42 Best Deep Questions To Ask Your Boyfriend

This post is all about deep questions 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!

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

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

BEST DEEP QUESTIONS TO ASK YOUR BOYFRIEND: OUR RELATIONSHIP

What did you think of me when we first met?
What makes you super happy in our relationship?
How long did you think our relationship would last when we first started dating?
Whats your favorite memory of us?
Whats one thing you’re scared to ask me but really want the answer too?
Whats one thing that you wish I did more?
What would be your perfect date night?
What are three key elements in a successful relationship?

Ask these questions next → 105 Questions To Ask Your Crush That Will Actually Start A Conversation

BEST DEEP QUESTIONS TO ASK YOUR BOYFRIEND: FUTURE

If you were told you had a terminal illness, what would be three things you’d want to do?
If you could live to 90 and have either the mind or body of a 30-year-old, what would you choose?
What is a tradition you did with your family that you want to continue on with your kids?
How do you picture your life when you’re 60?
Would you surprise me with an expensive gift, or would you consult me before spending the money on it?
Do you think a proposal should be a grand public display or a private intimate moment?
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: PERSONAL

What is something you did that you have regretted?
Where do you see yourself in five years?
What are some things in life you had to learn the hard way?
If you could go back in time to give advice to your younger self, what would you say?

Ask these questions next → 100 Funny Questions To Ask A Guy

BEST DEEP QUESTIONS TO ASK YOUR BOYFRIEND: TOUCHY SUBJECTS

Why do you think the divorce rate is so high these days? Couples who have decided to end their marriage should learn which questions to ask a divorce lawyer to ensure they are both prepared for the whole process.
What do you think is the biggest flaw of the welfare system?
If you were running for president, what are three key things you would include in your campaign?
Are you pro-choice or pro-life?
How do you feel about genetically modified food?
What is one thing that you feel would make any small business owner more successful?
What invention do you think has done the most for the human race?
Should children be allowed to have cell phones?
Do you think a person’s outward appearance says anything about who they are as a person?
How important do you think it is to do well in school?
Would you consider yourself proud to live in this country?
Is there anything too serious to be joked about?
What are your views on the political system?
Do you believe in heaven?