The Very Best 200 Deep Questions to Ask

The Very Best 200 Deep Questions to Ask

So you think you know almost everything you can about a person, but you’d still like to dig deeper? Or perhaps you’re only just getting to know someone, but you’re wanting some stimulating and challenging questions to really get to the bottom of who they are? Asking another person tough, personal and profound questions is the best way to truly discover what lies beneath their surface, and to develop a sense of trust between you both. Besides, it can be a super fun experience discovering a side to someone you might never have seen before!

Up for the challenge? Here are 200 of the best deep questions to ask someone!


When was the last time you . . .

— Deep questions to ask

Felt out of control of your emotions?

Had a conversation with a stranger, and what did you talk about?

Had a dream which terrified you?

Stayed up past midnight, and why?

Told someone a secret which you’ve never told anybody?

Felt the universe was trying to guide you?

Wanted to change your career?

Watched a movie that made you cry, and why?

Tried something you had never done before?

Asked for a favour you were afraid to ask for?

Felt uncontrollably happy?

Tried to go out of your way to help someone else?

Listened to bad advice, and what was it?

Felt so embarrassed you wanted to disappear?

Broke someone’s heart, and how?

Stepped into an opportunity without thinking twice?

Believed something that wasn’t true?

Told a lie to get out of a difficult situation?

Suffered from imposter syndrome?

Pretended you thought/felt something that you didn’t?


All about their past

Deep questions to ask

What was your relationship with your parents growing up?

What has been the best phase in your life so far?

How did you feel about school?

What was the most awesome vacation you’ve been on?

Who was your first ever crush?

What is the biggest opportunity you have given up?

How long was your longest relationship?

What was the most rebellious decision you made growing up?

How have you changed most significantly since your childhood?

What was your scariest ever experience?

What’s the craziest thing your previous relationship taught you?

What did you dream of becoming when you grew up?

What were some of your family traditions?

Who did you most admire when you were young and why?

What’s the silliest thing you’ve ever done for love?

What was your biggest fear as a child which is still something you fear today?

What’s the weirdest thing you did on a date?

What are three words you would use to describe your childhood self?

What is your earliest ever memory?

How comfortable do you feel talking about your past?

Next: 100 Brutally-Honest Questions to Ask Friends: Know Them Deeper!


What-If Scenarios

If you wrote a book about yourself, what would you title it?

If you could appear on a reality tv show, what show would it be?

If there is one dream you could choose to turn into reality, what would it be?

If you could dare the person asking you these questions to do anything right now, what would it be?

If you had to post one of your secrets on social media, what would it be?

If your favourite memory could be something tangible, what would it look like?

If you could choose between heaven with your enemies or hell with your friends, what would you choose?

If you could swap your siblings for other people, who would you swap them for?

If you could change one experience in your life, what would it be?

If you could tell your past self anything, what would you say?

If you could get married anywhere in the world, where would it be?

If you could find out the date of your death, would you want to know?

If there was one part of your body you could choose not to age, what would it be?

If someone other than yourself could see your future, who would you want it to be?

If you could only tell one joke for the rest of your life, what would it be?

If you could be a wizard or a genie, which would you be?

If you could grant someone else’s wishes, who would you like it to be?

If you had a crystal ball, what would you ask it to show you?

If you could change your eye colour, would you?

If you could choose to live in one season for the rest of your life, which one would you choose?


All things love

Deep questions to ask

How did you feel saying ‘I love you’ and meaning it for the first time?

What is the biggest dealbreaker for you in a relationship?

How do you feel about letting your partner have full access to your phone?

When do you know you’re in love?

How do you know when you’ve found the one?

What bad habits would you be willing to give up for a relationship?

Kiss on the first date?

Is there such a thing as soul mates?

Have you ever doubted you’ll find your forever love?

Where was the weirdest place you made love?

What is your biggest fear about a relationship?

How would you spend a date if you could only use $30?

Are you confrontational in relationships?

Do you have a movie-worthy kiss memory?

Would you date your ex again?

How do you feel about dating someone who is still close with their ex?

Have you ever regretted leaving a relationship?

What’s your biggest non-physical turn on?

Do you think there has to be a sacrifice in true love?

How old were you when you first experienced romantic love?


Question them on their future

Deep questions to ask

What is the biggest thing you want to achieve in your life?

Where do you want to be 10 years from now?

What’s one thing you look forward to about getting old?

Where is one place you want to take someone else, where would it be, and who would you take?

Do you believe in fortune tellers?

If you could know one thing about your future now, what would it be?

Is there anything that scares you about the future?

Have you ever predicted something significant about your future that came true?

Would you prefer to retain a young body, or a young mind, until you die?

What is an awesome invention you think will be created in your lifetime?

Do you think we can change our future, or that it is already predestined?

What is one thing you want your future self to remember?

What is one experience that you want to relive when you’re older?

What are three things you want to improve on in the next 5 years?

What would be the first holiday you would go on after retiring?

What changes would you be willing to make in your life now if it meant you could retire 10 years early?

What are three new habits you’d like to develop this year?

When you hear the word future, what do you first think of?

Who do you most hope to meet in your future?

Describe what you want your future to be in three words?

