Flirty Banter Is Great, But These Questions Will Strengthen Your And Your S.O.'s Bond

Sure, it's fun and flirty to swap solid banter with your new significant other, outwit each other, and toss back and forth excellently executed compliments. But it's also important to sit down and make the time for some intense questions. Take a deep dive into each other’s souls and get into it.

When you first start dating, questions and conversations help you to explore if you're a good match. As the relationship progresses, understanding what the other person needs to take care of their mind and body, supporting their dreams, and knowing what makes them feel fulfilled and joyful can keep the connection strong.

“Relationships, like our bodies, need maintenance," says Carol Bruess, PhD, a professor at the University of St. Thomas and a relationship social scientist. "Making time for deep conversations, ones during which we prioritize fully hearing and listening with an open mind and heart to another’s stories is a relationship vitamin.”

Conversations like this can also be a good way to experience each other’s energy. Now, when you think of deep questions to ask your S.O., you’re probably thinking they’re going to unload all of their trauma. But it isn’t your responsibility to carry that pain and it is better to focus on what brings the other joy rather than what has brought each other pain in the past, says Katya Burdo, PhD, a clinical psychologist based in Boston.

Meet the Experts:
Carol Bruess, PhD is a relationship social scientist and professor emerita of journalism at the University of St. Thomas in Minnesota.

Katya Burdo, PhD is a clinical psychologist based in Boston.

Jocelyn Charnas, PhD is a clinical psychologist based in New York City.

Juanita Guerra, PhD is a clinical psychologist and hypnotherapist based in New York City.

Marisa T. Cohen, PhD, LMFT is a therapist and relationship researcher at Hily app.

No matter what you talk about, spending intentional time actively listening to and speaking to your partner with the utmost vulnerability will build your bond.

"Relationships are created, sustained, changed, and nourished through conversations," Bruess says. "Intentionally giving others our attention, the kind where our entire body, mind, soul is fully present, where we are radically listening to another, soaking in whatever they are saying, expressing, sharing, or even what they are not saying—is one of the most intimate, nourishing acts in a relationship."

How To Make Time For Deep Conversations

Try to routinely set aside time so that you can prioritize these deep conversations. Bruess recommends aiming for these talks once a week.

“A couple can create a simple daily or weekly ritual for nourishing their connection: declaring Sunday morning coffee as 15 minutes of conversation time during which they share two things from the past week that they appreciated about the other, and one thing they need from each other in the week ahead,” says Bruess. Coffee and a nice convo are a perfect way to start the week and a great step toward committing to each other. “Relationships are daily choices,” Bruess adds.

Ahead, find a list of questions to get those deep convos flowing.

Questions About Happiness

Knowing when your partner feels happiest can help you better understand them. And when both of you know when the other feels most free and fulfilled, it's easier to encourage the conditions that foster joy.

  1. When do you feel most free?

  2. When do you feel most joyful?

  3. When do you feel most fulfilled?

  4. When do you feel at peace?

  5. Where is your safe space?

  6. What aspects of your work make you feel these ways?

  7. What aspects of spending time with others make you feel these ways?

  8. What aspects of spending time with me make you feel these ways?

  9. What about your favorite hobby makes you feel happy and fulfilled?

  10. What's one of your happiest childhood memories?

  11. What brought you happiness as a child?

  12. What brought you happiness in your teenage years?

  13. What are some places that make you feel relaxed and calm?

  14. When was a time you felt truly appreciated by a friend?

  15. When was a time you felt truly appreciated by a boss or coworker?

  16. What kinds of activities bring you joy?

  17. If you could go on a day trip anywhere, where would it be?

  18. What would your perfect day look like?

  19. What would you perfect night look like?

  20. Who are some of your friends who bring you true happiness, and how do they do it?

  21. What could I do to make you feel truly, fully happy?

  22. What makes you feel gratitude?

  23. What's something you like about yourself?

  24. What are some qualities you love in your friends and family?

  25. What's a movie or book that always brings you joy?

  26. What music or film genres bring you joy?

  27. How do you find comfort and relief on bad days?

  28. When in your life were you the happiest?

  29. Do you feel more fulfilled when you're around others, or spending time alone?

  30. What makes you laugh?

  31. What helps you feel grounded?

  32. What helps you feel more "you"?

Questions About Dreams

These kinds of questions are helpful for managing expectations, says Jocelyn Charnas, PhD, a clinical psychologist in private practice in Manhattan. “You’d be surprised how often I sit in my office with a new couple, and they haven’t done a lot of communication on very specific things in terms of where they want to live and even if they want to have children,” she says.

