How do I even bring this up?

Conversation Starters for talking to your parents or a loved one about aging and care.

Starting a serious conversation with a parent about aging can feel awkward and tricky. You don’t want to upset them, but you still need to plan.


These 15 conversation starters are a low-pressure way to open the door to future planning. Designed to be respectful, open-ended, and easy to say, each question helps you build trust, encourage dialogue, and take the first step toward creating a plan that supports their needs and your peace of mind.


Big Picture Conversation

  • Have you ever thought about what you’d want if something unexpected happened to your health?

(Gently introduces future planning without implying urgency.)

  • If you ever need help down the road, what would that look like for you?

(Shows you're interested in honoring their preferences.)

  • Do you have any preferences for where or how you want to live as you get older?

(Opens the door to talk about aging in place vs. care options.)

  • Would it be okay if we sat down one day soon to go over some basic information, just in case I ever need to help?

(Gives them a heads-up and choice, which builds trust.)


Health & Safety

  • How are you feeling about getting around the house lately? Any spots that feel tricky or unsafe?

(Eases into a home safety check without sounding critical)

  • Have you noticed it’s getting harder to keep track of medications or appointments?

(Gives them space to express challenges without shame.)

  • Would it be helpful if we reviewed your medical info together and wrote it down somewhere easy to find?

(Frames it as a gift of peace, not pressure.)

  • If there was a medical emergency, who would you want to speak for you if you couldn’t?

(Presents an important legal topic in a personal, caring way.)


Finances & Legal Planning

  • Do you have a will or power of attorney set up? I want to make sure your wishes are followed.

(Focuses on honoring their voice, not taking control.)

  • If bills ever became tough to manage, would you want help with that or would you want someone else to step in?

(Invites them to set boundaries and preferences before it’s urgent.)

  • If you ever needed more help, who else would you feel comfortable having around?
    (Reveals comfort levels with outside help or extended family.)
  • Where do you keep the important documents, like insurance or bank info, just in case someone needs to find them?

(Makes finding help easier in a crisis—without sounding intrusive.)


Trust & Connection

  • I want to understand that my goal is to help make things easier for you, not take control. Would it help if we started planning together?

(Reassures them this is a team effort, not a takeover.)

  • This isn’t easy for either of us, but I’d rather talk now than guess later about what you’d want.

(Shows empathy and a desire to do right by them.)

  • You’ve always taken care of me. I want to return the favor by making sure we’re prepared, just in case.

(Brings in love and gratitude without pressure.)


Bonus Questions

  • Is there anything you'd want us to do differently if your health changed suddenly?

(Opens the door to values-based planning.)


  • What does a good day look like for you now and how can we help keep those going?

(Helps align care with their daily happiness and routines.)


  • What matters most to you in terms of staying independent?

(Centers the conversation on their priorities, not just logistics.)


  • I read something recently about planning for the future. Have you and Mom/Dad talked about that at all?

(Makes the topic feel casual and timely, not awkward).