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50 Serious Questions to Connect With Your Boyfriend

Updated on September 29, 2019
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I've been through too many failed relationships and finally found the one. I enjoy writing about relationships and spiritual connection.

Are you ready for a serious relationship?

Both of you have been dating for some time. All is going well and you feel like it is time to kick the relationship up a notch.

Love, acceptance, respect, security and passion are all checklist items in a serious relationship. These are basics wants. Assurance of safety and depth of a relationship are the next level of a serious relationship. So, asking some deep questions are essential. By knowing him better, what kind of person he is, and the expectations from each other, both of you can align your moral and core values to go into a long-term relationship.

5 Steps to Make Him Have a Heart-to-Heart

It is really awkward to jump into an intimate conversation with anyone without warming them up. Being able to connect with him at a deeper level is a delicate task especially if you know he is the type who will freeze when talking about personal matters.

The thing is, there is no such thing as a deeper relationship without really knowing the person. So how do you lead him to the path of a heart-to-heart?

Step 1: Prepare your questions

Preparation is key to an emotional connection. Start listing down all the questions that you would like to find out from him. A couple of things to take note:

  • Ask open-ended questions to expand the conversation. (“Do you bite nails?” - Yes/ No and this will be the end of the conversation. Instead, ask him, “How do you upkeep your personal hygiene?).

  • Avoid leading questions like “Would you feel incomplete without me?” or “Thai food is nice, what do you think about Thai food?”.

  • Avoid questions that lead to a dilemma: “If you have to choose between your mother and me, who would you choose?”. Obviously, when facing you, he will say...you.

Step 2: Set the stage

Don’t ask deep questions when he is driving halfway or in the middle of a meeting. Set a stage to have a proper conversation. Have a romantic candlelight dinner at your place, a picnic under the stars. Fill up his stomach, have a few glasses of wine and get in a chill, reflective mood to get a deep conversation going.

Step 3: Be open to what he shares and be ready to share

It is absolutely crucial not to judge his answers or get defensive. When a conversation ends up this way, it is bitter and it will be hard for him to share again.

Also, you have to share yours to get him to share his. A conversation is a two way street.

Step 4: Take a break if needed

Be mindful of how the conversation is going. If he is giving curt answers or do not wish to share further, take a break or stop the conversation. Perhaps he is not ready to share at the moment. Surprisingly, the man is likely to re-initiate the conversation. This is a very good indication that he is ready to share.

Step 5: Show appreciation

Give him a kiss or show how much it means to you when he shares his personal side to you.

Lastly, repeat the process until you are satisfied that you have a deeper relationship!

50 Serious Questions to Ask Your Boyfriend

10 Questions About Him

What is easier to start off than talking about himself? Start off with a few light-hearted scenario based questions and move to heavier topics like his personal experiences and opinions.


  1. If you can have a superhuman power, what power would you want to have?

  2. What ability would you prefer to have? The power to change the past, or to have the power to make the future better?

  3. If you lose one of your five senses, which one would you want to lose?

  4. How were you like when you were younger (in high school, college or even elementary school)?

  5. Who is the female celebrity that you support the most and why?

  6. If you have a bad day and is too irritated, what would you do to make the rest of the day better?

  7. What kind of clothing do you like to wear?

  8. What is the one thing that you like the most of yourself?

  9. What is your pet peeve?

  10. According to you, what is your perfect day?

5 Questions About the First Impression

Questions about his first impression of you is a good gauge on how your boyfriend perceives you. At the same time, it helps to rekindle the love fire that started off everything.


  1. How did you feel when you met me the first time?

  2. What is that special thing in me that attracted you?

  3. Why did you decide to chase me (or vice versa)?

  4. What kind of girl did you think I was when you first met me?

  5. If we can repeat our first meeting, is there anything you want to do differently?

5 Questions About You

Take the chance to find out how well he know you with the following questions:

  1. What kind of lifestyle do you think I have?

  2. What are my enjoyable habits that irritate you most?

  3. What are the types of songs I will like?

  4. What are the 10 questions that you want to ask me?

  5. What do you think about my financial position or goal?

20 Questions About Your Relationship

Find out what he view his relationship with you, marriage and sex.


  1. What do you think what is that key that makes a relationship successful?

  2. What do you think about our relationship?

  3. According to you, how should a romantic date should be?

  4. What’s your favorite way to show affection?

  5. Was there a moment in our relationship that made you feel special?

  6. What is a deal breaker for you in a relationship?

  7. If any of us feel frustrated, how will you attempt to get out of that?

  8. How serious would you think our relationship will be within 6 years?

  9. Do you prefer to have a joint account in case of our relationship? Why?

  10. What do you think about our financial situation right now?

  11. What do you think about maintaining space in a relationship?

  12. Which parts of our relationship do you want to maintain privacy?

  13. Are there any privacy boundaries that you would like to establish for our relationship?

  14. What do you think of marriage?

  15. What are your ideas of monogamy and polygamy?

  16. What do you think about your (or my) parent’s marriage. Are there lessons we want to learn and improve on?

  17. What is the sexiest thing that you find in me?

  18. What is that wildest way you to have on the bed?

  19. If you give yourself and me a porn name, what would it be?

  20. What is your horniest moment?

10 questions about your Ex, Friends and Family

  1. If you see my ex in a bar that you regularly visit and he moves to you, how would you react?

  2. If my ex calls you and tells you about how close we are and I’m still in connection with him, how would you react?

  3. What was that reason that led to the breakup with your ex?

  4. If you meet my best friend whom I used to share everything of my life, what is the first question that you prefer to ask?

  5. Do you have any close female/male friends other than me with whom you share your all?

  6. What would you do if your best friend do not like me?

  7. How is your relation with your family members and siblings?

  8. If you find that your family is not keen about you dating me, what would you do?

  9. How do you feel about my family? Is there anything you feel uncomfortable when around my family?

  10. How would you like your family to be?

Final Thoughts

These questions will help one to understand each other better! May both of you connect at a deeper level to the next stage of a relationship :).

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