Next: 100+ How Well Do You Know Me Questions (Couples & Friends)


Personal beliefs

Deep questions to ask

What does spirituality mean to you?

What do you think about the concept of fate?

Are you guided more by a set of beliefs, or by gut feeling?

What are your thoughts on natural/holistic therapies?

Do you, or have you ever practiced, an unconventional religion?

If you could choose one philosophy to guide the rest of your life, what would it be?

What are three things you truly love about yourself?

Have you ever considered that the world could be flat?

What’s one opinion you have completely changed throughout your lifetime?

Do you have a conviction about what comes after death?

Have you ever been too afraid to speak the truth?

Do you believe in astrology?

What gives you the feeling of meaning in your life?

What is one belief you would never compromise on?

Do you think the Matrix could be real?

What are your thoughts on forgiveness?

Does everyone deserve a second chance?

Is there a God/divine power? And why do you believe there is/isn’t?

Would you accept eternal life if you were granted it?

What is your biggest motivation in life?

Suggested: 110 Hypothetical Questions  // 101 Philosophical Questions // 100 Unanswerable Questions // 120 What If Questions // 101 Thought Provoking Questions


All about their career

Deep questions to ask

Have you ever desperately wanted to change careers, and what to?

Do you derive your identity from your occupation? Be honest

Imagine you could create a career that doesn’t exist yet – what would it be?

How would your 12-year-old self feel about what you currently do for work?

Have you ever had a monster boss?

Would you date your boss?

What would your side hustle be and why?

What did your first job teach you about work?

How have you developed in your most recent job?

Do you feel work has added to or subtracted from your life?

What are the top three qualities you respect in a boss?

Have you ever identified as a workaholic, and how extreme?

What is the bravest thing you’ve had to do in your career to date?

Does your personality change when you’re at work?

How deeply do you trust your work colleagues?

Have there ever been any circumstances at work when you’ve felt undervalued?

What’s the silliest job you’d like to try?

How much does it take for you to take a sick day?

Are you truly content with your salary?

Would you consider your colleagues friends or acquaintances?



What sleeping position do you always revert to?

What’s one name you would never call your kid and why?

Is there a fictional character that you think is exactly like you?

What is the stupidest thing you’ve always wanted to do?

What quote would you get framed for your bedroom wall?

Who is one person you wish you’d never met and why?

What’s the dirtiest thing you’ve ever done?

What is the most money you’d give to a charity in one go?

How many times have you had sex in one day?

What’s the worst argument you’ve ever had with someone?

What’s one juicy secret about someone else you’ve never said out loud before?

What is the best cure for a bad day?

Do you ever question your own sanity?

Have you ever tried meditation, and if so, how do you meditate?

What is one joke that never fails to make you laugh?

What is your one guilty pleasure that no one would expect?

What would you want your legacy to be?

What is the most elaborate way you would propose to someone?

Are you afraid of something unusual?

What is your go-to dinner place?

Next: How Well Do You Know Your Partner? Find out with this Couples Quiz


Would you rather . . .

Delete all social media or move cities?

Take your dream job with a terrible wage, or become a millionaire but hate your job?

Go on a year-long holiday by yourself, or go for the best ever holiday with friends for only one week every year?

Know the way you die or the date of your death?

Learn to speak another language or learn sign language?

Permanently change your hair or permanently change your facial shape?

Lose your driver’s license for 2 years or lose at every game you play for 2 years?

Be the star in your own movie, or play an extra with your favourite celebrity in the lead role?

Live on a tropical island, or live amongst a wood forest?

Discover you were adopted or find out your family belongs to a secret cult?

Have access to your partner’s search history or have unlimited access to their credit card?

Become a famous personality or live in an isolated place?

Date two people at once or date no one?

Be forced to answer 200 personal questions or do stand up comedy in front of a full audience?

Go out to dinner every night or go out to the movies every night?

Have your partner know everything you think, or your mum?

Give up your religion or give up your freedom?

Be able to only say ‘yes’ or only say ‘no’?

Change someone else’s future, or change your past?

Fall in love with someone you can’t have or fall down a flight of stairs?


Media, arts and books

Deep questions to ask

What is one song you can’t live without?

Imagine you could have an artwork painted just for you, what would it be?

When was the last time a song made you cry, and why?

How many movies have you ever watched in one go?

What would be the first line of lyrics to a song about you?

What is the most expensive place you’ve ever eaten?

What does your ideal three-course meal look like?

How easily could you ditch your phone for a day?

How long do you really spend on social media every day?

What songs would you put on a playlist for a first date?

What’s your favourite song to get dancing to?

What was the last book you read and why did you read it?

If you could write a journal entry right now, how would it start?

What is something you don’t like to see in movies?

Why is your favourite artist your favourite?

Who would you ask to write a biography on your life?

Approximately how many books do you own?

What brand would you happily appear in an advertisement for?

Which social media platform do you use the most and why?

What would you like to go viral on youtube for?


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154 Funny Questions to Ask // 154 Weird Questions To Ask // 118 Random Questions To Ask
100 Stupid Questions to Ask // 100 Dumb Questions to Ask

Susannah Twine
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Susannah Twine
Latest posts by Susannah Twine (see all)