99 Questions to Strengthen the Emotional Intimacy of Your Relationship.

Remember those early days of a new relationship, when you’re both staring star struck at each other across the restaurant table and dreamily fantasizing and talking together about your similarities, goals, and visions for your life? Remember how easy and intuitive it was to ask deep, probing, intimate questions of one another? Remember how close and connected you felt to your honey?

You two were getting to know each other’s internal worlds deeply and that hungry and loving exploration, discovery, and curiosity likely created a strong sense of emotional intimacy between you two, didn’t it?

And yet, if you’re like most long-term couples, over time once the honeymoon phase of your relationship wanes, that same level of newness, curiosity and provocative question-asking of one another can often give way. Instead, many of us slip into end-of-day chats and gripes about work, exchanges about to-do’s and chores, and “what should we do about dinner tonight?” and “what do you want to watch on Netflix” type-dialogue.

Sound familiar?

Now please understand, there’s nothing inherently wrong with this. But often, at least for many couples, I see in my couples counseling practice, this lack of engaging dialogue with one another can sometimes lead to a decline in emotional intimacy and feelings of connection with one another – the very lifeblood and juice of a relationship.

The reality is, getting to know your partner’s internal world is important, not only for the sake of better understanding the person you’re sharing your life with but also because it can lead to a significant increase in your emotional intimacy with one another and a strengthening of your relationship overall.

Indeed, in his extensive research, preeminent couples researcher Dr. John Gottman has found that emotionally intelligent and successful couples are intimately familiar with each other’s worlds. But for most of us in our relationships, over time, this discovery and cultivation of one another’s internal worlds stop being such a high priority.

That’s why I wanted to create a list of 99 questions and conversation starters – in part inspired by my understanding of Dr. Gottman’s concept of Love Maps and also partly inspired by this post, “Save Your Relationships: Ask the Right Questions” of Glennon Melton Doyle of Momastery – to help you and your beloved begin to have some more dynamic, probing conversations to help strengthen and support the emotional intimacy between you.

So read on for a list of 99 questions and conversation starters you can explore with your honey to help strengthen the emotional intimacy of your relationship.

Thinking about starting therapy? Been feeling anxious, depressed or overwhelmed? 

99 Questions to Help Strengthen the Emotional Intimacy of Your Relationship. 

Okay, caveat, in no way am I saying, sit your honey down and plow through this list together. That might be exhausting and likely have the opposite effect of bringing you closer.

What I’m instead inviting you to do is peruse this list, see what strikes your fancy, and then perhaps the next time you and your honey are stuck in traffic or out for a restaurant meal together, call on one of these questions to invite some new, potentially enriching conversation into your relationship.

See what happens when you change the dance steps of your everyday conversation and get deeply curious about that other person across from you, the person you think you know so well but who might have some surprising answers to these questions. See how this impacts the emotional intimacy between you two.

And please, use this list purely as a starting point for generating and brainstorming your own rich and dynamic questions. There are a million things you could ask your honey, and this list of 99 is only meant to be a jumping off point. Sound good? Great. Enjoy the 99 questions.