Even if your partner’s ideal situation isn’t totally realistic or likely to happen, it can get you to talk about your own perfect scenario and how these two match up, she says. Keep in mind, though, that “they don’t necessarily have to be aligned, one to one,” Charnas says.

Plus, supporting each other's dreams, no matter how unrealistic and improbable they may be, is imperative in connecting with your partner. Expressing your dreams with each other will help both of you reach alignment within yourself and find fulfillment and joy.

  1. Where should our next trip be?

  2. If money weren't a concern, what kind of house or apartment would you love to buy?

  3. How would you like to decorate your dream home?

  4. Would you prefer to live all around the world, or stay in one place?

  5. Where do you really want to live?

  6. If you could move anywhere for just a few years, where would it be?

  7. What has excited you recently?

  8. What would your ideal vacation look like?

  9. What does your ideal life look like?

  10. What hobby do you wish you could pursue?

  11. What's your dream job?

  12. What was your dream job as a child?

  13. What are some of your biggest professional goals?

  14. What are some of your biggest goals, outside of work?

  15. How do you define success?

  16. What do you imagine our life together looks like in the future?

  17. What would you do for a year if you were free to do whatever you wanted?

  18. What kind of job would you work, if money weren't a concern?

  19. Are there any skills you'd like to learn someday?

  20. Is there anywhere you want to visit before you die?

  21. Is there anything you hope to achieve in your lifetime?

  22. If you could be the best in the world at anything, what would it be?

  23. Would you like to be famous for anything?

  24. Are you interested in having pets?

  25. Are you interested in having kids?

  26. If you're interested in having kids, how would you like to raise them?

  27. Do you dream of getting married one day?

  28. What would your dream wedding proposal look like?

  29. What would you dream wedding be like?

  30. What would you dream honeymoon be like?

  31. Would you ever want to go back to school?

  32. If you could take any kind of class, what would it be?

  33. If you could start your own business, what would it be?

  34. If you didn't have to work, how would you spend your days?

  35. If you could be skilled at any art form, what would it be?

  36. How can I help you accomplish your goals?

  37. Would you say you're living your dream life?

  38. Have you ever had to give up on a dream?

  39. Would you describe yourself as ambitious?

  40. If you came upon a lot of money, what would you do with it?

  41. What's on your bucket list?

  42. Do you have any ten-year goals?

  43. What's something you've always wanted to do, and haven't been able to?

Questions About Self-Care

Valuing self-care is the greatest way to prepare yourself for intimacy—and for creating a deeper bond with your S.O., says Burdo. It's important to understand what your partner needs to take care of themselves, and how much time and space they need alone.

“It tells you what they like and what makes them feel good," says licensed clinical psychologist Juanita Guerra, PhD. This can also help you see what’s most important to them—and that’s info you can mine in the future when it comes to treating them well.

