21 Thoughtful Questions to Foster Deeper Connections with Your Older Loved Ones

A study commissioned by KYN shows that two-thirds of British people who have lost older loved ones wish they had engaged in more meaningful conversations to truly understand the essence of who they were. Among the participants, 29% attributed this circumstance to insufficient time spent together, 26% expressed uncertainty about initiating these conversations, and 24% expressed concerns about causing discomfort by delving into their relatives' pasts.

As we grow older, it's unfortunately common to focus solely on a person's age or health and overlook them as a person with a life well-lived. When spending time with an older loved one, it's important to remember that their past experiences, current interests, and future aspirations are just as significant as ever and that these aspects of their life continue to shape who they are and may have shaped who we are today.

In a collaborative effort to spark meaningful conversations, KYN has partnered with psychologist Honey Langcaster-James to create a set of 21 questions designed to foster genuine, heartfelt connections. Honey Langcaster-James is a prominent and insightful psychologist who brings her expertise to the forefront of meaningful human interactions. Honey is a well-known figure in the media and entertainment industries, renowned for her expertise as a TV Psychologist and Psychological Therapist for Film & Television Productions. Honey's influence extends beyond the screen, as she collaborates with multinational organisations and well-known brands. Her partnership with KYN aims to bridge the gap between generations and encourage profound dialogues. A collection of 21 questions was designed to foster authentic and heartfelt connections, rekindling a genuine understanding of one another.

These questions can be asked in person or written in a letter, but the crucial aspect is to express genuine interest and provide your loved one with a warm invitation to share their thoughts and experiences with you. For those uncertain about where to start, grappling with time constraints, or hesitant to potentially stir negative emotions, Honey Langcaster-James suggests beginning with question 1. Let each interaction become a cherished journey of understanding and appreciation, bridging gaps and celebrating the lives well-lived.

1. What have you learned over the course of your life that you can pass on to me - what do you think it would be good for me to know?
2. Tell me about some of your earliest memories.
3. Where were you born and raised, and what was it like there while you were growing up?
4. What was your childhood like overall and what is your fondest memory from when you were young?
5. What were your school days like and what did you most enjoy learning about at school?
6. What hobbies and interests did you have, and what did you most enjoying doing in your free time when you were younger?
7. What is the most surprising thing you think people don’t know about you?
8. What was your favourite music or artist when you were growing up and why?
9. What has been the most interesting job you’ve ever done?
10. Who have you loved during your life, how did you first meet them, and how did your love story unfold?
11. What is the most significant historical moment you lived through or witnessed and what did you think about it all?
12. What was your favourite decade overall and why?
13. Who were your role models and who influenced you in your life and why?
14. Where was the most interesting place you ever travelled to and what did you make of the place?
15. What was the most challenging obstacle you had to overcome in your life and what did you learn from that?
16. What is your proudest accomplishment in life and why?
17. Looking back, what advice would you give to your younger self?
18. What’s the best book you ever read and why?
19. What have been the biggest changes you've seen throughout your lifetime?
20. What’s the funniest thing that ever happened in your life and what makes you laugh?
21. What are your hopes for the future and how would you most like to be remembered?