right moments, and be prepared to give your own answers to the same questions.

21 icebreaker questions to ask your boyfriend

First Dates: 21 Icebreaker Questions to Ask Your Boyfriend

Well, he’s not officially your boyfriend yet, but you already feel some attraction and have decided to explore where things might be headed. You might be chatting on a dating app, have had a date or two and have asked some of these, and you may be messaging or talking in between those dates. So now, this is the time for some fun, cute questions. They will give you insights into his personality, his sense of humor, and other stuff.

Here are some sample fun questions you can ask that may seem superficial but can still let you know if you want to move forward with him. Sometimes, you may want to provide your answer first.

For example, you might say, “Last night I dreamed that I won a billion dollars and was trying to decide what to do with it. What would you do?” And here’s the thing. When he tells you some things that he would do with that money, you’ll actually get some insight into what he values:

  • Will he travel?
  • Will he support a cause or two that are important to him?
  • Will he send all of his nieces and nephews to college?
  • Will he see that his parents have their best life ever?

You see? Fun questions can actually reveal a lot. Now some examples of icebreaker questions to ask your boyfriend.

1. When you were a kid, what was your favorite school lunch?

You can even add some follow-ups to this, “Do you still eat that today?”. This can turn into a discussion of food in general, and you’ll get some idea of his dietary habits.

2. What was your favorite Halloween costume?

Once he responds, you can expand the conversation to how he went trick or treating:

  • Did he go with friends?
  • Did they pull any Halloween pranks?

And from there, you can even move on to other holidays and how they were celebrated. You’ll get some insight into his family dynamics without having to ask directly.

You can always delve deeper into those dynamics with family members as the relationship moves forward. Asking what’s their favorite holiday is probably a good conversation starter too.

3. At an amusement park, what are your favorite rides?

In other words, does he like the extreme rides or the calmer ones? This may give you some clues about whether he is a risk-taker or someone who is more reserved and deliberate.

Another related question to ask your boyfriend is what his dream car would be. Does he choose a screaming fast sports car, a more reserved luxury car, or a more rugged all-terrain type? This can tell a lot about him.

4. Who’s your favorite fictional character from a movie or a book?

This is one of those fun questions to ask your boyfriend that will get a conversation going. Of course, you will give your favorite too. When you talk about what makes that character your favorite, you may get into a conversation about values and character traits that are important to each of you – it’s kind of a small compatibility test.

5. What’s your biggest guilty pleasure?

This is one of those cute questions that can start a simple, totally non-threatening conversation. It might be food of some type, but it also might be binge-watching a couple of Netflix series til 3 in the morning or taking a day off for opening day at the ballpark.

This is all pretty superficial, but you might get a little information about how he spends his spare time.

6. What’s the craziest thing you ever did?

Again, you’ll get a bit of insight into his personality. And maybe even his sense of humor. Did he skydive? Did he get a tattoo with his buddies when they were all a bit drunk on spring break?

A good follow-up question here is “What’s the weirdest thing you have ever done?”.

7. Tell me the best joke you have ever heard

So the point of this fun question to ask your boyfriend is obvious. You will get a bit of insight into his sense of humor. Did you find it funny too?

8. What are three things on your bucket list?

While this is one of those fun questions over dinner or drinks, it will also speak to his priorities in life:

  • Does he have a wanderlust for travel?
  • Does he want to be a millionaire and retired by age 40?
  • Does he want to own his own company?
  • Does he want to operate a wild animal sanctuary?

Listen to his answers – and don’t forget to share yours.

9. Do you have a celebrity crush?

You can share these and talk about what traits (physical or intellectual) you find especially attractive in them.

10. Are you a night owl or a day person?

This is one of those good conversation starters. Most people are combinations of these: they have to be awake and alert if they have a day job or are enrolled in a college program. But both of you may be night owls on the weekends and can talk about what you like to do then.

11. What’s a conspiracy theory you think might be true?

This might get into his politics a bit, but that’s okay. When you ask your boyfriend-to-be this kind of question, you want to check out if he is grounded in reality a bit, or if his belief in conspiracy theories is a bit “out there.”

And how about yours? Share one of yours if you have one.

12. What weird question do you want to ask me?

This is one of those fun questions to ask that will make him think a bit. But his question may reveal a lot about how he thinks. So, go with it and be ready with your answer, and then ask him the same question right back.

13. What’s the dumbest thing you’ve ever done?

This is one of those random questions to ask your boyfriend-to-be when you are just having a very casual conversation about some of your life experiences. It’s always good to laugh together, and this can be one of those times.

14. What’s your ultimate dream job?

This is a bit more serious question to ask your boyfriend-to-be, and you should listen carefully to his answer. You may gain some insight into his personality type.

15. Tell me two interesting stories from high school

You’ll get an idea of how he was as an adolescent, a time when values and goals are beginning to be formed that impact adult life. What he still finds interesting today from that time can be revealing.