  1. What is the best way for me to tell you that I am out of balance?

  2. How are you most comfortable letting me know that you are out of balance?

  3. What do you do to take care of yourself?

  4. How much space/time do you need for yourself?

  5. How can I support you in taking care of yourself?

  6. When you are out of balance, what do you need from me?

  7. What does your perfect day off look like?

  8. How can I be more supportive of you in day-to-day life?

  9. What kind of music calms you down?

  10. What kind of exercise makes you feel good?

  11. Are there any hobbies that soothe you?

  12. What helps you get a good night's sleep?

  13. Would you say you're good at taking care of yourself?

  14. How do you recharge?

  15. How do you like to be cared for when you're sick?

  16. How do you like to be cared for when you're sad?

  17. How do you typically cope with grief or loss?

  18. What coping mechanisms work for you on bad mental health days?

  19. What helps you when you feel stressed or overwhelmed?

  20. What helped you get through the hardest time of your life?

  21. Who was there for you at your lowest moments?

  22. Do you think you're good at asking for help?

  23. How do you like to show up for your friends?

  24. How do you like your friends to show up for you?

  25. What are your experiences with therapy?

  26. Who is in your support system?

  27. How can I support you through tough times?

  28. How would you define self-care?

  29. What are some mantras that have stuck with you?

  30. Who inspires you?

  31. What inspires you?

Questions About Your Relationship

Never underestimate the power of a relationship check-in. Whether you have them once a month or once a year, there's always something to learn from your partner as your relationship evolves. "In relationships, we always make assumptions based on what we think and have experienced before. Having regular check-ins with your partner will greatly improve your understanding of your partner’s perspectives and perceptions that affect your relationship," says Marisa T. Cohen, PhD, LMFT, a relationship researcher at the Hily app.

Think of it as a way of getting in front of any potential miscommunications or problems before they arise. "It’s best to be proactive, not just react to problems that are already there," adds Cohen.

  1. What in this relationship has been hard for you to deal with?

  2. What are some challenges we've been able to overcome together?

  3. What do you wish there was more of in our relationship?

  4. Is there anything you miss from the earlier days of our relationship?

  5. What’s your favorite date that we’ve been on?

  6. What's the best trip we've taken together?

  7. What kinds of dates should we do more often?

  8. What is your favorite thing to discuss with me?

  9. Is there anything you wish we discussed more?

  10. What are some topics you feel uncomfortable discussing with me?

  11. What has been your favorite memory from our time together so far?

  12. What's a shared memory of ours that makes you laugh?

  13. What's your favorite gift that I've given you?

  14. What's the most romantic thing I've ever said to you?

  15. What's the most romantic thing I've ever done for you?

  16. What do you think is the most romantic thing you've ever done in our relationship?

  17. What quality about our partnership do you enjoy the most?

  18. What do you like the most about my personality?

  19. Is there anything about me that gets on your nerves?

  20. Is there anything in our relationship that makes you feel insecure?

  21. What is something you look forward to in our relationship?

  22. What are some songs that remind you of me?

  23. How do I make you feel about yourself?

  24. What do you think we have in common?

  25. Do you think we share the same values?

  26. Do you think we share the same love languages?

  27. What do I do that makes you feel loved?

  28. How can I make you feel even more loved?

  29. How can I make you feel appreciated and loved after a fight?

  30. Do you think we're good at apologizing after arguments?

  31. Do you think we have compatible communication styles?

  32. How do you describe me to a stranger?

  33. How do you speak about me to your family and friends?

  34. Where do you see our relationship headed?

  35. What's something I've taught you?

  36. What's something new you learned about me recently?

  37. Do you feel like you're still learning new things about me, or do you know it all?

  38. What's something that surprised you about me once we started getting more serious?

  39. How do you define a loving relationship?

  40. How do you define commitment?

  41. What do you remember about the first time we met?

  42. What was your first impression of me?

  43. When did you first realize how you felt about me?

  44. If you could change anything about our relationship, what would it be?

  45. Has trust ever been an issue in our relationship?

  46. Do you ever get jealous in our relationship?

  47. How can I make you feel more secure in our relationship?

  48. How has our relationship grown stronger over the months (or years)?

  49. What would our relationship look like if we lived together, or took things to the next level?

  50. Are there any concerns you have about our future together?

Questions About Sex

Sex is undoubtedly an important part of a relationship. This includes how often you like to have sex, the kind of sex you like to have, and how you define sex in general. If you already have a good sense that the two of you are sexually compatible, you can ask more specific questions.

And yes, you should set up a time to talk about sex. "The best time to have a discussion about sex is when both partners agree that they are able to," says Cohen. "The conversation requires vulnerability, so it’s important that it's not rushed or done at a time when a person’s attention is divided." In other words, talking to your partner about the new advanced-level sex position you want to try should not happen while they're washing the dishes. You also don't want to wait until things are getting hot and heavy to talk about it, either.

