42 Best Deep Questions To Ask Your Boyfriend

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This post is all about deep questions to ask your boyfriend.

best deep questions you need to ask your boyfriend

Confession: My boyfriend and I are really bad at going to restaurants and going on our phones.

I know, it's bad. We (I haha) are REALLY working on it. Last time I was visiting him (we're long distance) I ended up searching Pinterest for some really good questions that could spark interesting conversations.

Now, we've been dating for almost four years. We are really open with each other and I feel like there is nothing that hasn't been discussed. {READ: 5 Must-Know Ways To Make Sure Your Long Distance Relationship Lasts}

When searching this, I wasn't really sure I would find questions that would be interesting enough but surprisingly, I found really great ones that led to conversations that lasted all night!

This post shows you the best deep questions to ask your boyfriend.

WARNING: These questions aren't all exactly PG (what fun would that be;).

Best Deep Questions To Ask Your Boyfriend: Our Relationship
  1. What did you think of me when we first met?
  2. What makes you super happy in our relationship?
  3. How long did you think our relationship would last when we first started dating?
  4. Whats your favorite memory of us?
  5. Whats one thing you're scared to ask me but really want the answer too?
  6. Whats one thing that you wish I did more?
  7. What would be your perfect date night?
  8. What are three key elements in a successful relationship?
Best Deep Questions To Ask Your Boyfriend: Future
  1. If you were told you had a terminal illness, what would be three things you'd want to do?
  2. If you could live to 90 and have either the mind or body of a 30-year-old, what would you choose?
  3. What is a tradition you did with your family that you want to continue on with your kids?
  4. How do you picture your life when you're 60?
  5. Would you surprise me with an expensive gift, or would you consult me before spending the money on it?
  6. Do you think a proposal should be a grand public display or a private intimate moment?
  7. If we had children, what features would you want them to get from you and which from me?
Best Deep Questions To Ask Your Boyfriend: Past Questions
  1. What is something you did that you have regretted?
  2. Where do you see yourself in five years?
  3. What is some things in life you had to learn the hard way?
  4. If you could go back in time to give advice to your younger self, what would you say?

{RELATED: 31 Budget-Friendly Date Ideas You Need To Try}

Best Deep Questions To Ask Your Boyfriend: Possible Touchy Questions
  1. Why do you think the divorce rate is so high these days?
  2. What do you think is the biggest flaw of the welfare system?
  3. If you were running for president, what are three key things you would include in your campaign?
  4. Are you pro-choice or pro-life?
  5. How do you feel about genetically modified food?
  6. What is one thing that you feel would make any small business owner more successful?
  7. What invention do you think has done the most for the human race?
  8. Should children be allowed to have cell phones?
  9. Do you think a person’s outward appearance says anything about who they are as a person?
  10. How important do you think it is to do well in school?
  11. Would you consider yourself proud to live in this country?
  12. Is there anything too serious to be joked about?
  13. What are your views on the political system?
  14. Do you believe in heaven?

{These were all taken from Paired Life. I think these are genius questions they came up with!!}

Best Deep Questions To Ask Your Boyfriend: Random
  1. What's one secret you've wanted to know about me, but have never asked?
  2. If you could fix one world problem what would it be?
  3. If you could have chosen your name, what would it be?
  4. Whats your favorite thing about yourself?
  5. If you could change one thing about yourself what would it be?
  6. Whats your biggest insecurity?
  7. How important is it for you to save money or invest?

If you're anything like me, you love seeing how your boyfriend will answer deep questions.

These 42 best deep questions to ask your boyfriend will turn a normal dinner into a night to remember.

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  1. I love these! Me and my long distance boyfriend are the same at dinner. I’ll definitely test this out with him:)

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