16. Describe your dream house

This is just one of those fun questions to ask your boyfriend-to-be that can turn into a delightful conversation. Take it for what it is – one of those conversation starters that can have you just getting to know each other.

17. What was your favorite quality of the teacher you liked the most?

He may need to think a minute about this one. But his answer will tell you what he thinks is an important quality for everyone to have.

18. What was the best or strangest gift you ever got?

Nothing heavy here. Just something great or funny to remember.

19. What’s your ideal date night?

He’ll tell you his favorite thing to do on a date. Is it a favorite thing with you too?

20. What’s your favorite food?

If you like this guy, maybe you can have him over for dinner and fix it.

21. Do you remember your first kiss?

This is just a silly but fun conversation starter. Share yours too.

So, these are just some of the random questions that can be used when you first meet a guy you think you might be interested in. There are so many others, and you can find them on any number of websites. Choose the ones that are most relatable to you. Most are just fun questions, but each will be a perfect conversation starter. And many will give you some first-impression insights.

Early Relationship Stage: 15 Questions for Moving Forward

Now you’ve chatted, either online or in person, and you have been able to ask your boyfriend-to-be those non-personal questions that boost your interest in each other. So, it’s time to get more personal. You’ve had some real dates and are seeing where this relationship may go.

Now during this early relationship stage, it’s quite possible that sex may happen. And if both of you are feeling it, then that’s great. But you also want to know a lot more about this guy too. So, here are some questions to ask your boyfriend at this stage of the game.

Related reading: How to Be a Better Lover – Inside and Out

22. Are you willing to share your sexual health history with me?

Sharing health histories is pretty important if you are ready to have sex. And if he is willing to be honest and forthcoming with you, you must be too:

  • Have either of you had STIs in the past?
  • When was the last time you were each tested for STIs?

This may seem like the least romantic question to ask your boyfriend, certainly not your most favorite subject, but it is important. And he should understand why you are asking for and sharing this info.

But there are lots of other personal questions to ask your boyfriend at this stage too, to gain more insights on whether you two are on the same page on important things.

23. What’s the most embarrassing moment you had in your last relationship?

While this may seem somewhat unimportant, it’s not. Not only are you looking for the details of this most embarrassing moment, but you are also looking to see how he handled it. Maybe he discovered she was cheating on him, and it became public knowledge among his friends before he discovered it. How did he react? If he showed too much anger in his response to the situation, if he went for revenge, how do you feel about that? On the other hand, if he was hurt but moved on, is that a better response for you?

Related reading: Coloring the Grey Zone – Is Flirting Cheating?

24. Who is your best friend and what makes them that?

You want to know what qualities he sees as important in a friend and see if they jibe with the qualities you also see as important. You want a serious answer to this one. It’s one of the more important questions to ask your boyfriend at this stage in your relationship.

25. What is your idea of a healthy relationship?

Hopefully, you have done some thinking about this before you ask your boyfriend this question. And be certain to give him time to think about it before giving an answer. What you’re looking for are some of the key factors – stuff like mutual respect, honoring one another’s independence, honesty, trust, open communication, etc. You should share the “biggies” on what constitutes a healthy relationship and knowing your partner’s values in a relationship are critical.

Related reading: How To Maintain Your Individuality While In a Relationship

26. What are some of your hidden talents?

This is one of those fun questions to ask, and his answers might even be quite humorous – “Well, when I go to karaoke song night at a bar and hit the mic, I can get everyone out there talking a lot while I sing. So, I guess I’m a social director of sorts?”

Or he may surprise you with some more serious surprises when talking about a hidden talent: “Well, one thing very few people know is that I have published a book” or “I’m a self-taught construction expert of sorts, and I volunteer that expertise to Habitat for Humanity to supervise house construction.”

Those serious hidden talents may actually show you where some of his values and priorities lie or, at the very least, his outside passions and interests.

27. What’s your biggest pet peeve regarding women you have dated?

Here, you should get some insight into the behaviors or annoying habits that he finds distasteful in women he has dated. If, for example, he can’t stand it if a woman chews on her ice, and you do that, maybe now is the time to start breaking that habit?

Related reading: 21 Things Your Partner Should Never Say to You (and Vice Versa)

28. Do you like spending time with your family and extended family members?

With this question, you are digging into the relationship dynamics within his family:

  • Is he close to his parents and siblings?
  • How did his parents impact who he is as an adult today?
  • Does he have a favorite aunt or uncle who has been a major influence in his life?
  • Does he relate a favorite memory or two from growing up in his family?

And make no mistake about it. Family dynamics growing up impact adult romantic relationships.

29. What are your relationship deal breakers?

This is an important question before you go any further in this relationship. Because if you cannot live with his deal breakers it’s better that the relationship end now. The further you get into it, the more painful a breakup will be.

