Serious Questions to Ask Your Boyfriend – How Deep is Your Relationship?

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By David

Every relationship is different. You cannot generalize. But one thing that is common in every relationship is communication. Lobsang Tenzin says “Communication will bring understanding and understanding will cause harmonious mutual relationships which can establish peace and stability”. So, what are some serious questions to ask your boyfriend?

Let’s start with a simple one, how well do you know your partner? What does your partner like? What he dislikes? Does he have any regrets, passions, trauma, dreams, and more? There is always room for improvement, no matter at which stage of the relationship you are. An open and honest conversation will always bring you closer. You can build trust and mutual understanding.

The power of questions

It is important that you enter the communication with an open mind. Allow yourself to be vulnerable and practice empathetic listening. You have to be ready to listen, but you also have to ask the right questions. And of course, at the right time. You can use them to realize breakthroughs in important areas of your life.

The right intimate questions to ask your boyfriend will help you understand what he loves, likes, and what he hopes for.

When and What to Ask

The right serious questions to ask your boyfriend are just one part of the equation. The other part is the timing. For example, you are walking around in the park, having fun, and asking a question like, where do you want to get buried if you die is not suitable. Or, you are in bed, and you ask something inappropriate.

The science of intimacy is knowing what and when to ask. There are different stages of your relationships. Depending on which stage you are, you can ask the right questions. And thanks to the deep questions to ask your boyfriend, you progress through the stages. You can start as friends, move to lovers, and then, companions.

  • Stage 1 is when you get to know someone’s general personality traits. You need to find out where does your boyfriend stands on openness extroversion, agreeableness, and conscientiousness
  • Stage 2 is personal concerns when you look to understand his goals, values, and motivations in life. You can get a broader picture of his decisions, attitudes, and everything else that shapes his life
  • Stage 3 is the last stage when you truly know someone. Here, you can start asking stories about themselves, stories that made sense through the journey

Think of the first stage as an easy and typical conversation. The second stage is when you live with someone, travel with him, and share experiences. For the last stage, you need the right questions in a safe place. With that in mind, let’s take a look at some serious questions to ask your boyfriend.

General Questions

We start off with some of the general questions. You want to know more about someone. You like him physically, but you need to get to know him. Think about preferences, what you like about each other, and more.

Here are some ideas.

  • What is the first thing you noticed about me?
  • What makes me different than other girls?
  • How do you describe me?
  • Do you have a type?
  • Do I fit your type?
  • What was the first thing you thought about me?
  • What qualities you want or look in others?
  • How much do you look for physical attraction?
  • How should I describe you?
  • Name three wishes you would like me to help you
  • What do you do for fun?
  • How often do you talk to your friends about serious things in life?
  • Do you make a fuss about special occasions?
  • Did you have a role model growing up?
  • What was your career choice as a kid?
  • What is your favorite holiday?
  • What makes you feel better on a bad day?
  • You are in an amusement park, what is one ride you have to go on?
  • What is the best present you have received?
  • Did you have any pets as a kid?
  • What was your favorite toy as a kid?
  • Do you have a favorite karaoke song?
  • Do you have favorite scents?
  • What is your favorite sound?
  • What do you do on a rainy day?

Questions on Life

Now, you can also continue asking questions about his thoughts on life. You want to get a better understanding of his values and goals.

  • Is there something you do not want to do ever again?
  • What gets you nervous?
  • Say you win the lottery, what is the first thing you would do?
  • Do you think things happen for a reason?
  • Do you believe in destiny and karma?
  • Let’s say you wake up tomorrow, and all your fears are gone, what would you do first?
  • What do you consider unforgivable?
  • What should a healthy relationship provide for the people in it?
  • What would you say to your younger self?
  • How does your perfect day look like?
  • Do you follow your head or heart when making decisions?

Questions on the relationship

Now, here you can throw in some romantic questions to ask your boyfriend. You want to know where your relationship stands, how it started, and where it goes from here.