  1. What does desire mean to you?

  2. What does pleasure mean to you?

  3. How would you define great sex?

  4. What turns you on?

  5. What turns you off?

  6. Where do you like to be kissed?

  7. Where do you like to be touched?

  8. What are your sexual boundaries?

  9. What do you remember about our first time having sex?

  10. What's something I do that always turns you on?

  11. What kinds of sex toys do you like to use in the bedroom?

  12. Is there a type of sex toy you've always wanted to buy?

  13. What's your favorite part of having sex with me?

  14. What's the best orgasm you've ever had?

  15. What's the hottest thing I've ever said to you?

  16. What's the hottest thing I've ever worn before or during sex?

  17. Do you have sex dreams frequently? Tell me about them.

  18. What's the most recent sex dream you've had about me?

  19. How has your relationship with sex and intimacy changed over time?

  20. How would you describe the feeling of having an orgasm?

  21. How can I make you feel appreciated and wanted in bed?

  22. Do you like public sex?

  23. Do you like it when I tease you in bed?

  24. Would you ever be interested in a threesome? If so, who would be your dream third partner?

  25. Which fantasies are you interested in enacting?

  26. What kinds of kinks do you feel ambivalent about?

  27. What kind of kinks are a hard no for you?

  28. Is there a kink or fetish you'd like to try?

  29. What are your favorite sex positions?

  30. What's a sex position you'd like to try?

  31. Do you wish we mixed up our sex positions more often?

  32. What do you think about when you masturbate?

  33. Do you enjoy porn or erotica? If so, what types?

  34. What do you enjoy doing the most during sex, and why?

  35. What kind of dirty talk do you enjoy?

  36. What kind of sexting do you enjoy?

  37. How can we keep our sex life exciting?

  38. How do you think our sex life has evolved over the months or years?

  39. How would you define sexual compatibility?

  40. Do you think we're sexually compatible?

  41. How important is sex in a relationship?

  42. How often do you like to have sex in a relationship?

  43. Would you prefer it if we had sex more or less frequently?

  44. Would you rather have sex more often, or try more new things?

  45. What's one of your sexiest memories of me?

  46. When was a time I turned you on in public?

  47. What do you like doing after sex?

  48. What time of day do you like to have sex?

  49. Besides the bedroom, where do you like to have sex?

  50. If you could have sex anywhere, where would it be?

  51. When it comes to sex, do you prefer anticipation or spontaneity?

Questions About Past Relationships

It goes without saying that your past can influence your present, which is why talking to your partner about past relationship(s) is a no-brainer. Triggers, frustrations, and other feelings can bleed from one relationship into the next. Talking with your partner about their experiences—and yours—can give you insight into each other and your expectations.

That said, past relationships can be a touchy subject, so keeping things open and honest will make a world of difference. "The basic rule is to discuss all the questions that influence your connection and affect your lives as individuals," says Cohen. "Don’t bottle up your feelings. Be open and genuinely interested in exploring your partner’s life." And if strong emotions come up while talking through it all, approaching them with curiosity and trying to source where they stem from can benefit the conversation.

  1. What in past relationships has been hard for you to deal with?

  2. What kinds of crushes did you have growing up?

  3. Who was the first person you ever really liked?

  4. What was your first kiss like?

  5. What was your first sexual experience like?

  6. What was the worst date you've ever been on?

  7. What kind of relationship did you have with dating apps?

  8. How would you describe your "type"?

  9. Have you been in love before?

  10. What was your first heartbreak like?

  11. What was your worst heartbreak like?

  12. What did you learn from your experiences with heartbreak?

  13. In the past, when have you known that a relationship was over?

  14. In the past, were you more interested in relationships or casual situations?

  15. Do you have any regrets from your last relationship?

  16. What have you learned about love from past relationships?

  17. Are you still friends with any of your exes?

  18. How has your view of relationships and love changed over time?

  19. What is the most valuable thing you have learned about yourself as a partner from your relationship experiences?

  20. What experiences from past relationships still weigh on you, and what are some ways I can support you?

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