We’re kicking off our Sibling Series with a powerful and heartfelt conversation with sisters Caroline and Natalie DeJean. You might remember Caroline from a past episode (celebrity stylist, cool girl, song-of-summer expert), and today she’s joined by her younger sister Natalie as they open up about the loss of their mom, Miss Liz, seven years ago.

This episode dives into all the complexities surrounding grief. How siblings can experience the same loss in totally different ways, and how layered family dynamics, including divorce and emotional distance, can shape the grieving process. Caroline and Natalie reflect on where their relationship stood with their mom at the time of her passing, and how they’ve each made peace with that in their own way.

We also get into some classic sibling rivalry, the evolving bond between sisters, and — of course — our annual Song of Summer debate. It’s messy, moving, and filled with moments that’ll make you laugh, nod along, and maybe even call your sibling afterward.

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Song of Summer (according to Spotify) 

One of us may be growing a baby but both of us are still figuring out how to grow around grief. In this episode, we catch up on Jill's third trimester—including her very on-brand babymoon in Hawaii—and talk about what it’s like preparing for new life while still carrying the absence of our brother Adam, something Holly didn’t have to navigate during her own pregnancy.

We also touch on the Knicks’ brief but incredibly long overdue playoff run (recorded in the blissful window before they lost), how siblings shape your whole identity, and why joy and grief seem to be on a shared custody schedule. Come for the baby updates, stay for the real talk.

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Peter Bretter trying to Forget Sarah Marshall 

In case you missed it, Mike White on Survivor: Season 37

Drop your buffs—it’s time for an episode decades in the making. This week, we’re joined by Bianca Maria Asumpte Immaculate Roses (yes, that’s her full legal name, and no, it did not fit on her high school diploma). She’s Jill’s best friend of nearly 30 years, a major PR pro, and now… a freshly torched contestant from Season 48 of Survivor. In this week's episode, we talk all things Fiji, sleep deprivation, and what it's like to have to leave the island while the game is still being played. Whether you're a fan of the premiere reality series or not, this conversation has it all. Beyond the game, this episode is a celebration of chosen family, shared Survivor obsessions, and the Roses-Shakoor bond—one that Adam cherished deeply. The tribe may have spoken… but now it’s Bianca’s turn.

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Catch up on CBS' Survivor 

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We were lucky enough to connect with someone who has truly shaped the grief space: Rebecca Soffer, author, community builder, and cofounder of Modern Loss. In this episode, we talk about how Rebecca turned her personal tragedy of losing both of her parents in her early 30s into a movement that normalizes grief in all its messy, complicated glory.

From her days producing The Colbert Report to creating one of Substack’s top newsletters on mental health, Rebecca has been using her voice to remind us that grief isn’t something to “get over”—it’s something we live with, grow through, and even connect around. We get into resilience (the real kind, not the Pinterest-quote kind), the myths we wish people would stop repeating (“everything happens for a reason” can take a seat), and how to hold space for both the pain and the absurdity of loss.

Whether you’re deep in it or supporting someone who is, this one’s for you.

Going Thru it 

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Modern Loss 

Subscribe to Modern Loss on Substack 

Modern Loss Handbook 

It’s a big week! The Knicks are in the playoffs, we’re celebrating one year of Going Thru It, and most importantly, we’re honoring our brother Adam on what would have been his 42nd birthday. While one of us is raising a (strong) Orange Jameson in his honor, the other is… not drinking at all, because — BREAKING NEWS — Jill is pregnant!

With life comes death, and with death comes rebirth. Through it all, there’s nothing but love. Join us as we keep going through it - together

⁠Going Thru It 

In this episode we catch up on all the chaos and comfort from the past few weeks—birthday bashes, LA adventures, and a whirlwind one-night trip to Vegas. The good news is there is some great culture happening right now to help get us thru it all. With Siblings Day upon us we get real about what this time of year brings up for us. The rush of memories, the weight of time passing since losing Adam, and the healing magic of a good playlist. Whether you're deep in grief or just here for some pop culture recs, this episode has a little bit of everything.

wearegoingthruit.com 

When it comes to having a baby, we all know someone who has gone thru it—IVF, IUI, surrogacy, egg and sperm donors, adoption. Parenthood looks different for everyone, and for our guests, Carrie Gordon and Phil Halpert, the road was anything but easy. They’ve faced loss, uncertainty, and grief at every turn—but their story is one of resilience, love, and ultimately, hope. This episode is for anyone who’s been on a similar path or simply needs a reminder that light can be found, even in the darkest moments.

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A true disruptor in IVF with an innovative outlook on fertility, Dr. Hade and Generation Next

THE baby whisperer, acupuncturist Christina Burns 

Dr. Jonathan Scher

Growing Generations: Surrogacy and Egg Donations 

Colorectal Cancer Awareness Month is here, and it sparks the question: why are SO many young people getting cancer?! TIME Magazine's recent cover story dives deep into this growing crisis, and so do we.....well, in our own way. In this week's episode we try to unpack what is causing this change in trend by breaking down the science, sharing personal stories and talking risk factors and red flags. Join us for an honest and definitely necessary conversation. 

TIME Magazine by Jamie Ducharme 

Colorectal Cancer Alliance 

In this week's episode, we sit down with author, mother, and fellow podcaster Jessica Fein, whose journey through loss and resilience is deeply meaningful and helpful for anyone going thru it. Jessica has endured the heartbreaking losses of her mother, father, two sisters, and her 17-year-old daughter, Dalia—each shaping her understanding of grief, love, and the strength it takes to keep moving forward.

Her memoir, Breathtaking: A Memoir of Family, Dreams, and Broken Genes, offers a deeply moving look at life with Dalia, who passed away from MERRF syndrome, and explores the depths of loss and resilience. Featured in The New York Times, Newsweek, The Boston Globe, and HuffPost, Jessica’s work sheds light on the power of storytelling and the beauty that can coexist with grief

Despite experiencing unimaginable loss, Jessica walks through the world with all the grace and has made it her mission in finding purpose in pain and connection in sharing her story. We are honored to have connected with her and it's our privilege to be able to  share her wisdom, strength, and perspective with this conversation.Bottom line, even in loss, love endures. 

About Jessica Fein

I Don't Know How You Do It Podcast 

Breath Taking: A Memoir of Family, Dreams and Broken Dreams 

What exactly is MERRF Syndrome? 

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We've always called this time of year the 'dark ages,' and honestly, reality is proving us right—so we’re leaning in. In this week’s episode, we welcome Jill back and catch up on all things 2025. From cities burning to shake-ups in the White House to the never-ending seasonal illnesses (seriously, why won’t they leave?), we cover it all.

Sounds a little bleak? Maybe… but as always, we find reasons to be grateful—like our mom, who got to really flex her 'mom' muscles this month. (Thanks, Mom!) Plus, we’ve got some breaking-but-not-really-breaking news: Friend of the family and the pod, Bianca Roses, is competing on Survivor 48! We can’t wait to watch her outwit, outplay, and outlast.

So join us as we navigate the darkness of winter—and, as always, find the light.

Bianca Roses Pre-Season SURVIVOR Interview 

Meet the Cast of SURVIVOR 48