Life transitions can be both exciting and challenging, especially when they involve big changes for you and your partner. Whether it’s moving to a new city, switching careers, starting a family, or dealing with health changes, each new chapter brings opportunities to grow as a couple. Taking time to check in with each other through open, meaningful conversations can help you navigate these transitions and maintain a strong, resilient bond.

Here are 100 check-in questions that can guide you and your partner through various life changes. Use these questions to keep your connection strong, share your feelings, and support each other as you embark on new journeys together.

We also have some cute cards with the questions below which you can download, stick to your journal as you answer them. Find more conversation cards, game cards on our store here. Find these kind conversation on other blog posts.

Questions to Help Couples Navigate Life Transitions

Starting a New Chapter Together

1. What are you most looking forward to in this new phase of life?
2. What excites you most about this transition?
3. Is there anything about this change that makes you nervous?
4. How can we make this transition as smooth as possible?
5. What’s one thing we can do together to celebrate this new beginning?
6. What are your biggest hopes for us in this new chapter?
7. How can we support each other’s personal growth through this change?
8. How do you think this transition will impact our relationship?
9. What do you hope will stay the same for us during this change?
10. What are some new routines or traditions we can start together?

Moving to a New Home or City

11. How are you feeling about moving to a new place?
12. What are you most excited to explore in our new location?
13. How can we make our new space feel like home together?
14. What are you looking forward to leaving behind as we move?
15. What do you think you’ll miss most about our current home?
16. How can we support each other through any homesickness or adjustment?
17. Are there any activities you’d like us to do together in our new area?
18. What does “home” mean to you, and how can we create it?
19. What do you think will be the biggest challenge in our move?
20. How can we make moving less stressful for both of us?

Starting a New Job or Career Path

21. What excites you most about this new career direction?
22. How can we support each other’s professional goals?
23. What worries do you have about balancing work and personal time?
24. What would you like me to know about your workday or routine?
25. How can we stay connected with potentially different schedules?
26. What does work-life balance look like for you in this new role?
27. How can I help relieve work stress when it gets challenging?
28. What professional goals would you like to share with me?
29. Are there any new skills or hobbies you’d like to develop together?
30. How can we make time for quality moments together outside of work?

Parenthood and Growing Your Family

31. What excites you most about becoming parents?
32. What concerns do you have about parenthood?
33. How do you envision us sharing parenting responsibilities?
34. What values are most important for us to pass on to our child?
35. How can we support each other when things get challenging as new parents?
36. What’s one thing you’re looking forward to about being a parent?
37. How can we ensure we still have time for each other as a couple?
38. What kind of family traditions would you like to start?
39. How can we balance being partners and parents?
40. What role do you want family and friends to play in our child’s life?

Financial Changes or Challenges

41. How are you feeling about our current financial situation?
42. What are your biggest financial goals for the future?
43. How can we work together to achieve our financial goals?
44. What does financial security look like for you?
45. How can we avoid stress or disagreements over finances?
46. How can we communicate openly about money without judgment?
47. What are some things we can save up for together?
48. What would you like to prioritize in our budget?
49. How do you feel about combining or separating finances?
50. How can we celebrate financial wins or goals together?

Retirement and Lifestyle Changes

51. What are you most looking forward to in retirement?
52. What new hobbies or activities do you want to explore together?
53. How can we ensure a fulfilling daily routine in retirement?
54. How can we stay socially connected during this time?
55. What travel destinations or experiences do you want to prioritize?
56. How can we continue growing and learning together?
57. What are some ways we can stay active and healthy as we age?
58. How do you envision our living situation in the future?
59. What family or social activities do you want to focus on?
60. What does a fulfilling retirement look like for you?

Health Challenges or Adjustments

61. How are you feeling about this health journey we’re on?
62. What specific support do you need from me?
63. How can we both focus on maintaining a healthy lifestyle together?
64. What’s something that would help you feel more comfortable?
65. How can we maintain emotional resilience during this time?
66. What are some ways we can still enjoy quality time together?
67. Are there any lifestyle changes we should consider?
68. How can we communicate openly about any fears or concerns?
69. What are some positive steps we can take together for our health?
70. How can we make the most of each day, despite challenges?

Personal Growth and Individual Goals

71. What personal goals are you currently working on?
72. How can we support each other’s self-growth journeys?
73. What are some shared goals we want to work toward?
74. How do you feel about the balance between independence and togetherness?
75. How can we keep each other accountable in a supportive way?
76. Are there any activities or hobbies we’d like to explore together?
77. What are some ways we can encourage each other to try new things?
78. What does self-care mean for you, and how can I support it?
79. How do you feel about sharing goals and successes?
80. How can we maintain open communication as we grow individually?

Managing Stress and Overcoming Challenges

81. How are you feeling about the stress we’re experiencing right now?
82. What helps you feel relaxed or centered during stressful times?
83. What can I do to support you when you’re feeling overwhelmed?
84. How can we create a routine that reduces stress for both of us?
85. What activities help us feel connected during difficult times?
86. How can we prioritize rest and relaxation as a couple?
87. Are there specific things you need from me when you’re stressed?
88. How do you think we can balance responsibilities without burnout?
89. What helps you stay positive or motivated during hard times?
90. How can we make time for fun even when life feels heavy?

Nurturing Your Relationship Through Change

91. What do you appreciate most about our relationship right now?
92. How can we keep our connection strong through this transition?
93. What small gestures make you feel loved and appreciated?
94. How can we celebrate each other’s strengths during this time?
95. What are some things we can do to bring more joy into our routine?
96. How can we make each other feel seen and valued?
97. What does quality time look like for you in this phase of life?
98. What’s something new you’d like to try together?
99. How can we communicate more openly and effectively?
100. How do you envision our relationship growing through this transition?

Final Thoughts: Building Resilience and Connection

Checking in with each other is essential for keeping your relationship resilient and thriving through any life transition. By making time for these open, meaningful conversations, you’re investing in the foundation of your relationship. Remember, it’s normal to feel a range of emotions as you go through life changes, and being vulnerable with each other helps build trust and empathy.

Whether you’re starting a new adventure or facing unexpected challenges, these questions can help you maintain a strong connection and create a shared path forward. Life is full of transitions, but with a commitment to each other and open communication, you can face anything together.