Best Date Night With Jake Podcasts (2025)

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Minisode: Not Interested in Being Exclusive with Chelsea + Catherine 10:21

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1d ago10:21

10:21

Chelsea and Catherine cover Chelsea’s modern technology woes, and deal with a listener’s Tesla troubles. * Need some advice from Chelsea? Email us at [email protected] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals partic…

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Nick & Night with Nicholas Sparks 58:03

3d ago58:03

58:03

Author Nicholas Sparks (The Notebook) joins Chelsea to talk about why he kept his day job even after a million-dollar book advance, the weirdest places someone’s proposed in front of him, and the everyday stuff that romantic gestures are really made of. Then: A freelance writer wonders if she’ll ever be able to write something for herself instead o…

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W.N.B.A. Star Natasha Cloud Doesn’t Play When It Comes to Love 38:29

4d ago38:29

38:29

Natasha Cloud is a powerhouse. The New York Liberty point guard seems to have it all: a successful W.N.B.A. career, fierce confidence and a loving relationship with her girlfriend and teammate, Isabelle Harrison. On and off the court, Cloud radiates self-assurance and seems to know exactly who she is, but that sense of self was hard-won. In a conve…

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How to Create More Intimacy Through Communication with Nick and Amy McKinlay 35:45

5d ago35:45

35:45

Today, we're talking about how Christian couples can build deeper intimacy by turning awkward silence into simple, safe conversations. Nick and Amy McKinlay of Ultimate Intimacy share research-backed prompts, healthy masculinity traits, and ways to navigate power dynamics when desire is mismatched. • why communication is the core of sexual intimacy…

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I Kissed a Girl, Owning “Lesbian” & Toxic Labels: Georgia Robert 47:12

5d ago47:12

47:12

In this episode, we sit down with Georgia Robert, a standout from I Kissed a Girl Season 1 and semi-pro footballer for a raw, funny and unexpectedly emotional conversation about identity, labels, sport and self-acceptance. 🌈 We get into why the word lesbian felt impossible to say, how school culture shaped shame, and why doing the show flipped ever…

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Twice with Mitch Albom 1:09:12

10d ago1:09:12

1:09:12

Mitch Albom is here to discuss why there will never be a Wednesdays with Morrie, his unexpected path to writing the best-selling memoir of all time, and how the regrets of his past led him to the blessings in his present. Then: A new writer isn’t sure where to start with her memoir. And an established author worries the secrets of her past will cau…

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The Woman Who Can Make Affairs Disappear 31:53

11d ago31:53

31:53

In cities across China, there’s a special kind of consultant you can hire if you find out your spouse is cheating. They’re called “mistress dispellers,” and their job is to work their way into your spouse’s life, get close to their lover and convince the pair to break it off. When all goes according to plan, the cheaters end up believing it was the…

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A Simple Relational Skill That Makes Communication So Much Easier 12:57

12d ago12:57

12:57

What if a single, gentle question could turn tense moments into real connection? That’s the promise of “contracting,” a simple consent-based habit that replaces surprise talks with intentional, focused conversations. We walk through how this tiny shift—asking “Is now a good time?” and agreeing on a short window—respects attention, reduces defensive…

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Conversion Therapy, Dating & Iron Fists: Eman Akwafo 46:07

12d ago46:07

46:07

In this episode, we sit down with actor, writer and producer Eman, whose work and lived experience confronts the intersections of queerness, faith and Black masculinity. From award-nominated stage work (For Black Boys…) to creating his upcoming play Limp Wrist & The Iron Fist, Eman shares the real story behind his art: including assault, silence, c…

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Episode 6: Marriage and Relationships—Hot Takes...Part 1 48:49

14d ago48:49

48:49

In this episode, we’re diving into some hot takes that might ruffle a few feathers—or at least spark some good conversation. Join us as we unpack our real, unfiltered opinions on everything from homeschooling to married life dynamics. We kick things off by sharing our recent journey into homeschooling—what led us there, what surprised us, and why i…

