Best Uptown Dale Podcasts (2025)

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S3 Ep. 32 - Doorbell Drama, Hospital Hustles & Exes As Brand Names: A FWOB Finale 33:21

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8d ago33:21

33:21

It’s the season three sendoff you didn’t know you needed. Rachel and Dale bring the laughs and the truth bombs as they dive into parenting teens who definitely lie, why Ring doorbell footage is better than reality TV, and what happens when hospitals start acting like used car lots. (Spoiler: it involves bargaining for surgery like it’s a Black Frid…

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S3 Ep. 31 - No Hookups, Just Hysteria: Foot Pics, Florida Headlines & Why Nice Guys Win 31:52

15d ago31:52

31:52

Rachel and Dale may be “Friends Without Benefits,” but that doesn’t stop them from getting way too real. In this episode, they tackle everything from their unshakable platonic bond to raunchy prank calls, foot pic hustles, dirty restaurant obsessions, and why you should ditch the Justin and marry the Benny. Things get weird (in the best way) with O…

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S3 Ep. 30 - Tow Trucks, Fajita Fakery, And Feral Parenting: Rachel & Dale Unleashed 35:30

22d ago35:30

35:30

Buckle up for one of the most unhinged and hilarious episodes yet! Rachel and Dale go all-in on everything from neighborhood drama (ever towed a booty call’s car?) to fajita fraud (yes, Chili’s fakes the sizzle), and the art of going full “feral mom” when kids get out of line. Nothing—and no one—is safe. They tackle pajama-wearing teens, overpriced…

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S3 Ep. 29 - Never Had Yogurt, Crashed A Wedding, And Almost Fought A Motorcycle: The Season 3 Send-Off You Didn't Know You Needed 35:35

29d ago35:35

35:35

Rachel and Dale close out Friends Without Benefits Season 3 with a bang—and a whole lot of side-eyes. Dale confesses he’s lived an entire adult life without ever trying yogurt (cue Rachel’s existential crisis), while Rachel unloads on the trend of charging guests hundreds to attend weddings (yep, $333 per head). From wild birthday party rules (don’…

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S3 Ep. 28 - Gift Cards, Granola & Gender Reveals Gone Wild: Inside The Most Chaotic Couch Conversation Ever 38:50

1M ago38:50

38:50

Welcome to the wild world of Friends Without Benefits, where besties Rachel and Dale take you on a hilarious, no-holds-barred ride through the absurdity of everyday life. In this episode, Dale tries yogurt for the first time (cue shock), Rachel drops a $27 billion truth bomb about forgotten gift cards, and things spiral into pheromone perfumes, cha…

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S3 Ep. 27 - Soul Checks, Side Boob & The Glitter Trap Dating Hack You Didn’t See Coming 37:46

2M ago37:46

37:46

Rachel and Dale are back and more unfiltered than ever—tackling viral headlines, personal pet peeves, and a game that puts Rachel’s cultural knowledge to the ultimate test. From Tracy Morgan’s courtside meltdown to glitter traps—because apparently, catching a cheater now comes with sparkle. Plus, we dive into breast milk flavored ice cream (it’s a …

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S3 Ep. 26 - Speakerphone, Side Pieces & Survivor Secrets: Confessions Get Wild! 40:37

2M ago40:37

40:37

What starts as a fun round of listener confessions quickly spirals into total chaos—think secret swinging, in-law hookups, gym etiquette wars, and one very disturbing use of a turkey baster. But the real plot twist? Dale’s double life is exposed live on air when his “other podcast partner” walks through the door in a surprise reveal that Rachel orc…

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S3 Ep. 25 - Dale’s Dollars, Haunted Southern Charm & Surprise Nipple Confessions 31:51

2M ago31:51

31:51

We will never not dance to our intro music, and honestly, this episode brings the same energy. Rachel and Dale are back—live from a $7M mansion in Lauderdale-by-the-Sea (shoutout to Courtney Ortiz and her Big Dock Energy). We kick things off with Dale’s latest passion project: Dale’s Dollars, a brilliantly chaotic plan to end poverty one dollar at …

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S3 Ep. 24 - Husbands Who Ghost On Work Trips, Cauliflower Crimes, And The Worst Wedding Toast Ever 37:05

2M ago37:05

37:05

Buckle up, because this episode is a wild ride! Rachel gets fired up about radio silent husbands on work trips (cheating? probably.), the great cauliflower conspiracy (STOP turning it into pizza!), and why cat people are a little… off. Meanwhile, Dale faces the hard truth that he’s been “breadcrumbing” women his whole dating life. 😬 We also unpack …

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S3 Ep. 23 - Elvis, Diddy, And Wedding Drama — PLUS The Secret Life Of A Bar Mitzvah Legend! 31:42

3M ago31:42

31:42

Buckle up, because this episode is a wild ride you didn't know you needed! We're coming to you live (well, kinda) from Sea Ranch Lakes, where Dale gets recognized yet again — because apparently, you can’t walk five feet without someone asking if he does bar mitzvahs (spoiler: he does... a LOT). We dive deep into jaw-dropping celebrity scandals — fr…

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S3 Ep. 22 - Hot Takes & Wild Debates: First-Class, Facials, & Kanye’s Latest Chaos! 32:13

