deep questions to ask your boyfriend

88 interesting deep questions to ask your boyfriend 2021

Life is different for everyone, some learn the hard way, some predict their actions and some are adviced. But, for men things are equally difficult as for women if not more.

If you’re a girlfriend/partner to someone, you need to go for deep questions to ask your boyfriend or partner.

That will not only let you know what kind of a person they are but will also add up to respect and trust towards each other.

Besides, there are conversations which no one has with man, if you could have them you would be the closest to that person that very moment. This adds upto their life. You would be wondering how to start, right?

How to start with deep questions to ask your boyfriend/partner?

deep questions to ask your boyfriend

This is one of the parts where most people lack, not knowing what your man is thinking is what makes you not a good partner. Before starting with deep questions to ask your boyfriend/partner, you need to keep a few things in mind.


  1. Listen properly: Be a good listener, you might be listening to such incidents or conversations which no one has known before. If you’re the one who their boyfriend or partner is telling, you mean something to them.
  2. Try to understand their point of view: Before saying anything to them for anything they told you, keep in mind what they would or will react to you. Smashing bricks of your own understand, try to understand their perspective.
  3. Be serious about the conversation: How would you feel if someone mocked your conversations which are a big part of your life, disappointed or angry or frustrated, right? The same happens with the person who is sharing something with you.

As soon as you keep these three key points in your mind, you’re ready to for deep questions to ask your boyfriend or partner or crush.

Deep questions to ask your partner

deep questions to ask your partner

After answering what to keep in mind, you can proceed with the questions to ask your partner.

Besides, you would be brainstorming questions, what to ask, how would he react. Rather than thinking of these questions, think what were those moments you didn’t want to share with anyone.

Let’s rephrase it, what’s that thing he is keeping to himself. Want to know, here are deep questions to ask your boyfriend which will help you in it.

  1. What was the turning point in your life?
  2. What did you realize when you hit the lowest in your life?
  3. Is there something that makes you vulnerable?
  4. Which was the moment when you felt worth it?
  5. Have you achieved what you dreamt of?
  6. When was the last time you felt embarrassed?
  7. Why don’t you socialize?
  8. Is there anything that bothers you when no one’s around?
  9. What is your goal?
  10. What exactly is a need of your life?
  11. Have you ever gone against your ethics?
  12. What is that one quality you hate about a person?
  13. How did you deal with you being at the lowest?
  14. What became the reason for you to work every day?
  15. Has something changed along the way?
  16. Which is one major change you appreciate in yourself?
  17. Do you want to be treated?
  18. Who is the one person you can trust?
  19. What is your biggest turn off?

RELATED: Sexually intimate questions to ask your partner

These are some deep questions that can lead to an amazing conversation that will unfold a character and struggle of a person. Building trust and earning respect is what not everyone is capable of. Being a good listener is what can help you get both.

Questions to ask your boyfriend about the past

questions to ask your boyfriend about past

We all struggle, face problems every day. Sometimes it could be big enough to break you down, or you could be prepared enough to break the problem down. Depends on the personality of a person how they deal with it.

But what deep questions to ask your boyfriend that would make the conversation interesting about the past?

Here are we to help you our with that.

  1. What’s one thing which you regret the most?
  2. Do you appreciate anything which happened in the past?
  3. When did realize, it was not worth it for you?
  4. How did you overcome the fear of ….?
  5. Is there something which you didn’t tell me?
  6. What as that one moment when you hated yourself the most?
  7. Which is one thing/moment you want to forget?
  8. If you got a chance to change anything in your life, what it would be?
  9. When were you the angriest?
  10. What was the biggest lesson you learned in your life?
  11. How did you want your life to be when you were a kid?
  12. Did anything break you inside?
  13. What is the biggest lie you have been telling people?
  14. Were you jealous of anything?
  15. Do you still think of your EX?
  16. Who became your biggest inspiration?
  17. With whom did you share your life when no one was around you?
  18. Did you ever break someone’s heart?
  19. When you were growing up what superpower you needed?
  20. Have you ever regretted your decision?

RELATED: Intimate deep questions to ask your boyfriend

Questions to ask your boyfriend about the future

questions to ask your boyfriend about future

As important as the past become, future comes with more responsibility and expectation which you might have. But, with that deep questions to ask your boyfriend also change.

Why? Because the perspective of a person decides who they want to be. And this is what makes it possible. A VISION.

  1. What do you want to become?
  2. Which is the one trait you want in your life?
  3. How do you think you would be treated in the future?
  4. Will money change major things in your life?
  5. Is there something you won’t want in your life?
  6. At what stage you would stop working?
  7. Can you think of one thing which you would love to have?
  8. If you could write someone’s future except your who would you write?
  9. What is the first thing you would do if you got everything you wanted?
  10. What lesson would you like your loved ones to keep in mind?
  11. Have you found a way to reach your dreams?
  12. How do you want to be remembered?
  13. What are your thoughts about family?
  14. When you’re going to accomplish your bucket list?
  15. How do you want to retire?

