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Valentine's Day Date Night Conversation starters

Are you doing anything special with someone on Valentine's Day?

A couple's massage maybe? We know how challenging making the time to relax with a loved one can be sometimes.

A fancy lunch date and a movie after?

Or maybe you will be focused on work because unfortunately, this year Valentine's day falls on a Tuesday, which is not the most romantic day of the week.

If you are lucky, you will be off of work that day. Like me, your plans will consist mostly of sleeping, a lengthy self-care routine, a potential shopping spree for sexy lingerie, and perhaps an elaborate home-cooked meal if I can be bothered.

I am going to be all laid up in bed waiting for my husband to come home from work.

Maybe you will be all dressed up and sitting across from your sweetheart at a fancy restaurant. Or maybe you will opt for

the stay-at-home romantic dinner you will have made together. Whatever your Valentine scenario, I would like to help you spark a deeper connection with each other.

You could indulge in the same old casual conversation; how your day was, details about the people in your lives, the things you have to get done. Or... You can take this opportunity to get down and dirty with these questions.


So, are you ready to get started?


Here are a few reminders:

Find your peaceful spot in the house or elsewhere.

Flip a coin to see who will be the first one to answer the first question. Then alternate after that. Read the question and the information below the question out loud. Then ask the question again directly to your partner.

Simply pluck out a few questions that intrigue you most. And begin your love talk.Try not to read ahead to the next questions, but instead focus intently on the question you are asking and answering.

Sit close to each other so you can touch and look at each other face to face.

Give each other plenty of time to respond, and as you are listening to your partner answer a question, try not to think ahead about your own answers. Just be fully present for your partner and practice

  1. What specific behaviors and actions from me feel most loving to you?

  2. How would you like me to verbally express my love?

  3. What kind of physical touch feels the most loving?

  4. What makes you feel more loving toward me?

  5. How can I ask for more love from you?

  6. What might I say or do that would feel unloving to you?

  7. How will I know when you need more love from me?

  8. How often do you need to hear me say, “I love you”?

  9. What does unconditional love mean to you?

  10. How can we rekindle love when we see signs of apathy or distance?

  11. What specific actions and words make you feel respected?

  12. How have you been disrespected in the past, and how did it make you feel?

  13. Am I doing anything now to make you feel disrespected?

  14. Are there any ways in which you feel undeserving of respect?

  15. How can I support you in feeling more respected in this area?

  16. What acts of kindness from me mean the most to you?

  17. How have I unknowingly been less than kind to you?

  18. How should I let you know that I feel you’re being unkind?

  19. Do you see me as a kind person to you and others?

  20. What acts of kindness or service could we perform together that would strengthen our relationship?

  21. How can I best communicate a problem or concern?

  22. Is there anything about my tone of voice that bothers you?

  23. Do you feel completely free to talk with me about anything?

  24. Am I free to talk with you about anything?

  25. What topics do you most enjoy discussing with me?

  26. What could I do to make you feel more seen, heard and understood?

  27. Do you have any negative emotions about our relationship you need to express?

  28. What should I never say to you in anger or playfulness?

  29. Is there anything I do now that crosses your boundaries and makes you uncomfortable?

  30. Is there anything about our sexual intimacy that makes you unhappy or uncomfortable? If so, what?

  31. Do you ever feel uncomfortable saying “no” or speaking up for yourself with me? If so, why?

  32. Where are you unwilling to compromise?

  33. How should we handle it, if a boundary has been crossed?

  34. How often would you like to have sex?

  35. What sexual fantasies do you have that we can enjoy together?

  36. How could we improve our sex life?

  37. Do you feel comfortable talking with me about your sexual needs? If not, why?

  38. How can I make you feel more desirable and sexy?

  39. How much non-sexual affection would you like?

  40. What kind of affection feels loving and good to you?

  41. When do you need affection the most?

  42. How much affection in public are you comfortable with?

  43. What activities and interests can we develop that will bring us closer?

  44. What could I do that would cause you to pull away from me?

  45. Who do we know that has the kind of intimacy we want?

  46. When do you feel the most connected to me?

  47. What are the life lessons I can learn from you?

  48. What kind of memories do we want to create together?

  49. What will be the early warning signs that our relationship is in trouble?

  50. What do you think makes our relationship special?

  51. Where are you unwilling to compromise?

  52. What are your deepest dreams and desires for yourself and for us?

  53. What should we do if we start to lose our emotional closeness?

  54. Do I have any personal habits that get on your nerves? If so, what are they?

  55. How should I let you know about a habit of yours that bothers me?

  56. Do you have any bad habits you feel you must hide from me?

  57. What positive habits could we work on together?

  58. Are you comfortable with my hygiene and self-care? If not, what makes you uncomfortable?

  59. How can we be more accepting of areas of incompatibility with our habits?

  60. What bad relationship habits have we developed that need to change?

  61. What do I say or do that really pushes your buttons?

  62. What seems to be the recurring theme or themes in our conflict?

  63. What makes you feel heard and understood when we have conflict?

  64. When is the best time for us to resolve conflict?

  65. How can you best manage anger or frustration so we can talk calmly?

  66. What do you see as the major differences between us in the way we handle conflict?

  67. What are your deepest wounds from the past and how can I support you there?

  68. What pain or wounds from past relationships might be impacting our relationship?

  69. What do I unconsciously do that triggers pain from the past?

  70. How can I make you feel safe to be vulnerable about your pain and fears?

  71. What steps are you willing to take to heal from the past?

  72. How much time do you think is optimal for us to spend together as a couple?

  73. On a typical day, how would you like us to spend time together?

  74. How much alone time do you need?

  75. How can I let you know I need alone time without hurting your feelings?

  76. If we differ on the amount of time we need alone, how can we compromise?

  77. How much time do you want to spend with your friends?

  78. Do I have any friends you don’t like or feel uncomfortable around? If so, why?

  79. How often should we spend time with friends as couples?

  80. How do you feel about me having friends who are the opposite sex?

  81. Do you feel jealous of any of my friendships, and if so, why?

  82. How can we become better friends to each other?

  83. What holidays or traditions do you feel strongly we spend with your extended family?

  84. How would you like me to handle it, if someone in my family says or does something to offend you, in person or behind your back?

  85. What is your rule as a couple about discussing marital problems with extended family?

  86. What should we do as a couple to enhance our spiritual lives together?

  87. What are your long-term financial goals for us?

  88. What causes you the most worry or frustration about money now?

  89. How can I support you during a time of crisis?

  90. If you didn’t have to work, how would you spend your time?

  91. If we didn’t live in this city, where would you like to live?

  92. If we won the lottery, what would you want to do with the money?

  93. What are ten things on your bucket list?

  94. What life crisis do you fear the most? Why?

  95. How should we handle it if we have a disagreement about money?

  96. What do you want to do differently from your parents?

  97. What do you feel most proud of?

  98. What kind of legacy do we want to leave our children and the world?

  99. What do you see us doing during our retirement years?

  100. How can we continue to improve our relationship and become closer, kinder, and more intimate?


Good luck! And see you in the next post.

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