The Deep Dive with Jessica St. Clair and June Diane Raphael

The Deep Dive with Jessica St. Clair and June Diane Raphael

Each week, comedians and best friends Jessica St. Clair and June Diane Raphael take a ‘deep dive’ into their real lives and discuss a wide range of topics including how to pursue joy amidst the insanity of motherhood and family, grief and loss, sh*t they put on their faces, and why they refuse to check their voicemails or unpack their suitcases. The Deep Dive captures the friendship of two women trying to survive adult womanhood. Their motto, shared by their loyal Deep Divers, is "Let Us Live!"

Episodes

October 4, 2025 33 mins

This week we’re popping in your feed to tell you about a new show from Lemonada Media, Since You Asked

Who doesn’t need advice—and who doesn’t love giving advice? Since you asked, we’re happy to answer. Each week, two friends—Gretchen Rubin, a happiness researcher, and Lori Gottlieb, a therapist—tackle the daily problems of living with all of you. Whether it’s the pet peeve tha...

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Jessica is wearing a girdle, June is communicating via stickers, and our skeletons are in conversation. We also dive into our tap dance legacies and the benefits of TV dinners.

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE. 

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September 24, 2025 47 mins

June is on set, Jess is on drugs, and the first 20 minutes of this episode were never recorded and will never be heard again. Plus we get granular on our friends’ daily schedules, June overhears people having sex (??) in a hotel, and Jess dives into her post-op experience.

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE. 

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September 20, 2025 30 mins

There are a thousand podcasts you can listen to. This one listens back. And this week, we’re here to tell you about it.

Alive with Steve Burns continues the conversation you began all those years ago. Back then it was letters and numbers and graham crackers. Now it’s death, sex, taxes, and all the big, messy questions of being alive. Why does money stress us out? Is the American dream dead? What’s the future of tr...

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September 17, 2025 57 mins

Deep Divers, it’s eclipse season and we want to make sure you have it all together (including your last will and testament). Plus, June falls in love with Burger King, Jessica gives us some French fashion highlights, and we dive into signs from the beyond.

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE. 

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September 10, 2025 59 mins

Jessica is back from her French holiday and gives us a full breakdown on everything from French dog etiquette to how to mime a pool noodle. Plus we chat the heartbreak of school drop-offs, and June professes her newfound love for Stanley cups.

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE. 

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This week, while Jess is out galavanting all of France, June welcomes special guest Elizabeth Laime on the Deep Dive to talk Mahjong betrayals, turning an office into a parlor (for joy, obviously), and surviving a dental cleaning from Dante's Inferno. Plus, we debate gum health, x-ray gag reflexes, and whether dentists are… frauds?

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE.&...

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August 27, 2025 57 mins

June and Jessica chat astrology, hoagies, and the destruction our periods cause. Plus we decide it’s never too late to apologize and sometimes it’s best to just take yourself out of the game.

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE. 

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August 20, 2025 54 mins

June gets pulled into a game of red light, green light and Jess is volume eating Milanos. Plus June witnesses her parents in a new light and we dive into the power of a song. 

Gaza Aid

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August 13, 2025 56 mins

Jessica is taking on a whole new personality and June tells us the origin story of her world-changing “pants-less” look. Then we dive into how we are choosing to share our energy and how to put down an expired relationship.

World Food Program Gaza Donation

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August 6, 2025 57 mins

Summer is still in full-swing and Jessica and June are refusing to cook for breakfast or lunch (and encourage you to do the same). Plus, Paul takes care of our snacks, June gives us a breakdown of her new TV obsession, and we learn St. Clairs don’t go to the movies.

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/DIVE

See omnystudio.com/listener for privacy information.

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July 30, 2025 50 mins

This week, Jessica and June are crying over text messages and receiving urgent voice notes. Plus June is on CapTok, Jessica is working on her shiny red shell, and she acknowledges that she IS, in fact, an actor.

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July 23, 2025 59 mins

This week, June gives credit where credit is due, and Jessica delivers a retraction (plus a retraction on that retraction) regarding eyelashes. Then we chat the Kardashians, who is smacking Jessica’s butt, and June’s terrifying elevator encounter. 

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July 19, 2025 61 mins

This week, we revisit when Jessica and June face their harshest comedy critics - their children. Then they dive into bedroom kids vs. living room kids, the joy of a sectional, Thanksgiving plans, and reality TV drama. And please be advised, Deep Divers: moving forward, we will be adopting mob wife looks and attitudes. Try. Me.

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July 16, 2025 59 mins

In this week’s very spooky episode, Jessica is on the lookout for sharks and June is avoiding crows. Plus we chat big dinosaurs, white on white cars, oral historians, and Jessica and June’s experiences working for the mafia.

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July 9, 2025 57 mins

This week, Jessica’s family curse has finally been broken and June’s family is enforcing a dress code. Plus we dive into theater experiences of our past, ditch the judgment-free zone, and learn that June may be a professional athlete. 

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This week, we are sharing packing tips from two of our most trusted sources: teens and TikTok. Then June fights to remove the stigma around unwashed makeup brushes while Jessica steals from GOOP. Plus, we dive a little deeper into Carolyn Bessette, “Alone,” and Karen Read trial theories.

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June 25, 2025 58 mins

This week we are talking to dead people and trying to understand how anxiety works. Then June confesses some damage she’s done to her body while Jessica is in awe of her own ass. Plus, we learn that what happens in a hospital should probably stay in a hospital, not all three-ways are created equal, and your body may be a tax write-off.

CW: Please note, this episode contains a brief reference to sexual abuse.

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June 18, 2025 53 mins

This week, June is embracing her new life as an online gamer while Jessica is realizing she may have a secret passion for board games after all. Plus, Jessica goes Top Gun on a jet ski, and we reach our limit on travel excursions led by energy vampires.

domesticworkers.org

chirla.org

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June 11, 2025 60 mins

This week, Jessica is giving sex advice to strangers and June has the best day of her life. Plus we talk structured vs. unstructured summers, Star Wars (??), and petty theft from the hotel spa.

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