And, I'm on an AI role. I've worked with a couple AIs to create a set of questions that will my husband and I plan our future. My plan is to bring these up over a few dinners with my Husband. There are many questions here and it will take time.  

Session 1: Connection and Appreciation

Goal: Reconnect emotionally and appreciate each other’s uniqueness.

What’s something about me you feel people don’t see—but you do?

1. When did you first feel truly at home with me?
2. What habits of mine make you feel cared for?
3. How do you think our relationship has changed over the last 10 years?
4. What do you wish we did together more often?
5. What’s something you feel we’ve overcome together?
6. When was the last time I made you feel really understood?

Session 2: Shared Dreams and Divergences


Goal: Uncover each partner’s ideal retirement lifestyle and negotiate shared rhythms.

1. What does your ideal day look like in retirement—from waking up to going to bed?
2. What’s something I enjoy that you don’t—but you’ve tried (or would be willing to try) for my sake?
3. What’s something you wish I’d try or do more often with you—even if it’s outside my comfort zone?
4. What kind of social life do you want in retirement? What would feel “just right” to you?
5. What’s your biggest hope for our retirement life? What’s your biggest worry?
6. If we traveled together regularly—say, two times a year? Four?—where would you want to go, and why?
7. What home-based project or hobby would you like to dive deeper into?
8. How can we support each other in making time for the things we love—even when they’re different?

Session 3: Money, Health, and Caregiving

Goal: Build clarity and partnership around future responsibilities and resources—without losing your sense of “us.”

1. What are you most willing to cut back on in retirement—and what feels non-negotiable?
2. What health changes do you anticipate over the next 10 years, and what worries you most? How can we support each other through those changes—emotionally and practically?
3. What role do you want to play in caring for our parent(s) over the next 5 years? What do you hope I understand about that?
4. How do you feel about the idea of needing care yourself someday? How can we prepare emotionally?
5. If we needed to adjust our home or routines for health reasons, what would feel supportive vs. stifling?
6. What financial or legal steps do we still need to take to protect each other and our families?
7. How can we keep conversations about money and aging open, loving, and low-drama?

Session 4: Legacy, Meaning, and How We Spend Our Time

Goal: Shape your time in retirement around fulfillment, contribution, and connection.

1. What gives your life meaning right now? How has that changed in the last decade?
2. Are there skills or passions you’ve never had time to pursue that you'd like to explore now?
3. What does “a good use of time” mean to you in retirement?
4. What kind of creative or intellectual stimulation would you like to keep in your life?
5. How can we support each other in doing things separately that still strengthen our bond?
6. What’s one thing you’d love for us to try just once this year—no matter how small or silly?

Session 5: Rituals, Intimacy, and Everyday Connection

Goal: Weave emotional closeness into daily life through small, intentional choices.

1. What small things do I do that make you feel loved?
2. What are our current rituals that bring us closer—and which ones have faded that you miss?
3. What kind of physical affection feels most nourishing to you these days?
4. What does “intimacy” mean to you now? How has that changed over time?
5. What’s a weekly ritual we could start that would help us feel more like a team?
6. When you want to feel closer to me, what do you hope I’ll notice or do?
7. What’s something you’d like to experience together in the next 12 months that we haven’t done before?
8. How can we keep reminding ourselves that our relationship is still evolving, still worth growing?

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