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100 Deep Questions to Ask When You Want to Take Your Relationship to the Next Level

Remember the game 20 Questions? Many of us used to play it as kids to pass the time during long car trips. We may be older, but the setup can still be useful in a slightly different way: as a means of getting to know a special person a little better. Deep questions to ask might help take a crush to the next level, strengthen your relationship with your spouse or allow you to turn a casual acquaintance into a close, trusted friend.

Curious about the kinds of deep questions to ask the people in your life? We’ve got you covered with a range of ideas, from lighthearted conversation starters to more serious, thoughtful probes. To truly strengthen your relationship, don’t speed through the questions—take your time and ask follow-ups. Remember, this is a jumping-off point for a discussion, not an interview.

So the next time you’re spending some quiet moments with a boyfriend, girlfriend, partner or pal, use these deep questions to ask the stuff that’ll get them talking and bring you closer. You just might learn something surprising!

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Deep questions to ask your boyfriend

  • What is the funniest thing that’s ever happened to you?
  • If you won the lottery, would you quit your job or keep working?
  • How do you build friendships with other guys?
  • Do you believe in soulmates?
  • What is your idea of the perfect date?
  • How do you like to spend a rainy weekend?
  • Are you a spender or a saver?
  • What is your biggest fear?
  • What is your worst habit?
  • Do you believe in aliens? Convince me you’re right.
  • Could you live off the grid?
  • What do you like best about your job?
  • What scares you the most about being in a relationship?
  • What do you think is your best feature?
  • Do you want to have kids?
  • What’s your ideal vacation?
  • Do you think people can change?
  • What wakes you up in the middle of the night?
  • If you could have one superpower, what would it be?
  • What is your favorite movie and why?

Deep questions to ask your girlfriend

  • What are you most proud of?
  • Do you believe in love at first sight?
  • If you could ask a time traveler one question about the future, what would it be?
  • Where do you see yourself in five years?
  • What is your love language?
  • Do you vote?
  • What are your relationship goals?
  • What do you want your legacy to be?
  • When do you feel most alone?
  • What is your favorite memory?
  • What is your dream job?
  • What gives you a sense of peace or inner calm?
  • If you could go back in time, what moment would you choose?
  • What is the worst gift you’ve ever received?
  • What is your silent act of defiance?
  • Do you believe in an afterlife?
  • What motivates you when you need a boost?
  • How do you define success?
  • What role does love play in your day?
  • Is social media good or bad for society?

Deep questions to ask your partner

  • What’s your favorite memory from childhood?
  • How would you describe the perfect day?
  • How often do you think about death?
  • What is your biggest regret?
  • How do you define work-life balance?
  • Can men and women ever be equal?
  • Which country do you want to visit next, and why?
  • What did a past relationship teach you?
  • Are you still friends with anyone from high school?
  • What is your biggest guilty pleasure?
  • What’s the craziest thing you’ve ever done for someone?
  • Which parent are you closest to?
  • How do you react when you’re upset?
  • What are you most thankful for?
  • What impresses you?
  • What is something I don’t already know about you?
  • What was the worst phase in your life?
  • If you’re in a bad mood, do you want to be cheered up or left alone?
  • Is it important to forgive people?
  • Do you judge a book by the cover?

Deep questions to ask your friend

  • If you could live anywhere, where would it be?
  • What’s the best book you’ve ever read and why?
  • What’s the greatest gift you were given?
  • Would you rather live a long, uneventful life or a short, extraordinary life?
  • Who is your hero?
  • Who do you trust completely?
  • Which music makes you the happiest?
  • Do you think you’re a good person?
  • What does “home” feel like to you?
  • Where is your favorite place in the world, and why?
  • Do you believe in karma?
  • What’s your biggest regret?
  • What takes your breath away?
  • What’s the toughest aspect of your job?
  • If you could change one thing about yourself, what would it be?
  • What quality do you value most in a friend?
  • Who was your idol growing up?
  • How do your friends describe you?
  • What’s your biggest pet peeve?
  • Do you consider yourself brave?

Deep questions to ask anyone you want to know better

  • Can you tell me about your happiest moment?
  • What do you think about when you’re falling asleep?
  • What role does religion play in your life?
  • What, if anything, do you find unforgivable?
  • Are you afraid to die?
  • What’s your most prized possession?
  • What’s something you used to believe strongly but no longer do?
  • What defines your identity?
  • If you were king or queen for the day, what would be your first decree?
  • When was the last time you cried?
  • If you could redo a single year of your life, which would you choose?
  • If given the chance, would you live on Mars?
  • What scares you the most about the future?
  • How do you deal with conflict?
  • What makes you feel vulnerable?
  • What’s your favorite way to relax?
  • Are you good with finances?
  • Is art important, and why do you believe that?
  • What was the most intense experience of your life?
  • Do you believe in fate?

Why trust us

For over 100 years, Reader’s Digest has explored the nuances of relationships, working with such luminaries as Dr. Ruth Westheimer, John Gottman, PhD, and Leo Buscaglia (“Dr. Love”). We ran a decade-long relationships column and have published a compendium of features, Love and Marriage: The Reader’s Digest Guide to Intimate Relationships. We support this information with credentialed experts and primary sources such as government and professional organizations, peer-reviewed journals and our writers’ personal experiences where it enhances the topic. We verify all facts and data and revisit them over time to ensure they remain accurate and up to date. Read more about our team, our contributors and our editorial policies.

Expert Tips for Making Small Talk

Flirty Questions to Ask a Girl

How to Avoid Awkward Silence

The post 100 Deep Questions to Ask When You Want to Take Your Relationship to the Next Level appeared first on Reader's Digest.



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