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Minisode: Fighting Back with Mikie Sherrill 22:11

16d ago22:11

22:11

New Jersey Gubernatorial Candidate Mikie Sherrill talks with Chelsea about why the race for governor matters on a national scale, how to put a slimy opponent in their place, and what every American can do to fight back against looming fascism. * Get involved at Mikiesherrill.com. * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail…

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Outta My House with Martha Plimpton 1:03:59

17d ago1:03:59

1:03:59

Martha Plimpton joins Chelsea to talk about leaving her hometown, why abortion rights and trans rights go hand in hand, and the things you learn from young love. Then: A newly-therapized daughter suddenly can’t stand her misogynist dad. A 20-something keeps dating cheaters. And a mom is losing her cool after her MIL moves in. * Abortion Resources -…

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Malala Thought She’d Never Fall in Love 55:53

18d ago55:53

55:53

When she was 15 years old, Malala Yousafzai was shot by the Taliban, targeted for saying that young women should have the right to an education. By the time she woke from the ensuing coma, the world had already cast her in the role of fearless activist. In the years that followed, she embraced the part, starting the Malala Fund and traveling the gl…

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Shoveling Sh*t Together: How Kass and Mike Built Companies, Raised Kids, and Kept Their Marriage Intact 34:29

19d ago34:29

34:29

What if the real love story isn’t candlelight and grand gestures, but calendars, clarity, and courage under pressure? I sit down with Kass and Mike Lazerow—longtime partners in life and business—to unpack how they navigated Web 1.0 startups, gut-punch setbacks, and life-changing, $345 million-dollar exits while raising three kids and staying on the…

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Being invisible, Ghana & Boycotting: Two Twos 51:12

19d ago51:12

51:12

In this episode, we sit down with award-winning podcasters and community icons Nana and Ro, the duo behind Two Twos Podcast, a space that redefined what it means to be Black, British, and queer. 🌈 From humble YouTube beginnings to shaping conversations around identity, masculinity, and representation, the pair open up about five years of laughter, …

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Minisode: International Day of the Girl: Ending Child Marriage 16:35

23d ago16:35

16:35

Princess Mabel of Orange-Nassau talks to Chelsea about why child marriage is still such a prevalent issue in the world - even in the US - and what we can do about it. * You can help! Visit Vow for Girls or Unchained at Last to get involved. Recommended Reading Half the Sky: Turning Oppression into Opportunity for Women Worldwide * Need some advice …

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It’s Me or The Dog with Madelaine Petsch 49:38

24d ago49:38

49:38

Madelaine Petsch joins Chelsea to talk about reconsidering motherhood, her love of horror films, and biting off more than you can chew. Then: A friendship is on the brink after a misunderstanding about the news. A friend wants to help her bestie lose her virginity. And a woman must choose between her boyfriend and her beloved dog. * Need some advic…

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Tessa Thompson on Finding What You Want (What You Really, Really Want) 39:50

25d ago39:50

39:50

Tessa Thompson’s latest role is an infamously chaotic one: Hedda Gabler. Adapted from the classic play by Henrik Ibsen, “Hedda,” in select theaters Oct. 22, casts Thompson as a 1950s housewife who feels snubbed by an old lover and stifled in a new marriage. For Hedda, the only exit strategy is to punish those who have hurt her and then destroy hers…

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Marriage is the Ultimate Team Sport: How to Create a Winning Team 18:57

26d ago18:57

18:57

By Monica Tanner - Marriage and Intimacy Coach for Christian Couples

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Culture, Top Surgery & Egypt: Nxdia 1:10:21

26d ago1:10:21

1:10:21

In this episode, we sit down with artist Nxdia, who opens up about growing up between Cairo and Manchester, navigating identity, and creating music that captures the complexity of queerness, culture, and self-expression. From journaling teenage crushes that inspired viral tracks to processing faith, gender, and belonging, Nxdia shares the stories b…

