Learning to leave well is crucial to living well - that is the message local charity Both Sides, Now wants to spread.

More than just ensuring beneficiaries are able to live well, the project wants to facilitate the experience of death and dying.

Started in 2013, the group uses art and drama to spark conversations about death and dying, making the taboo topic more approachable.

The project sees several groups collaborating - across healthcare, community and the arts.

Co-presented by the Lien Foundation, Ang Chin Moh Foundation, Drama Box and ArtsWok Collaborative, the initiative is supported by Khoo Teck Puat Hospital and Montfort Care.

This year's iteration kicked off with the project's flagship performance, a puppet show titled The Wind Came Home.

Featuring an ageing couple represented by a thermos and a food container, the show tackles the topics of disease, physical decline and death with a light-hearted touch.

From dementia to adult diapers, the 30-minute puppet show created by Drama Box did not shy away from uncomfortable topics, and elicited not tears but laughter.

Artistic director Kok Heng Leun, who turns 51 this year, said: "Death and dying is such an unavoidable part of being human and living, but the only times we talk about it is in the hospital or doctor's office.

"Should we not take the topic out of such bleak and depressing places and into the communities and homes where people are comfortable and happy?"

At a performance held in a public amphitheatre next to Chong Pang Food Centre on Oct 20, about 70 participants spanning all ages gathered to watch the show.

Madam Kong Yat Chiu, 66, who took her sister along with her this year, said she had been attending the initiative's events since last year. The shows are organised several times a year.

She said in Mandarin: "It is so important for us to understand more about dying, so we can all prepare better for our own deaths.

"As we age, there is no denying that we will die. Instead of shying from it, talking about death will allow us to try to ensure we can die and have our deaths dealt with in the way we want."

The evening also included a sing-along session, a short film and craft projects.

In order to facilitate conversations, the attendees sat around a round table with volunteers who encouraged participants to converse.

The programme has targeted the areas of Chong Pang and Telok Blangah, where it has local partners.

The initiative has seen three runs in the past four years, each with one-off activities.

This year, the charity will be expanding its programme into workshops, to encourage communities to talk about mortality.

Over the next two years, the group will organise a series of talks and workshops called How Do You Say It. The two-part programme will teach participants, who must be aged 18 years and up, about dealing with end-of-life matters such as the medical, legal, emotional and social aspects of dying. They will also learn skills on how to talk about and prepare for these issues.

The group will also be putting up two interactive theatre pieces.

Exit features two families struggling to cope as they face illness and death. The audience can jump in and change the characters' course of action.

A second piece, tentatively titled The Art of Dying, has the audience being involved in the performance as characters themselves and able to enter into a dialogue about end-of-life concerns.

Both Sides, Now will also be bringing the conversation to a wider platform by setting up an art installation. A group of seniors will work with artists to create a series of art projects to be exhibited, including a legacy blanket.

Mr Kok said the seniors will make patchwork blankets to symbolise the "stitching together of their many experiences and stories".

He added: "The blanket was chosen to represent warmth and comfort, and remove the stigma that death must be cold and lonely."

These installations will be displayed in an effort to get the wider public to start thinking and talking about death and dying.

Ms Angeline Cheong, 42, volunteer manager for Both Sides, Now, said: "In my own experience, I know how much smoother and less unhappy a death can be if the family had been able to talk about it beforehand."

She said: "When my grandmother died last year, we were not able to be fully present for the last moments of her life because there had been no preparation and we were stressing about details like what to dress her in and what photo.

"If we had discussed it before, we would have known what she wanted and would not have had to argue about it at a moment when we were all grieving."