For example, if he states that a woman he marries must be a stay-at-home parent and you are on a career path that you have no intention of giving up, the best advice is to cut it now. Making the relationship work will be impossible.

On the other hand, he may have deal breakers that are totally reasonable to you – in fact, the same ones you have – dishonesty and cheating, for example.

30. What are your biggest fears?

Another way to ask this is, “What keeps you awake at night?” Most people by the time they are in an early relationship stage should feel comfortable enough to talk about their biggest fear. He may have fears that relate to the larger society as a whole – the environment, for example. Or he may have fears that are far more personal – a family history of cancer, for example, a career change that he may be making, or raising future kids. If you get a flippant answer to this one, he’s probably not being totally honest. Some relationship advice here? Give him some time – he may not feel he is in deep enough to reveal this part of his personal life yet.

31. What’s the biggest risk you’ve ever taken?

This can be one of those fun or serious questions to ask your boyfriend, often dependent on the context. If you are having one of those casual date nights, perhaps watching a TV movie thriller, his answer may relate to some physical risk.

But if you are involved in a serious conversation about investments or careers, you are likely to get a more serious answer. Would his risk-taking make you uncomfortable if you were in a long-term partnership?

32. What would be your personal hell?

Have your answer ready on this one. To keep it light, you might want to say something like, “My personal hell would be spending eternity as a telemarketer. What’s yours?”.

33. Do you believe in love at first sight?

Love at first sight does actually happen, but it is not too common. Usually, it’s infatuation or just plain lust.

Related reading: When You Love Someone – Do You Really Know?

His answer probably does not impact your relationship now because you have been seeing each other for a while now. But even in the early stages of a relationship, if he is already saying the “love” word, ask yourself how you feel about that.

34. What’s your favorite outfit that I have worn?

This may seem pretty superficial, but it may tell you something about what he appreciates in the dress style of his woman. Does he prefer you in modest or sexy stuff? And is that something you feel comfortable with?

Related reading: The Cutest Ideas for First Date Outfits for this Season

35. What’s the biggest lie you’ve ever told?

We’ve all told whoppers. But knowing the details will give you just a bit more information about his behaviors.

36. Do you think a long-distance relationship can work?

This is one of those questions to ask if you see separations in your future. Maybe you will be traveling for work. He has to be okay with this. It’s only a question to ask if separation is a possibility.

Related reading: Does Distance Really Make the Heart Grow Fonder?

Things Are Serious: 6 Questions to Ask Your Boyfriend

It’s time to get into some deep questions because you are certainly thinking about a long-term relationship here. You’ve been sexually active for a while, you are in a primarily monogamous situation, and you are looking at the possibility of spending your whole life with this guy. You will be asking intimate questions about your boyfriend’s relationship history, about how your relationship is going, and your future. Here are some things you’ll want to know.

37. How many past relationships have you had that were serious?

Related questions will be “How many sexual partners have you had?” and “Why did your serious previous relationships end?” These kinds of intimate relationship questions to ask your boyfriend may require some longer conversations and should be in a quiet environment.

Of course, you are willing to answer the same questions. But your other responsibility (and his) is to listen without judgment or criticism. Answers to intimate questions require a comfort level.

38. As a romantic partner, what would you like more of from me?

None of us is a perfect partner, and no relationship will be in a honeymoon phase forever. You’ve been together long enough now, to be honest about what you may want from each other that you are not getting enough of:

  • Is it not enough love language?
  • Does he need more intimate moments in your sex life?
  • Is it more affectionate physical touch?
  • Does he want deep conversations more often about dreams and goals?
  • Does he want you to express love for him more often?

You must be prepared to receive his answers without taking offense or making excuses and rationalizations. This is one of those deep questions to ask your boyfriend that you are prepared to act on.

39. What’s your ultimate bedroom fantasy?

This is one of those juicy questions to ask your boyfriend that will let him tell you about his ultimate pleasure in the bedroom and his favorite sex position, and any other favorite thing he wants in the sex department. You’ll get some ideas about how to spice things up for him.

Related reading: The Making of a Sexual Goddess

40. What’s the best mistake you ever made?

So, this is not one of those romantic questions, but it will tell you a lot about how he deals with big goofs. Did he take responsibility? And what was the most important thing he learned from it?

41. How do we keep this happy relationship happy?

This is one of those relationship questions that will lead to a solid discussion of what both of you can do, individually and together, to keep your love alive and well.

42. What are your plans for our future?

Does he want marriage and a family? Is he ready to share all aspects of his life with you? It’s important that you are on the same page here.

That’s a Lot to Take In, But It’s Worth It

Yes, it is, and this is not even a full list of all the questions to ask your boyfriend. In the end, you have to decide what questions to ask to get the information you need to know if you intend to move into a long-term partnership or marriage. But these are a start. Onward!

Dating Tips Author
Shelly Standford
After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!
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