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Minisode: Nickname for Jupiter with Chelsea + Catherine 16:45

30d ago16:45

16:45

Chelsea and Catherine figure out how to survive AI, and a caller wonders if she should fake an acid trip. * Need some advice from Chelsea? Email us at [email protected] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals parti…

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Dating the Good Dad with Judy Greer 1:05:45

1M ago1:05:45

1:05:45

Judy Greer joins Chelsea to chat about the time she got fired from a movie set, why step-parenting is the clutch job, and why you don’t get weekends off when you date the good dad. Then: An Angeleno realizes she’s accidentally dating a MAGAt. And a young mom struggles in her marriage when her wife’s unemployment seems neverending. * Gratitude Journ…

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For Her 70th Birthday, She Hired an Escort 36:54

1M ago36:54

36:54

Gail Rice, a writer and a therapist, was approaching her 70th birthday. She had given up on dating apps and hadn’t had a romantic connection with anyone in years. But for her 70th, she wanted a very specific birthday present: an orgasm. So Rice decided to hire an escort. In this episode, she describes what went right, what went wrong and what she’s…

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Debunking Bad Marriage Advice with My Son and Daughter-In-Law Jake and Livvy 32:59

1M ago32:59

32:59

Today's interview is with my oldest son, Jake and his new wife, Livvy to chat about the new book I wrote for them and unpack five of the most common myths that sabotage new marriages and trade them for simple habits that build trust, respect and joy. Thinks we talk about in the episode are: • faith first, spouse second as good advice from Livvy's D…

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Autism, Masculinity & Soulla: Alex Theo 53:55

1M ago53:55

53:55

In this episode, Alex opens up about his journey growing up as a Greek Cypriot lad from North London, navigating queerness, comedy, drag, and autism. He shares how his alter-ego “Soulla” was inspired by his mum and supported by his grandma, the struggles and acceptance he’s faced within his Cypriot community, and the powerful messages audiences hav…

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Does This Make Me Funny? With Zosia Mamet 56:47

1M ago56:47

56:47

Zosia Mamet joins Chelsea to talk about surviving an eating disorder, the time Nyquil-induced hallucinations almost got her fired from Girls, and why being a nepito baby isn’t all it’s cracked up to be. Then: A Chicagoan wonders if he should give up his pastime as a comment warrior. And a soon-to-be-groom has reservations about inviting his mother …

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How an Off-Script Moment Changed Jay Duplass’s Life 42:32

1M ago42:32

42:32

Jay Duplass knows the power of improvisation. Many years ago, an unscripted, cliffside interaction changed his life, helping to set in motion the events that would lead to his new movie, “The Baltimorons.” The film features a newly sober comedian and a workaholic dentist who meet on Christmas Eve during an emergency dental procedure. What follows i…

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Debunking Sex Myths in Marriage 14:34

1M ago14:34

14:34

Bad sexual advice is one of the top reasons couples struggle early in marriage, often because most grow up with distorted expectations about what a healthy sex life looks like. • Sex advice is usually messed up because the topic is taboo in most families • Most couples start marriage with distorted expectations about their sex life • "A Good Wife K…

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Attitude Magazine, Real Bodies & Asylum Seekers 33:54

1M ago33:54

33:54

In this solo episode, after being featured in Attitude Magazine, we talk about body image, insecurities, race, hair, weight, and what it’s taken for us to finally love ourselves in a queer community that doesn’t always make that easy. We share the behind-the-scenes of our photoshoot with Gomez, the nerves of stripping down, and the hilarious (and a…

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Minisode: Single White Female with Chelsea + Catherine 17:17

1M ago17:17

17:17

Chelsea and Catherine get a Friends-with-Benefits followup and hear from a mother-daughter-duo who inspire stalkers. * Need some advice from Chelsea? Email us at [email protected] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or indivi…

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I Am Not Your Enemy with Whistleblower Reality Winner 50:09