RELATED: Romantic questions to ask your boyfriend

These questions will not only add pages to your love life but also add some memories which you could cherish your lifetime.

Deep questions about the relationship

deep questions about relationship, deep questions to ask your boyfriend

Honestly, there are a lot of things which go around the relationship. Going with deep questions to ask your boyfriend is only one part of it.

Being one of the major part of relationship it becomes important for a couple to know their partner’s opinion and move accordingly.

  1. When was the first time you realized you were in love with someone?
  2. What’s your favorite thing about us?
  3. Will we last long?
  4. Do you have plans for us?
  5. Are we going the right way?
  6. What could make our relationship better?
  7. Do you think we could go through worse together?
  8. What do you fear the most?
  9. Have you thought of giving up?
  10. Which trait you want to change about us?
  11. Did you think of having kids?
  12. When was the last moment you were proud of yourself?
  13. What would you be doing if we were not together?

RELATED: Intimate questions to ask your partner

These are some deep questions to ask your boyfriend, before asking these questions remember to share your experience which will keep the conversation interesting. Besides, you can ask these questions to any person you’re comfortable with.

This will not only get you to know a person closely but also will let you know the personality a person adheres.

Some of these questions become universal, you can ask to a friend/partner or anyone with which you share a good bond and you want to take that relationship a step further.

PRO TIP: Never ignore the facts the person keep in their conversation.

If you do this, you could spoil the relationship which you share along with the person. Adding to this, you’ll leave a negative impact on the person you had a great bond with.

Deep Questions to ask your boyfriend in a long distance relationship

Being in a long distance relationship and sharing a strong bond is really hard. Unlike any other relationship, it requires more patience and trust. Being apart from each other and having no choice but to trust each other is risk. But if you get along with it, every moment becomes worth it when you spend time together.

Here are some deep questions to ask your boyfriend in long distance relationship.

  1. What would be the first thing you do when we meet?
  2. Which is the best thing you like about our long distance relationship?
  3. Is there anything you hate about is being in a relationship?
  4. What makes you remember me everyday?
  5. According to you, is this relationship worth waiting?
  6. What makes you work for this relationship?
  7. How would you spend your perfect day with me?
  8. Did distance become trouble for you at any point of time?
  9. When was the last time you had to keep things from me?
  10. Have our timings ever interrupted your schedule?
  11. When did you realize we were meant to be together?

Additional interesting deep questions to ask your boyfriend

What could be the best thing you could ever get as cheery on the top.

Here are some additional interesting deep questions to ask your boyfriend which not only makes things better between you and your partner but also help you get hold of them sooner or later.

  1. If you got one day to do anything what would you do?
  2. Have you accomplished your goals?
  3. When was the last time someone appreciated you?
  4. Have you ever felt being left out?
  5. What is the funniest moment you remember that embarrassed you?
  6. Which is the worst part of your life you haven’t told anyone?
  7. Is there something you have kept to yourself?
  8. How do you overcome your stress?
  9. Did you ever feel jealous of the men around me?
  10. When was the last time you were furious at someone and let it go?
  11. What was the wisest thing you ever said or did?
  12. Do you think of family?
  13. What is the one thing you regret the most?
  14. Are you good at expressing yourself?
  15. When was the last time you felt scared?
  16. Is there anything you want everyone to know?

What deep questions should I ask my boyfriend?

1. What did you think of me when you first saw me?
2. How did you knew you were in one?
3. When did you realize I was the one?
4. Is there something you’re hesitant to tell me?
5. Do you have a favorite memory of us?
6. Have you ever put our relationship at stake?
7.How long do you think we will last?
These are some of the deep questions to ask your boyfriend anytime and anywhere you want to. But the best place to ask it is a date or when you are spending some time alone.

What are some deep relationship questions?

1. Have you ever hidden something from me?
2. Did you do something which you regretted later?
3. Do you think ‘I’m am the one?’
4. What do you want to change in us?
5. Who is the closest person to you?
6. Who is that one person you don’t want to loose?

What questions would you ask your boyfriend?

1. Do you think we will last?
2. Did someone ditch you?
3. Which is the one thing you’re scared of?
4. What is the perfect day for you?
5. What is your ideal woman?
6. Has anyone impressed you at one go?
7. How did you feel when you first approached a girl/lady?
8. How did your first kiss go?

How do I start a deep conversation with my boyfriend?

Before going with deep questions to ask your boyfriend make sure you have a private time or place where you can talk about it. Talking about it in a group or publicly might not help you have a good deep conversation because people have different opinions.
1. Ask for insecurities, open about your insecurities too.
2. Know what was the best and worst phases of their life.
3. Keep cracking jokes to keep the conversation interesting.
4. Add some elements which can make conversation going.
5. Don’t push the conversation, just go with the flow.
6. Share, express, and ask for opinions that would help you (this will add trust and respect to your relationship)
Follow these steps accordingly and you can have the best deep conversations of your life with the person you want to.

Leave a Comment

Your email address will not be published. Required fields are marked *