Deep Questions To Ask Your Boyfriend

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Looking for Deep Questions To Ask Your Boyfriend?

If you were to ask 100 ninety-year old men and women what the key to a successful relationship is, many of them will probably tell you “communication”.

You’ve probably heard the term “communication is the key”, and we firmly believe that over here. That’s why we love relationship question games.

image reads "deep questions to ask your boyfriend" with couple laughing, laying down in a field.

If you want your relationship to stand the test of time, it’s important that you and your partner connect on a deeper level. Open and honest communication will allow you to connect intellectually, spiritually, intuitively, and emotionally, which will essentially be

what keeps you together through it all. 

101 Deep Questions To Ask Your Partner

So today, we’ve put together 101 deep questions that you can ask your partner to get to know each other on a deeper, more intimate level. 

  1. What was your childhood like?
  2. What was your biggest fear as a child?
  3. How did your school years affect who you are today?
  4. What was the biggest lesson you ever learned as a child and how did you learn it?
  5. What do you admire most about your parents that you’d like to take forward with you?

  1. Is there anything about your parents that you wish you could change?
  2. When your parents get older, what will you do to care for them? 
  3. Do you want to be a parent? How many children do you want?
  4. What do you think your parenting style will look like?
  5. What was your first serious relationship like?

  1. Did you ever think you were in love with someone when you weren’t?
  2. Have you ever been hurt in a relationship?
  3. Have you ever been the one to hurt someone in a relationship?
  4. What did you learn from your last relationship?
  5. Do you believe in love at first sight?

  1. What do you think it means to “be in love?”
  2. How do you show a partner that you love them?
  3. What do you think is the key to a successful relationship?
  4. What do you most look forward to in our relationship?
  5. Is there anything you would like to change about our relationship?

  1. How can we work to consistently improve our relationship and communication?
  2. Is there anything you need from me that you aren’t receiving right now?
  3. Do you think there is ever a scenario where it’s okay to lie?
  4. How have your values changed over the last 10 years?
  5. What do you think is important in life?
  1. What is your best character trait?
  2. What is your worst character trait? What can we do to try to change that?
  3. What do you think my best trait is?
  4. What is my worst trait? How can we work to change that?
  5. When were you most disappointed in yourself? How did you come back from that?

  1. When have you been the most proud of yourself?
  2. Have you ever faced depression? How did you overcome it?
  3. Have you ever battled any addictions?
  4. Who is your biggest role model? What is it that makes them so?
  5. What motivates and inspires you?

  1. What can I do to motivate you?
  2. What are your long term goals?
  3. Is there anything in life you are ashamed of?
  4. What’s your biggest regret in life thus far?
  5. What do you think about friendships with the opposite sex?

  1. What do you consider unforgiving in a relationship?
  2. How do you think couples should handle financial division?
  3. How do you think couples should handle chore division?
  4. What’s the most important aspect of a relationship?
  5. How do you handle conflict in a relationship?

Deep Questions To Ask Your Significant Other

  1. What gives you anxiety?
  2. What strategies do you use to relax when you are feeling stressed out?
  3. When you are upset or stressed out, what do you need from me? Should I give you space or comfort?
  4. If the world was going to end in a month from now, how would you spend your time?
  5. What would you do if we won the lottery tomorrow?
  1. If you had the opportunity, what would you do to change the world?
  2. If you could start a charity organization, what would you do?
  3. What do you think the world needs more of?
  4. What do you think the biggest problem is facing the world today?
  5. If you had the opportunity, would you choose to go back in time or forward in time?

  1. If you could go back to one moment in your life, what would you choose and why?
  2. Have you ever lost someone that you love deeply?
  3. What’s something that you’re happy you will never have to do again?
  4. What do you think a “healthy” relationship looks like?
  5. Do you believe in fate?

  1. Do you believe in God?
  2. Do you believe in religion?
  3. Do you think that everything happens for a reason?
  4. Do you believe in an afterlife?
  5. What’s been the biggest blessing in disguise for you?

  1. What are deal breakers in a relationship regardless of how long you’ve been together?
  2. If you could write a note to your younger self, what would it say?
  3. If you could write a note to your older self, what would it say?
  4. What makes you feel alive?
  5. Do you believe you should follow your head or your heart when making decisions?

  1. What’s your biggest fear about our relationship?
  2. What’s your favorite memory of us?
  3. What made you fall in love with me?
  4. At what moment did you know you were in love with me?
  5. Is there anything you’re afraid to ask me?

  1. Are there any secrets you’ve been afraid to tell me?
  2. What’s your love language? Do you feel like I meet the needs of that language?
  3. Why do you think our relationship is unique from other peoples?
  4. What is our biggest strength in this relationship?
  5. What is one thing about me that you never want to see change?

  1. Is there anything you’ve dreamed of doing but haven’t done yet?
  2. What’s your most embarrassing moment in life?
  3. What’s your most prized and valued possession?
  4. What do you want people to remember most about you when you die?
  5. When was the last time you felt vulnerable?

  1. What would you consider to be the biggest turning point in your life?
  2. When was the last time we got out of our comfort zone together?
  3. If you had the ability to change history, which part would you rewrite?
  4. Do you consider yourself to be a jealous person? How does that play out in your relationships?
  5. Have you ever been in an abusive relationship?

Deep Relationship Questions

  1. Do you consider me to be your best friend?
  2. Do you have any regrets in our relationship?
  3. How do you think our love has grown over the years?
  4. Do you like the relationship that I have with your parents?
  5. Are you comfortable with my parents?

  1. Do you think that our relationship has enough passion?
  2. What are your wildest fantasies?
  3. Would you prefer me to lie to you or tell you the cold hard truth?
  4. What would you like to do more of together?
  5. Do you feel comfortable sharing your secrets and problems with me?
  6. Do you see our relationship standing the test of time?

Use these questions to open the lines of communication with your partner and to bring the two of you closer together than ever before. 

Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.

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