1M ago50:09

50:09

Chelsea is joined today by whistleblower Reality Winner, a former linguist and intelligence analyst, arrested in 2017 for leaking classified documents about Russian interference in the 2016 election. They discuss Reality’s arrest, incarceration and recovery - and why it’s so important to speak out when you see injustice. * Need some advice from Che…

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You Think You Know Elizabeth Gilbert. You Don’t. 53:43

2M ago53:43

53:43

When her wildly popular memoir “Eat Pray Love” came out in 2006, Elizabeth Gilbert suddenly found herself touted as an expert on self fulfillment, spirituality and love. Readers might assume that Gilbert had vanquished her demons as she settled into a life of fame and marriage to the man she fell in love with at the end of the book. But her struggl…

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Detoxing from Bad Marriage Advice 12:10

2M ago12:10

12:10

A marriage advice detox can transform your relationship by eliminating harmful myths and replacing them with practical communication skills. Bad marriage advice like "never go to bed angry" or "happy wife, happy life" often sounds good but leads to frustration and resentment when applied to real relationships. • Identify the marriage beliefs and ad…

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Episode 5: Late Night Thoughts on a Broken World 50:16

2M ago50:16

50:16

In this late-night episode, we've taken a less formal, more off-the-cuff approach — just Britt and I in conversation, reflecting in real time quite literally in our bed. We open up about the rising tensions we’re seeing in our country — from the recent assassination surrounding Charlie Kirk, a targeted political killing seeking to silence the voice…

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Gay Culture, Stepbrother Fantasies & Comedy Gold: Jake Jonez 1:01:33

2M ago1:01:33

1:01:33

In this episode, we’re joined by Jake Jonez: the unapologetic artist, comedian, and rising pop provocateur shaking up queer culture. From small-town Georgia to viral TikTok skits and bold music videos, Jake’s story is one of defiance, humour and hard-earned self-expression. We dive into growing up gay in the South, channeling anger into art, and wh…

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Jersey Girls with Debbie Gibson 1:00:27

2M ago1:00:27

1:00:27

Debbie Gibson joins Chelsea in-studio to talk about the one that got away, when teenage girls know more than men in suits, and what life is like in her second act. Then: Menopause has a divorcee feeling down. A 30-something and her bestie beef with judgmental parents. And a grieving daughter wants to get her life back. * Need some advice from Chels…

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Why I Always Dreamed of Being a Sister Wife 48:33

2M ago48:33

48:33

Christine Woolley always knew she wanted to be in a plural marriage. She grew up in a fundamentalist Mormon community, loved having two moms and several grandmothers, and wanted to raise her own children in that environment. As an adult, and after Woolley married a man with two other wives, her family decided to share their lives on the TLC show “S…

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Moving From Approval to True Intimacy in Marriage with Dr. Jennifer Finlayson-Fife 42:17

2M ago42:17

42:17

Dr. Jennifer Finlayson-Fife explores how moving beyond validation-seeking creates deeper, more authentic intimate connections in marriage, explaining that true intimacy requires embracing differences rather than demanding constant agreement. • Distinguishing between validation and true intimacy in relationships • Understanding the three unhealthy r…

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Episode 4: Generational Gaps and Growing Up Differently 1:08:28

2M ago1:08:28

1:08:28

In this episode, we dive into the fascinating differences—and surprising similarities—between Gen Z and Millennials when it comes to growing up, chasing dreams, and navigating adulthood. We sit down with Britt's 23-year-old cousin, Amber, (Gen Z) for a real, unfiltered conversation about how each generation views success, career goals, social media…

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Celebrity Hairstyling, The Met Gala & Latino Representation: Cesar Delon Ramirez 49:20

2M ago49:20

49:20

In this episode, Cesar DeLeon Ramirez shares his journey from growing up in a Puerto Rican household and spending his weekends in a hair salon, to becoming one of the most in-demand celebrity hairstylists in the world. He reflects on the fearless ambition that led him from assisting in New York salons to his first big break with Cassie, preparing f…

