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The Best Deep Questions To Ask A Guy (Or A Boyfriend Or Man You Like)

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Use These Deep Questions (To Ask a Guy) and Watch Him Get Serious and Personal With You!
The Best Deep Questions To Ask a Guy (Or a Boyfriend Or Man You Like) post image
If you’re looking for fun, lighthearted conversation topics well … you came to the wrong place. (Go here if you want fun questions to ask.)

If you want to get to know someone on a deep, profound level, then we’ve got exactly what you need.



Most people shy away from the deep stuff and as a result, most connections are surface level and superficial at best. The way to really connect and get to know someone is to go deep.

These questions range from personal to philosophical. Some may bring up painful memories, others are mind-benders that are just interesting to think about.

Just know your audience. If it’s a guy you have a crush on that you don’t know so well, you may want to go with some of the more neutral questions. If it’s someone you connect with deeply, then these questions can help you take it to the next level.

Deep Conversation Starters
These are great questions to ask when you’re getting to know someone.

Do you think all diseases will be cured someday?
What do you think keeps people in toxic relationships?
Do you believe we all have a soul or are we just a series of electrons and neurotransmitters?
What could the government do to actually improve everyone’s lives?
Do you think technology is destroying us or enhancing our lives?
Are you an introvert or extrovert?
What was the happiest period of your life?
What does your perfect day look like?
What 3 qualities do you admire most in another person?
How would your closest friends describe you?
Do you think men and women can ever really be friends?
What has been your favorite age so far?
Do you believe in reincarnation?
What’s one thing you always procrastinate on?
What’s the best way to end a long day?
What do you wish you could remember more clearly?
What is your proudest accomplishment?
What is the biggest sin our of the 7 deadly sins (pride, greed, lust, envy, gluttony, wrath, sloth)?
What is your definition of love?
What should a healthy relationship provide for the people in it?
What is your biggest goal in life?
What is your weirdest habit?
Do you have any phobias?
Do you believe in aliens?
Do you feel fulfilled by your job?

Personal Questions to Ask a Guy
The following questions go a little deeper without going too far.

What is one thing no one realizes about you?
Do you think we will ever have a definitive answer for what is the meaning of life?
What do you think we’re doing here?
What is one behavior you never tolerate?
What song speaks to your soul?
What always makes you angry?
What always makes you cry?
What is one thing you take for granted?
What is one thing you appreciate the most?
Do you believe everything happens for a reason?
Do you believe in destiny?
Are you a religious or spiritual person?
Do you believe in the afterlife?
Do you believe in heaven?
Do you believe in karma?
After you die, what would you like to be remembered for?
What is one thing you can never forgive?
Who can you talk to about anything?
Have you ever had your heart broken?
What is one thing you’re happy you’ll never have to do again?
What was your biggest ‘what was I thinking’ moment?
Have you ever been in trouble with the law?
What is the best compliment you’ve ever received?
How has your sense of right and wrong evolved?
If you woke up tomorrow with no fear, what would you do first?
What makes you feel alive?
What’s one mistake you will never make again?
What would you do differently if you got the chance to relive the past 5 years?
What is one bad habit we are all better off without?
What is the biggest lie people tell themselves?
In what ways are you stronger than you look?
What do people thank you for most often?
What is always worth the wait?
What quote or mantra do you tell yourself most often?
Have you ever questioned your sanity?
Do you have any recurring dreams?
If you could live the rest of your life and never feel pain, would you?
Where does true happiness come from?
Do you get overwhelmed easily?
Have you ever lost someone close to you?
What lesson do you wish you learned earlier in life?
Which aspect of your life is going really well right now, and which area could use some help?
What are you most insecure about?
Do you think people can really change?
How much control do we have over our lives?
What kind of parent do you think you’ll be?

Soul-baring Questions
These questions go as deep as you can go. Proceed with caution as they may hit a raw nerve.

Did you have a happy childhood?
If you could write a note to your younger self, what would you say in 3 words?
What would you change about your childhood?
Have you ever been addicted to something?
What is your biggest fear?
What is the most shameful thing you’ve ever done?
What is your biggest regret in life?
What is one thing you would change if you could go back in time?
Have you ever had a near-death experience?
What keeps you up at night?
Who is one person you aspire to be like?
What did your parents give you that you hope to give your kids?
What is the worst thing you’ve ever done to someone?
What is something you’re really bad at?
What would you do if you woke up tomorrow with no fear?
What is something you’re judgmental about?
What has been the biggest blessing in disguise in your life?
Is there a memory in your life you wish you could erase?
What would you do differently if you knew no one would judge you?
What was the lowest point in your life?
What was your biggest heartbreak in life?
What keeps you going when the going gets tough’?
What gives your life purpose and meaning?
When was the last time you had a good cry?
What trait do you envy in others?
In what area of life do things never seem to go your way?
What do you like most about yourself?
What do you dislike most about yourself?
What has been your biggest life-changing decision?

I hope this article gave you some fresh ideas for deep questions to ask a guy. If your focus is on building a connection with a guy, there are two important moments you need to be aware of. The first is that at some point In your relationship, your man will start to pull away. You may notice him becoming more distant and less engaged. It seems like he’s losing interest in you and you worry that soon he’s going to just leave. Do you know what to do to get things back on track? If not, read this next: If He’s Pulling Away, Do This...

