Some mornings just start with a vibe—and today’s was pure chaos meets wisdom.
and I opened The Daily Whatever Show laughing about my cat Ripley’s 10th birthday (she’s a literal daemon, His Dark Materials-style, claws and all). From there we jumped straight into a day that felt equal parts heartfelt and hilarious, with advice, embarrassing stories, and a few philosophical detours through love, grief, and toilet paper theft.We started with stories of famous-people fumbles—my awkward “Hi, Jeff Bezos—how are you? …how are you?” moment, and Dana’s beautifully mortifying exchange with Rhett Miller of the Old 97s. Turns out, both of us have an Olympic-level talent for public humiliation and for turning it into content. From there we turned confessional, moving into the show’s theme: advice from two allegedly wise GenXers who know better, but often don’t do better.
We talked about grudges—how we don’t have many, but the ones we do last forever. I confessed to perfecting the art of “social invisibility”—when I decide someone is dead to me, they basically cease to exist in the room. Dana admitted she needs her friends to share her grudges like emotional union cards. None of it’s healthy. All of it’s true.
Then the audience started sending in questions, and the show deepened fast. One listener asked what to do when a family member discovers your Substack and you want to write about painful past truths. My answer: write it anyway—it’s your one rare and precious life. Dana, ever the memoirist, added the essential caveat: tell your truth, but be ready for the reaction. It’s not wrong to protect your peace until you’re ready to handle the fallout.
From there, the questions just kept coming. A parent with an estranged 17-year-old. A toilet-paper-stealing boyfriend. A sparkless relationship. A grieving partner wondering when it’s “okay” to love again. We held space for all of it—with a mix of humor, empathy, and blunt honesty. Dana’s advice on the estranged teen was heartbreakingly good: keep the door open, send love without pressure, and, if possible, set a gentle date to check back in. My own spin: give them space, but remove the “chasing” dynamic—make love the stable constant they can return to.
The relationship questions brought out both our inner Dan Savages. The verdict: toilet-paper theft is an amber flag; lack of spark after five months is a red one. And when it comes to dating after loss—there’s no clock on grief. The heart, as Dana beautifully put it, is a terrible timekeeper.
Somewhere between laughter and heartbreak, between Ripley’s birthday hat and the story of a widow’s memorial turning into a Hinge date, we realized this is exactly what The Daily Whatever Show is meant to be: a space where joy, pain, and absurdity all share the mic.
We’ll be back tomorrow with
(and apparently a light dose of consensual dom energy), followed by on Friday and on Saturday.Until then—love you, mean it.
Thank you
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,