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Minisode: Perspicacity with Chelsea + Catherine 17:51

2M ago17:51

17:51

Chelsea and Catherine learn about the need for a new vocab segment, a son wants his mom to move in, and an auntie gets caught playing favorites. * Need some advice from Chelsea? Email us at [email protected] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of t…

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I Hate Loud with Sam Morril 1:02:44

2M ago1:02:44

1:02:44

Comic Sam Morril is in the NY studio to discuss the problem with dating younger people, tormenting morning news hosts, and why a rec center is his home away from home. Then: Soon-Yi confusion ensues as a daughter struggles to accept her dad’s romantic escapades. * Need some advice from Chelsea? Email us at [email protected] * Executive P…

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Episode 3: Homesteading—Part 1 53:28

2M ago53:28

53:28

In this episode, we’re discussing our journey into homesteading — the good, the messy, the stings, and the sweet honey in between. What started as a simple idea turned into a life-changing shift as we traded convenience for connection, and chaos for something closer to nature (though let’s be honest, there’s still plenty of chaos — just the feather…

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E. Jean Carroll’s Vibrant Sex Life Ended 30 Years Ago. She Wants It Back. 31:52

2M ago31:52

31:52

When the writer E. Jean Carroll accused President Trump of sexual assault in 2019, she unearthed a memory she had pushed away for decades. She also admitted, for the first time, something she hadn’t fully reckoned with: She hadn’t had sex since. In this episode, Carroll tells Anna Martin what it was like for her to go from “man crazy” to someone wh…

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Incompatibility is the Leading Cause of Divorce AND It's a Myth 13:59

2M ago13:59

13:59

Conflict and differences in marriage don't mean you married the wrong person; they simply mean you're two human beings from different backgrounds working together to build a life. Statistics show "incompatibility" is the leading cause of divorce, but what couples often interpret as irreconcilable differences are actually normal variations in perspe…

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Gay Dating, Misogyny & The Mykonos Policeman: Rossi Lewis 54:37

2M ago54:37

54:37

In this episode, we sit down with Rossi Lewis: storyteller, content creator, and accidental “dating diarist” whose TikTok journey began with a chance meeting at the gym and spiraled into documenting the chaos, comedy, and heartbreak of gay dating. Rossi opens up about his early years in Cardiff, navigating anger, therapy, and the challenges of grow…

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Life on the PTSD List with Kathy Griffin 1:07:06

2M ago1:07:06

1:07:06

The iconic Kathy Griffin joins Chelsea to have a frank talk about facelifts, spontaneous combustion, and the photo that got her canceled. Then: A busy professional is ready to build new relationships after friends’ passing. And a 34-year-old is ready to retire… or maybe marry Kathy? * Need some advice from Chelsea? Email us at DearChelseaPodcast@gm…

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Nic and Olandria on What the ‘Love Island’ Cameras Missed 43:23

2M ago43:23

43:23

Olandria Carthen and Nic Vansteenberghe spent a lot of this past season on “Love Island USA” coupled up with other people, but in a last-minute twist they wound up together. Fans were divided. They read into body language, smirks, eye contact and passing comments to try to piece together whether Nic and Olandria got together out of convenience or t…

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Stop Listening to These 5 Pieces of Common Marriage Advice 19:18

2M ago19:18

19:18

Marriage advice is everywhere, but much of it is outdated, misguided, or flat-out harmful to your relationship, no matter how well-intentioned it may be. • Happy couples don't fight - FALSE: Conflict is like exercise for your relationship and helps you grow stronger • The myth of "don't sweat the small stuff" can lead to an explosion after years of…

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Episode 2: Home is Where He Leads Us. 55:01

2M ago55:01

55:01

In this episode, we open up about the journey that took us from our small hometown of Marshfield, Wisconsin, to Indiana—and to several other locations as well. Leaving the comfort and familiarity of where we grew up wasn’t easy. We faced emotional goodbyes, unexpected challenges, and seasons of uncertainty. But through it all, we began to see how G…