Maureen Pollard interviews Shawn about her experience with her grandmother choosing a medically assisted death. They discuss how Medical Assistance In Dying (MAID) is new to Canada, so "there is no playbook to tell people what you're supposed to say, how they're supposed to react". Shawn explains the benefits to having a family member pass away via MAID, how she didn't have to watch her grandmother decline and knew without a doubt that this is what she wanted, as legally people have to be mentally competent right up until the very end. They also discuss how much it helps to talk about this process, and how important it is to do so now in order for this conversation to become normalized for people in the future.

Maureen Pollard interviews Michelle about her experience losing both of her parents. They discuss how, after her father was diagnosed with cancer and passed away, Michelle did not deal with her feelings as her role was to help her mother and be her support. Years later, when her mother died unexpectedly, Michelle realized that "all of these pieces that I wasn't able to deal with from my dad, were still sitting there, they were still sitting there as I tried to deal with my mother's death". As a Catholic, Michelle also struggled with feelings of blame due to religious expectations on top of the powerful pain of grief. They also discuss how much it helps to share stories of her parents with her daughter and on platforms like Facebook where she can connect with other people who knew them, as well as the importance of humour to help ease that powerful pain.

Maureen Pollard interviews Melissa about her experience of losing her grandmother. They discuss how it sometimes feels more socially appropriate to hide behind a smile when grieving a loss, how feelings of grief are hard to be with, and how it's hard for others to be with us when we're in those feelings. Melissa talks about how she hid behind that 'perfectly packaged grief story' even though grief "is not pretty - it's messy, it's anger, it's sadness, it's heartbreak". They discuss how important it is to connect with other people who are grieving, who will sit with you and allow you to be a mess, and how communities like Grief.org help people to feel less alone in their grief.

Maureen Pollard interviews Gillian who, at only 28 years old, has experienced the loss of both of her parents. They discuss the contrasting challenges between slowly losing her father to cancer (predictable loss) and suddenly losing her mother to pneumonia (unpredictable loss) just ten years later. They talk about the drastic differences between how she grieved outwardly for her Dad in what she defined as a healthy way - channeling grief through positive things - versus how grieving for her Mom was completely inward: "it never felt like there was a place to put my grief, there was that feeling of being a little frozen and maybe a little bit numb". They also discuss how there is no right way to grieve, how important it is to give yourself the permission to mourn people differently and to meet each loss with the kind of grief that suits you and serves you.

Maureen Pollard interviews Joanie about her experience of losing her husband to pancreatic cancer. They discuss how, as a couple, they were so in sync that when he passed it felt as if half of her was gone and she didn't know who she was anymore; how she had to face her own mortality and struggled to find purpose to carry on. "You identify so deeply and profoundly with your partner that nothing makes any sense." They also discuss how the people she thought would be there weren't, but that the people who stepped up surprised her and felt like a gift in such a lonely, scary time.

Maureen Pollard interviews Krista about her experience of suicide loss. They discuss the complexities of losing her husband in this way; the challenges in remembering happy times, of having many unanswered questions, and in "remembering his life as so much more than his death". They also discuss the hurdles Krista is constantly jumping in the course of accepting and adjusting to what happened, how important it is to connect with those who can share in her experience of loss, and how "the greatest grief translates to the greatest love for somebody".

Author of "The Twentieth Year: A Memoir of Miscarriage", Maureen Pollard, interviews Sharron about her experiences of early pregnancy loss, which lead to the loss of her relationship. They discuss feelings of isolation, shame and embarrassment: "I didn't feel like they were valid losses". They also discuss the importance of seeking support among others with shared experiences, and how "The Twentieth Year" helped Sharron to finally feel that her grief was valid, and taught her that it is "never too late to grieve".