Zoomer vs Boomer

The second part of our discussion with Lindsay, a 40‑year‑old woman, dives into marriage, divorce, and stepping back into modern dating — revealing the lessons, surprises, and second‑chapter courage that come with starting over.

Lindsay got married at nineteen. The church she grew up in said that's what you do, so she did it — and she stayed for fifteen years.

At thirty-four she had the thought that ended it: I am going to have to be with him after the kids leave.

She's forty now. Six years divorced, two kids, and back in a dating world that didn't exist the last time she was single. In this episode she walks us through all of it — the marriage, the faith she's since left, the exact moment it broke, and what she built afterward. She's unusually clear about what she got wrong herself, and about the part nobody warned her was coming.

One of us has lived it. The other has Googled it. This week, Lindsay is the one who lived it.

Three generations discuss the world we live in from their own perspectives: icks, red-flags and attractions.

Three generations discuss the world we live in from their own perspectives. We ended up having quite a bit of controversy.

We apologize for not releasing any new episodes over the past few weeks. Between Presley's law school finals and Bill's AI startup, we just couldn't find the time. In this episode, we recap our last conversation and dive into a discussion about relationships.

Picking up where our Valentine's episode left off, this is the first of three chaos‑filled installments where Austin—our fearless 20‑something—spills his 'icks,' red flags, and absolute deal‑breakers.

"Revenge is a dish best served cold." After the Valentine's episode—our chaotic detour into Gen Z "icks" and red flags, where Bill practically dry‑heaved at the mere idea of dating—he came back swinging. This time, Bill didn't just serve Presley one dish… he rolled out an entire tasting menu of payback.

It was our boss Verne's birthday, and Presley's good‑natured determination dragged Bill—despite his fatigue and total lack of interest—on a late‑night shopping trip.

The suffering continues. Bill's boomer brain short‑circuits as Presley unleashes yet another round of her infamous 'icks.' Her heart is absolutely in the right place—unfortunately, her advice only pushes Bill further toward the Dark Side.

What is an "ick?" Presley, the sweet and ever‑supportive cohost, valiantly tries to steer Bill's love life with advice and encouragement. Predictably, it goes off the rails almost immediately — and she absolutely refuses to give up.