Talking about death, dying and bereavement can feel overwhelming, but these are essential conversations rooted in love and compassion. Breaking the silence, especially if you have been brought up in an environment where such topics are considered taboo or simply swept under the carpet, can be challenging.

Approach these conversations with sensitivity, framing them as acts of love rather than fear or guilt. It’s about making sure that, when the time comes, everyone’s wishes are known and respected, and we reclaim our dignity at the end-of-life. The most important thing is to listen with lots of patience, giving each person the time they need to express their emotions and reflect on their fears. Ultimately, these talks are about ensuring peace of mind, honoring one another, and embracing the inevitable with love, understanding, and lots of patience.

TLDR: Three key things to consider are

1. Time - choose an appropriate schedule to start these conversations. If you are “successful” in getting the door opened, you don’t want to have to cut it short because you have another appointment lined up

2. Context - under what circumstances are you raising these conversations ? What is the frame of mind of your loved one?

3. Patience - if at first you don’t succeed, try and try again. You don’t know what seeds you have sowed by starting to raise these conversations.

Here’s a list of possibilities to explore.

Life Contexts

• Sharing personal experience: visiting a sick relative, recent bereavement experience of close friend, as openings to discuss thoughts on life & death

• After a diagnosis: If you or a loved one experiences a health scare, it’s an appropriate time to discuss preferences for care and support.

Media & Movies

• News or Media Content: Referencing a news story or article that touches on end-of-life themes, or the passing of a celebrity. For eg. “Let’s Talk About Death: I want to be a tree when I die”

• Movies, Netflix shows or even animated films highlighting themes on death, dying or bereavement can be good conversation starters

Family Gatherings

• Family discussions: Use family gatherings to talk about end-of-life wishes eg. when elders start to reminisce or talk about their friends who are no longer around

• Milestone events: Birthdays, anniversaries, or even seventh month.

In Quiet, Private Moments:

• One-on-one conversations: Sharing your thoughts during a quiet moment with a family member or friend can feel more intimate and less overwhelming. If the person initiates the conversation, take the opportunity to continue, rather than dismissing them.

• Walks or shared activities: Allow for more natural conversations when paired with a relaxed activity, such as going jogging, day out at the beach, bringing the pet out for a walk

• Depending on the nature of your loved ones, consider scheduling a time to discuss this so that they are not caught unaware and come prepared for the discussion. (We are told that some men prefer this. True ?)

Frame it as care and preparation

• Express it as concern, rather than guilt: Emphasize that having these conversations is about caring for each other and making things easier during difficult times.

• Focus on practicality: Approach it as a planning discussion, ensuring everyone knows where important documents are and importance of honouring their wishes. eg. scattering ashes in the sea

Use humor or light-heartedness

• Inject humor (where appropriate) : Sometimes, starting with a light-hearted or humorous comment about the unpredictability of life can make the conversation more approachable. eg. sending internet memes

• Cultural references: Referencing cultural superstitions or rituals can open the door to more serious discussions. eg. going to haw par villa

Address fears and misconceptions

• Clarify and ask questions: Some family members may resist these conversations out of fear. Provide the necessary reassurances based on their fear (which are very real!)

• Seek to understand concerns, be patient!

• Never dismiss their fears.

“Outsourcing” - Tools, documents, relatives

• Join group events like "Death Over Dim Sum" to learn how to initiate the conversation in a compassionate and gentle way or educational workshops like Last Aid

• Review documents like wills, advance care planning, or lasting powers of attorney together can open up deeper discussions eg. “I’m going to do my LPA, would you like to do it together?”

• Ask close relatives or family friends to help initiate the conversations, for eg. cousin, niece/nephew or even brother or sister-in-law. This may be easier than the emotional charge attached to the sensitivity of these conversations when raised by the direct family. These close relatives or family friends are familiar enough to your loved one, yet there may be some distance which can provide the necessary objectivity.