    1. What do you remember thinking to yourself the first time you saw me?
    2. If our love story was a movie, what movie does it most closely resemble?
    3. What was your favorite date that we ever had? What made it so special for you?
    4. Do you have a favorite adventure that we took together? What made it your favorite?
    5. How and when did you know we’d make it as a couple?
    6. What are three strengths you see between us that we possess as a team?
    7. What’s your very favorite memory of me?
    8. How did you know you wanted to be with me? Did it happen in a moment or over time?
    9. How do I make you feel especially loved in our relationship?
    10. What are some of the little things I do that kind of drive you nuts but also that you secretly like me?
    11. What’s your favorite sexual memory of us? Or top three memories?
    12. Is there anything you’ve been longing for that might spice up our love life?
    13. What’s your favorite non-sexual way of being touched by me?
    14. When was the last time you daydreamed about us and our relationship? What was the daydream about?
    15. What are three strengths or gifts or skills that you think you bring to our relationship?
    16. What character qualities are you most proud of in yourself?
    17. Where do you think you came by those character traits? Do you attribute any of it to your mom or dad?
    18. What’s the biggest lesson your father (or father-figure) ever taught you?
    19. What’s the biggest lesson your mother (or mother-figure) ever taught you?
    20. Is there a smell or a sound that you remember from those early days that still makes you smile?
    21. When you were younger, did you trust your parents?
    22. What was your favorite meal as a kid? Is it still your favorite meal as an adult?
    23. What three adjectives would you use to describe your childhood?
    24. Who was your childhood best friend? What did you guys like to do together?
    25. When you were younger and you got scared or overwhelmed, what would you do to take care of yourself?
    26. Did you have any special or secret spaces you loved to play in as a child?
    27. What was the first album/cd/mp3 you ever bought? Why that one?
    28. What’s your favorite song of all time? Why that one?
    29. If there was a soundtrack of your life, what songs might be on it and why?
    30. Do you ever think about what song you’d like played at your funeral? What do the lyrics of that song mean to you?
    31. When did you know you were in love with me?
    32. What do you think about death? What do you believe happens after we die?
    33. What was your first experience with death? Was it a relative? A pet? How did this impact you?
    34. If you knew you only had a year to live, what would you do in that year?
    35. Who were some of your childhood heroes? The people who made you feel like things were going to be okay and that you were special?
    36. What was your favorite TV show as a kid?
    37. What movie made the biggest impression on you as a teenager? As an adult?
    38. What book made the biggest impression on you as a teenager? As an adult?
    39. If you were stranded on a deserted island, what three books would you take and why?
    40. If you were stranded on a deserted island, what three tools would you take and why?
    41. If you could only eat five foods (plus water) for the rest of your life, what would they be?
    42. If you could make a travel bucket list, what are the top five countries you’re most longing to visit?
    43. If you won the lottery, what would you do with the money? And why?
    44. What are three qualities about me that you were first attracted to?
    45. Is any part of what you would do with your lottery money actually happening in your real life right now? Could it?
    46. What are the qualities you most admire in a man?
    47. What are the qualities you most admire in a woman?
    48. Who, in your opinion, are some real heros?
    49. For what in your life are you most grateful?
    50. If you could be granted three wishes from a genie in a bottle, what would those wishes be?
    51. Is there anything you’ve really longed to do with your life yet that you haven’t?
    52. What do you think is the greatest accomplishment in your life so far? And why?
    53. What do you consider your biggest failure? What did you learn from that failure?
    54. If you could travel back in time to any point in your childhood and give the younger version of you a message, what message would that be and how old would you be?
    55. If you could go back in time to any place and space in the world’s history, what would that be?
    56. What are the biggest stresses that you’re currently facing in your life today? What keeps you up at night that I may not know about?
    57. Who can you count on these days as a real source of support for you?
    58. Which of your relatives is your least favorite? And why?
    59. Who are your favorite relatives and why?
    60. What are three of your best memories with your family? What made those memories really stand out to you?
    61. What’s a question you’ve never asked me but you’re longing to?
    62. What are you most afraid of in this world?
    63.  Do you think is the best part of being a human? What do you think is the hardest part of being a human?
    64. What do you think is the best part of being an adult? And the hardest part?
    65. If you could live in only one outfit for the rest of your life, what would that outfit be?
    66. Are there areas of our relationship that have felt especially challenging lately but that you really feel hopeful about, too?
    67. What new traditions or rituals are you excited about creating our relationship or with the family we create?
    68. What are three of your happiest memories of our early days together?
    69. What are some of the hobbies and routines that bring you joy in your life?
    70. If you had more spare time and no extra responsibilities, how would you spend that spare time?
    71. What three words would you use to describe us as a couple?
    72. If you could have a dinner party with anyone in the world as a guest, who would those guests be?
    73. If you were to describe a perfect day, what would that be for you? A perfect week? A perfect month?
    74. Is there a superhero or fictional character you really identify with? Who is it and why?
    75. What qualities do you really look for in a friendship?
    76. Where do you feel most at peace and ease in the world?
    77. If you could go back to school and study anything you wanted, what would that be?
    78. If your movie was a genre, what genre would it be? What happens next in the movie?
    79. When and what are the moments when you feel most connected to yourself and your soul?
    80. When and what are the moments when you feel our souls connecting the most?
    81. What’s the best compliment you’ve ever received? What’s the best compliment you’ve ever given someone?
    82. What were your secret hopes, fantasies, and wishes for a romantic partnership when you were younger? How about now as an adult? Have they changed?
    83. What’s the best part of our relationship together?
    84. What did your parents teach you about love and relationship?
    85. Who are great models of loving relationships for you?
    86. What are some of your first thoughts in the morning and your last thoughts at night?
    87. How do you see us being different? How do you see us being similar?
    88. What’s your least favorite household chore? What’s your favorite?
    89. Is there any way you’d like for us a couple to give back to others or to our community that we’re not currently doing?
    90. If we as a couple had a theme song, what would it be?
    91. What about the world right now really angers, frustrates, and upsets you?
    92. What moves you and restores your faith in humanity?
    93. Who are the role models and mentors you look up to in life? They can be real people or people you’ve only ever heard of.
    94. What three qualities would you most like to raise your children to embody?
    95. What’s one thing you did in this past week that you’re proud of?
    96. When you’re sad and scared and hurting, how can I best help you in those moments? What do you want me to know in those times?
    97. Tell me more about the person you’re striving to be.
    98. If you could design a perfect day for us, what would that be?
    99. What do you think will help keep our relationship and connection to each strong?

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