Today’s The Daily Whatever Show was a classic bestie episode, easing into the morning together with no guest, no rigid agenda—just the kind of wide-ranging conversation that moves naturally from the personal to the political and back again.
It opened with small, grounding details. I was juggling dog logistics, smudged glasses, and an upcoming eye appointment before settling into something deeper and more resonant.
The emotional spine of the episode came from my essay idea-in-progress: “Gen X dating is grief.”
I talked through it not as a slogan, but as a lived reality: the quiet accumulation of loss that underlies dating later in life. Whether it’s the end of a marriage, the absence of a long-term partnership, or the chronic grief of wanting something that never quite arrives—we are all grieving.
What made it land was the specificity: the distinction between acute grief and the long, background grief that doesn’t announce itself but never really leaves. Lawrence added his own perspective, letting the idea breathe rather than turning it into a neat takeaway. Hopefully a full essay on this topic will be forthcoming… soon. Adding it to the to-do list.
From there, the conversation widened into culture and technology. Lawrence and I traded stories about AI’s growing role in creative and technical work, including a chilling anecdote about a developer using Ralph to replicate entire software products for the cost of ten dollars an hour.
The tone stayed curious but uneasy, especially as they connected that shift to the current wave of tech layoffs and the uncomfortable sense that some industries are being hollowed out in real time.
The back half of the show centered on music, specifically, the sudden resurgence of protest songs.
Lawrence and I introduced two brand-new releases: Bruce Springsteen’s “Streets of Minneapolis” and Billy Bragg’s “City of Heroes,” both written and released within days of the killings of Alex Pretti and Renee Good in Minneapolis.
The contrast between the songs became part of the discussion: Springsteen’s measured, mournful documentation versus Bragg’s raw, confrontational call to action. Hearing the lyrics out loud on the show made the moment feel immediate and communal, less like commentary and more like a witness to a movement.
Have a listen, and let us know in the comments which is your favorite.
(FWIW, I’m Team Billy, and Lawrence Winnerman is Team Bruce.)
((But really, we’re both Team OMG These Songs Are Incredible.))
Thank you Ellie Leonard, Stephanie G Wilson, PhD, Cat, Polly Walker Blakemore, Melissa Corrigan, she/her, Yanni Hamburger, Jason Odell, Eric Lullove and Karen Marie Shelton moderating The Whatever chat.
We’ll be back tomorrow bright and early for The Daily Whatever Show for Fucked-up Friday with Kait Justice.
We love you all—truly!—mean it.