  • What makes you happy in our relationship?
  • How would you describe our relationship?
  • What is your fear about the relationship?
  • Do you have a favorite memory of us?
  • What is one thing that is different in me and you that you love?
  • What is one similarity we have that you love?
  • Where is your favorite place?
  • Do you think our relationship lacks something?
  • What is one personality trait you love about me?
  • What would you miss if our relationship ended?
  • When was our most vulnerable moment?
  • Can you tell me a secret you haven’t told me before?
  • How do you want to receive affection?
  • You have a magic stick, and you can change one thing about our relationship. What would it be?
  • What makes us work so well together?
  • How do we balance each other?

Questions about the future

Now, you might think these questions look a lot more like questions you get on a job interview. These are crucial. Do not put your boyfriend in an uncomfortable position. Do not make him feel like he is under investigation. Or worse, at a job interview, he probably won’t win. Be careful and gentle, and you can find out a lot.

  • Where do you see yourself in a couple of years?
  • What do you think the future holds for us?
  • How do you see us together?
  • What are your thoughts on having a family?
  • How would you raise our kids?
  • What are your ideas for retiring?
  • Do you have something on the bucket list we can do together?
  • What is one thing you want to achieve in life?
  • What do you look forward to about getting old?
  • Do you want to learn something more in the next few years?

Questions on his past

When you know your boyfriend, you can start asking some intimate and vulnerable questions. You want to find out more about his past. Now, he is your present and future. But it is important to know where he comes from.

  • What is one accomplishment from the past year you are proud of?
  • When was the last time you were out of your comfort zone? How did you feel?
  • What is your best memory?
  • When was the last time you cried?
  • When was the last time you felt vulnerable?
  • What is the biggest lesson you learned from your past relationship?
  • How did you overcome setbacks?
  • Let’s say you can change one thing in history, what is that?

Fun and cute questions

You do not have to be serious at all times. Sometimes, you can throw in some fun questions in your serious questions to ask your boyfriend. Your partner probably has great stories to tell. It is your job to get him to talk.

Let’s check some fun questions to ask your boyfriend.

  • You can choose anyone, who do you want for a dinner guest?
  • If you are famous, who are you?
  • If you can gain one superpower or ability, what would you choose?
  • You have a crystal ball, and it can tell you anything about you. What do you want to know about your future?
  • Tell me some embarrassing moment of your life
  • If you can save one item in a fire accident in your home, what would you save?
  • Do you have a crush on a fictional character?
  • Do you believe in ghosts?
  • Name three foods you can eat for the rest of your life
  • Have you ever been in a prank? Or have you pranked anyone?
  • Who would you want to be for one day?
  • Do you collect anything?
  • Do you have a theme song?
  • What is one tattoo you would get today?
  • Have you tried to invent something?
  • You can change your name to anything, what is your pick?
  • If you can bring one person back from the dead, who do you pick?

Deep Questions

We had cute questions to ask your boyfriend. We also had fun questions to ask your boyfriend. It is time to get serious. Here are some deep and serious questions to ask your boyfriend. These help you understand whether you two belong together.

  • How long was your longest relationship?
  • Why did you end your past relationship?
  • Have you ever been engaged?
  • Do you want to get married eventually?
  • Have you ever lived with someone?
  • Do you think money can buy happiness?
  • Do you have a dream job?
  • What is one thing you want to accomplish in life?
  • Do you hold grudges against people?
  • What are you afraid of?
  • What is your love language?
  • Have you ever been in an abusive relationship?
  • Have you ever struggled with an addiction?
  • Do you think a relationship can come back from cheating?

Do you Want to Get Dirty?

We talked about what are some deep questions to ask a guy. But, if you want to get dirty and flirty, we have some other ideas too. You can use these cute flirty questions to ask your boyfriend to spice up things. Sex is a topic you have to talk about.

  • How many times would you have sex in a week in an ideal world?
  • What is one thing you always wanted to try?
  • Have you ever had a threesome?
  • Do you want to have a threesome?
  • Have you ever been attracted to a man?
  • How did you lose your virginity?
  • Tell me one sexual fantasy
  • Where is your favorite place to have sex, outside of the bed?
  • How do you feel about porn?
  • What kind of porn do you like?
  • Would you watch porn with a girlfriend?
  • What is your favorite sex position?
  • What is your least favorite sexual position?
  • Tell me a weird thing that turns you on
  • If we try role play, what do you want?
  • What is your favorite part about sex?