Single in middle-age: Truth, grief & freedom

Single in middle-age: Truth, grief & freedom

From Beyond the basement by Chris Kenworthy

May 26, 2026 · 36 min

About this episode

An improvised exploration of the complexities of being single in middle age, addressing themes of grief, freedom, and self-discovery.

Come along for an improvised exploration of this strange, unexpected chapter of life: the grief of not being where I once expected to be, the freedom (and loneliness) of living outside the conventional script, and the quiet reality of building an unconventional life while many people around me are immersed in marriage, children, careers and family life. We’ll talk about the emotional texture of this experience - the sense that life is not supposed to look like this, the loss of structures I once assumed would hold me, and the way middle age seems to bring old wounds, deeper self-reflection and inner work to the surface. I also touch on friendship, solitude, self-reparenting, ageing, visibility, youthfulness, and the gifts that can come with knowing yourself more clearly. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriskenworthy.substack.com

People in this episode

Host: Chris Kenworthy

Topics covered

  • middle age
  • grief
  • freedom
  • self-reflection
  • friendship
  • solitude
  • self-reparenting

Keywords

  • middle age
  • grief
  • freedom
  • self-reflection
  • friendship
  • solitude
  • self-reparenting
  • loneliness
  • unconventional life
  • emotional texture

More episodes of Beyond the basement

Explore listener stats, chart rankings, contacts and more on the Beyond the basement podcast page.