The next issue arises at that inevitable point when the man asks himself: Do I want to commit to this woman for the long term? The answer will determine everything. Do you know what makes a man see a woman as girlfriend/wife material? Do you know what inspires a man to commit? If not, you need to read this too: The #1 Things Men Desire in a Woman

Use These Deep Questions (To Ask a Guy) and Watch Him Get Serious and Personal With You!
If you’re looking for fun, lighthearted conversation topics well … you came to the wrong place. (Go here if you want fun questions to ask.)

If you want to get to know someone on a deep, profound level, then we’ve got exactly what you need.

Most people shy away from the deep stuff and as a result, most connections are surface level and superficial at best. The way to really connect and get to know someone is to go deep.

These questions range from personal to philosophical. Some may bring up painful memories, others are mind-benders that are just interesting to think about.

Just know your audience. If it’s a guy you have a crush on that you don’t know so well, you may want to go with some of the more neutral questions. If it’s someone you connect with deeply, then these questions can help you take it to the next level.

Deep Conversation Starters
These are great questions to ask when you’re getting to know someone.

Do you think all diseases will be cured someday?
What do you think keeps people in toxic relationships?
Do you believe we all have a soul or are we just a series of electrons and neurotransmitters?
What could the government do to actually improve everyone’s lives?
Do you think technology is destroying us or enhancing our lives?
Are you an introvert or extrovert?
What was the happiest period of your life?
What does your perfect day look like?
What 3 qualities do you admire most in another person?
How would your closest friends describe you?
Do you think men and women can ever really be friends?
What has been your favorite age so far?
Do you believe in reincarnation?
What’s one thing you always procrastinate on?
What’s the best way to end a long day?
What do you wish you could remember more clearly?
What is your proudest accomplishment?
What is the biggest sin our of the 7 deadly sins (pride, greed, lust, envy, gluttony, wrath, sloth)?
What is your definition of love?
What should a healthy relationship provide for the people in it?
What is your biggest goal in life?
What is your weirdest habit?
Do you have any phobias?
Do you believe in aliens?
Do you feel fulfilled by your job?
Personal Questions to Ask a Guy
The following questions go a little deeper without going too far.

What is one thing no one realizes about you?
Do you think we will ever have a definitive answer for what is the meaning of life?
What do you think we’re doing here?
What is one behavior you never tolerate?
What song speaks to your soul?
What always makes you angry?
What always makes you cry?
What is one thing you take for granted?
What is one thing you appreciate the most?
Do you believe everything happens for a reason?
Do you believe in destiny?
Are you a religious or spiritual person?
Do you believe in the afterlife?
Do you believe in heaven?
Do you believe in karma?
After you die, what would you like to be remembered for?
What is one thing you can never forgive?
Who can you talk to about anything?
Have you ever had your heart broken?
What is one thing you’re happy you’ll never have to do again?
What was your biggest ‘what was I thinking’ moment?
Have you ever been in trouble with the law?
What is the best compliment you’ve ever received?
How has your sense of right and wrong evolved?
If you woke up tomorrow with no fear, what would you do first?
What makes you feel alive?
What’s one mistake you will never make again?
What would you do differently if you got the chance to relive the past 5 years?
What is one bad habit we are all better off without?
What is the biggest lie people tell themselves?
In what ways are you stronger than you look?
What do people thank you for most often?
What is always worth the wait?
What quote or mantra do you tell yourself most often?
Have you ever questioned your sanity?
Do you have any recurring dreams?
If you could live the rest of your life and never feel pain, would you?
Where does true happiness come from?
Do you get overwhelmed easily?
Have you ever lost someone close to you?
What lesson do you wish you learned earlier in life?
Which aspect of your life is going really well right now, and which area could use some help?
What are you most insecure about?
Do you think people can really change?
How much control do we have over our lives?
What kind of parent do you think you’ll be?
Soul-baring Questions
These questions go as deep as you can go. Proceed with caution as they may hit a raw nerve.

Did you have a happy childhood?
If you could write a note to your younger self, what would you say in 3 words?
What would you change about your childhood?
Have you ever been addicted to something?
What is your biggest fear?
What is the most shameful thing you’ve ever done?
What is your biggest regret in life?
What is one thing you would change if you could go back in time?
Have you ever had a near-death experience?
What keeps you up at night?
Who is one person you aspire to be like?
What did your parents give you that you hope to give your kids?
What is the worst thing you’ve ever done to someone?
What is something you’re really bad at?
What would you do if you woke up tomorrow with no fear?
What is something you’re judgmental about?
What has been the biggest blessing in disguise in your life?
Is there a memory in your life you wish you could erase?
What would you do differently if you knew no one would judge you?
What was the lowest point in your life?
What was your biggest heartbreak in life?
What keeps you going when the going gets tough’?
What gives your life purpose and meaning?
When was the last time you had a good cry?
What trait do you envy in others?
In what area of life do things never seem to go your way?
What do you like most about yourself?
What do you dislike most about yourself?
What has been your biggest life-changing decision?
I hope this article gave you some fresh ideas for deep questions to ask a guy. If your focus is on building a connection with a guy, there are two important moments you need to be aware of. The first is that at some point In your relationship, your man will start to pull away. You may notice him becoming more distant and less engaged. It seems like he’s losing interest in you and you worry that soon he’s going to just leave. Do you know what to do to get things back on track? If not, read this next: If He’s Pulling Away, Do This...

The next issue arises at that inevitable point when the man asks himself: Do I want to commit to this woman for the long term? The answer will determine everything.

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