In 2003, Demi Moore and Ashton Kutcher sent shockwaves through Hollywood when they debuted their unlikely romance. What was originally thought of as a cougar publicity stunt, turned into one of the most serious celebrity couples of the 2000s.

Join Jill as she deeps dives all the twist and turns of one of the most notorious couples of the 21st century. From "MOD" to Kabbalah, we cover every corner of this wild ride. And some layers are so unbelievable, you may feel like you're being punk'd.

Follow the podcast on Instagram @DivingBoredPod!

Before fashion influencers, before Instagram, before sponsored posts...there was Rachel Zoe.

Rachel Zoe didn’t just style celebrities, she helped shape how fame, fashion, and visibility worked in the 2000s. Join Jill as we unpack Rachel’s rise from behind-the-scenes stylist to cultural power player, the paparazzi era she mastered, the Zoebots, the weight-scandal scapegoating, and how her clients became the original influencers before influencer culture even existed.

From Nicole Richie's iconic image makeover to The Rachel Zoe Project and her full circle return on The Real Housewives of Beverly Hills, we'll deep dive into legacy, blame, power, and why we’re still talking about Rachel Zoe decades later. It's going to be "bananas!"

Follow the podcast on Instagram @DivingBoredPod!

This is a story about a girl named Britney...and Kevin.

Join Jill for Part 2 of the Britney and Kevin saga. No stone goes unturned as we discuss Britney's journey through 2007 and 2008, her conservatorship, and how she persevered to gain freedom. She's stronger than yesterday, and now it's nothing but her way.

We also ask Kevin to put his thinking fedora on to answer some hard hitting questions! Don't miss it!

Follow the podcast on Instagram @divingboredpod

It's getting hectic in here, it's getting chaotic.

Diving Bored is back! And to commemorate the momentous occasion we're diving into two of the biggest star crossed lovers of our time: Britney Spears and Kevin Federline. In this two part series, we will dive into everything. From the Chaotic era, to the conservatorship, no stone will go unturned.

Join Jill as she dives into the relationship that embodied the chaos of the early 2000s. Was it love? Or was it just a tabloid, media circus? So strap the baby in the carseat, because we're about to a take a full speed ride down memory lane.

Follow the podcast on instagram at @DivingBoredPod

Feel the rain on your skin, we are officially deep diving one of the most infamous couples of our time: Spencer Pratt and Heidi Montag! We discuss it all. From their individual backstories, to them wreaking havoc all over Hollywood together, we pay homage to two of reality TV's original villains. We also discuss their recent redemption arc and how friends of the past are rallying in support. What will happen next? Well, the rest is still unwritten.

Follow the podcast on Insta @divingboredpod

Ways to Support LA Fire Victims:

FireAidLA

Global Empowerment Mission

Los Angeles Regional Food Bank

California Fire Foundation

World Central Kitchen

American Red Cross

California Community Foundation

Check underneath the tree because a new gift awaits, in the form of a deep dive on one of the biggest icons of our time, Mariah Carey. There are no reindeer games on this holiday episode, as we unpack it all. From Mariah's humble beginnings, to the Glitter fiasco, to one of the greatest comebacks of the 21st century, she is truly the gift that keeps on giving. So make your list and check it twice, because all I want for Christmas is a deep dive on the Diving Bored Podcast!

Follow the podcast on instagram @DivingBoredPod!

Happy Holidays everyone and a peaceful and prosperous New Year!

In 2003, Nicole Richie premiered on our television screens in The Simple Life and became a household name sooner than you could say "sanasa". But as Nicole's fame grew, life became not so simple. Join Jill as she dives into Nicole's early years, her meteoric rise to fame, 2000s toxic tabloid culture and so much more. Jill also does several dramatic reads including one on the iconic Memorial Day party invitation. You are cordially invite to the deep dive of Nicole Richie!

Follow the podcast on instagram @divingboredpod

Let me hear you say "yeahhhh boi!!" We have our first ever interview on the Diving Bored podcast and we're starting off as strong as ever with the iconic and legendary, Flavor Flav! Join Jill as her and Flav kick back and discuss everything from Public Enemy to Taylor Swift. We also discuss hip hop's early days, Flavor of Love, the US Women's Water Polo team and so much more! Get your clocks ready and dive in with the greatest hype man of our time.

Follow the podcast on Instagram @divingboredpod