Most families don’t realize what questions matter until they’re already in the middle of a decision.
After years working inside senior living — walking alongside residents and families during tours, transitions, and tough conversations — I’ve seen the same thing again and again:
Families care deeply, but they don’t always know what to ask or when to ask it.
These are the questions I wish families felt empowered to ask earlier — not out of fear, but out of preparation. Asking the right questions can change the entire experience and help families make decisions with clarity instead of urgency.
I hope you enjoy the letter below. 🙂
Hello, sweetie.
Yes, I’m talking to you — my wonderful grown-up child who’s juggling work, bills, and a family of your own. I see you trying your best, and I love you for it. But there’s something that’s been on my mind lately, and it’s not just where I put my reading glasses this time (although, seriously, if you find them, let me know).
It’s about my future. About senior living. About what happens next.
You see, a lot of us aging folks are thinking about retirement communities, assisted living, downsizing, or staying put. But here’s the catch: we’re waiting for you to start the conversation… and you’re waiting for us. So let’s break that cycle, shall we?
Let me share the 10 questions I secretly wish you’d ask me — questions that would help us both figure out the best path forward with love, humor, and dignity.
1. “Mom, how do you feel about where you’re living now?”
This one’s big. Not just whether I can climb the stairs or mow the lawn — but whether I feel lonely here. Whether I miss having a social life. Or if I’m starting to feel a little trapped in a house that once felt like home but now feels like a museum of memories and creaky floorboards.
Let’s talk about what feels right, not just what’s practical.
2. “Would you like to live somewhere with more people your age?”
You know, I do miss chatting with people who understand my references to Dick Van Dyke and don’t blink twice when I say “rotary phone.” A retirement community isn’t just about care — it’s about community. Bridge games, coffee mornings, and gossiping about the new guy in Apartment 2B? That’s living.
3. “What scares you the most about aging?”
Now, this one takes guts — for both of us.
The truth? I worry about losing my independence. About being a burden. About the day my body gives out before my mind does… or the other way around. When you ask this question, you open the door for me to be vulnerable. And that’s a gift.
4. “What kind of help do you think you’ll need in the next 5–10 years?”
I may not need a nurse right now, but what about in five years? Or ten? I know some senior living communities offer levels of care, meaning I can start in independent living and move into assisted care later. That kind of future-proofing is comforting.
Let’s plan for the future while we can laugh about it.
(These are exactly the kinds of conversations we help families prepare for during a Next Step Plan™ session — before emotions or urgency take over.)
5. “Is there something about your home that makes life harder now?”
The stairs. The bathtub. The lack of grab bars. The snow that doesn’t shovel itself. These things used to be manageable — now they’re mini mountains. Asking this shows me you see the effort it takes just to keep up.
6. “Have you looked at any senior living options? Would you like me to go with you?”
You know what’s scary? Walking into a senior living tour alone and feeling like I don’t belong yet. Going with you would help me see this not as an ending, but a beginning. Let’s grab some coffee, and maybe a brochure, and see where it leads.
7. “If something ever happened to you, how would you want things handled?”
Okay, this one’s not fun. But planning things like a medical directive, power of attorney, or even just who feeds the cat if I fall ill — that’s peace of mind.
It’s not being morbid. It’s being grown-ups.
8. “Would you rather age in place, or move to a retirement community?”
There’s no one-size-fits-all answer. Some of us want to stay home with in-home care. Others want new adventures, activities, and friends nearby. Asking this shows me that you’re not trying to put me somewhere — you’re trying to support my choice.
9. “What would your dream retirement look like?”
Would I like to live near the beach? Have a little garden patio? Join a choir or a yoga class? Let’s dream a little. Because this chapter of life shouldn’t be about decline — it should be about delight.
10. “Can we revisit this conversation again soon?”
Oh, bless you for this one. This conversation isn’t a one-time chat — it’s a journey. Check in with me every few months, and let’s keep the dialogue open, honest, and warm.
We hope the above questions have helped and inspired you in some small way.
Our team has a considerable amount of insight into senior living and aging in place as we have actually lived in the communities that we managed.
It was both an honor and a pleasure to “do life” everyday with our residents. It was not easy at times, especially during the pandemic, but it had a profound effect on those of us who worked and lived along side our residents everyday.
The questions above and below are not just random questions and answers. These questions and answers came from talking with and listening to hundreds of older adults over several years who taught us so much about life and how they would like to live their lives.
Key takeaway: The most important four things you can do for your parent or loved one are as follows: Ask + Listen + Include + Support.
It will help make this journey one that is full of compassion, trust and love.
FAQs: Talking to Aging Parents About Senior Living
Q1: Why do aging parents avoid the topic of senior living?
Many fear losing their independence, being seen as “old,” or feeling like we’re being sent away. A gentle, open conversation can ease that fear.
Q2: What’s the best way to bring up senior living options without sounding pushy?
Start by asking how they feel — not what they need. Use empathy and curiosity, not pressure.
Q3: Are senior living communities just for people who need care?
No! Many are vibrant, social places for independent seniors who want convenience and community.
Q4: How can I tell if my parent might benefit from assisted living?
Look for signs like missed medications, trouble with stairs, or social isolation. Don’t jump to conclusions — talk first.
Q5: What should I say if my parent resists the idea of senior living?
Acknowledge their feelings. Then offer to explore options together — not as a decision, but as information gathering.
Q6: Is it better to talk about this before there’s a health crisis?
Absolutely. The best decisions are made when we’re calm, not in crisis mode.
Final Thoughts: Let’s Have the Talk — With Love, Not Fear (Conclusion from parent point of view)
Dear one, I know these conversations aren’t easy. But trust me — starting them now, when we’re both clear-headed and calm, is the best gift you can give.
So let’s talk. Not about what’s wrong — but about what could be right in the next chapter of my life.
I’m not fading away — I’m evolving. And I’d love for you to be part of the journey. ❤️
Knowing the right questions to ask is only part of the picture. Many families still struggle with when to ask them — and which path makes the most sense.
The Next Step Plan™ helps families slow things down and create a clear, personalized roadmap for staying home, downsizing, or exploring senior living — without pressure or rushed decisions.
👉 Learn more about the Next Step Plan™
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