3M ago32:13

32:13

What’s actually worth the hype? We’re diving into a hilarious game of Overrated or Underrated—and trust us, no topic is off-limits! From first-class flights to massages, facials, TSA Pre-Check, and even flying private, we’ve got some strong opinions (and maybe a few unpopular ones). But that’s not all—we’re also talking Kanye & Bianca (is this the …

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S3 Ep. 21 - Fajitas, Football, & Forbidden Secrets – The Internet Can’t Handle Us! 34:39

3M ago34:39

34:39

We’re back, and we’re causing chaos—again! Dale’s very strong opinions on group fajita orders have officially ignited a social media war (even Chili’s got involved). Should you have to ask permission before ordering the sizzling dish of doom? The results may shock you. Then, we break down the most controversial Super Bowl halftime show in years—was…

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S3 Ep. 20 - Fajita Fails & Tinder Ships: The Debates You Didn’t Know You Needed! 33:30

4M ago33:30

33:30

Step inside an exclusive luxury home in Bermuda Riviera with us, thanks to the amazing Courtney Ortiz and One Sotheby’s. We’re talking waterfront views, dream-worthy boat docks, and why you need to see homes in person before making a move. But that’s just the start—things get heated when we debate the ultimate dinner-table betrayal: ordering sizzli…

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S3 Ep. 19 - Boots, Barbies, & Big Dock Energy 38:29

4M ago38:29

38:29

Get ready for a hilarious, unfiltered episode of Friends Without Benefits as we dive into fashion faux pas, Fort Lauderdale luxury, and fiery debates! Uptown Dale embraces his inner Ken while Jeanine defends her equestrian-chic boots—sparking an unexpected debate about polo, sex appeal, and footwear politics. Meanwhile, our “Fairy Podmother” Courtn…

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S3 Ep. 18 - Blind Dates, Prison Brides & Jerry Springer: The Wild Ride Of Reality TV & Real Life 33:32

4M ago33:32

33:32

From Updating’s blindfolded dating chaos to Prison Brides and the jaw-dropping truth behind The Jerry Springer Show, this episode is a rollercoaster of reality TV, nostalgia, and unfiltered laughs. We deep-dive into the psychology of women falling for inmates, debate the best (and worst) Girl Scout cookies, and revisit the outrageous moments that m…

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S3 Ep. 17 - TikTok Meltdowns, YouTuber Drama, And Clublix 38:34

4M ago38:34

38:34

This week, we’re taking you on a hilarious and heartfelt ride through the chaos of modern life. From teenagers freaking out over TikTok’s sudden disappearance to the unbelievable YouTuber adoption scandal that left us outraged, we’re diving into the stories you’ll be thinking about long after you hit play. We also discovered Florida’s Supermarket S…

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S3 Ep. 16 - Listener Confessions, Million Dollar Bananas, And Body Count 32:00

5M ago32:00

32:00

This episode of Friends Without Benefits dives headfirst into life’s quirkiest moments with Rachel and Dale leading the charge. They share hilarious listener confessions, from awkward encounters at weddings to navigating secret relationships and even the bizarre concept of a “listening affair.” The duo also highlights the exclusivity of Sea Ranch L…

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S3 Ep. 15 - Cookies, Yachts, And Podcast Glory: Kicking Off 2025 In Style! 31:55

5M ago31:55

31:55

What better way to welcome 2025 than with fresh cookies, waterfront vibes, and a little podcasting victory dance? We're spilling the tea on how we climbed into the top 10% of global podcasts, sharing hilarious memories from water parks of the past, and debating the holiday reach-out texts that leave us scratching our heads. From decorating debates …

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S3 Ep. 14 - Holiday Cheer, Meme Flirting, and Mariah's Millions 31:43

5M ago31:43

31:43

It’s the holiday season, and Rachel and Dale are back with a festive, witty episode of Friends Without Benefits—this time featuring waterfront views, 71-degree weather, and plenty of holiday hilarity. In this episode, they tackle: Mariah Carey’s Christmas Empire: What The Queen of Christmas rakes in every year from “All I Want for Christmas Is You.…

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S3 Ep. 13 - Push Presents, Candlelight Concerts, and Social Media Shenanigans 35:15

5M ago35:15

35:15

Rachel and Dale are back, bringing their signature wit and unfiltered banter to the latest episode of Friends Without Benefits! This week, the duo dives into: Dale’s hilariously awkward dating saga featuring over-texting, third-date candlelight concerts, and post-date plot twists. The wild world of "push presents"—including Pookie’s $53K Birkin bag…

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S3 Ep. 12 - From Bars To Boats: It's A Podcast GlowUp 29:52

6M ago29:52

29:52

What a journey it’s been—from recording in bars with unexpected swinger encounters to lounging in a $14.5 million mansion on the water. In this laugh-out-loud episode, we reflect on how far we’ve come while tackling your wildest Instagram polls and confessions. Should you tell someone their partner’s cheating? How often do you really change your to…

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S3 Ep. 11 - Over-Texted And Underwhelmed: Navigating Modern Dating Disasters 35:58

6M ago35:58

35:58

Dating in the digital age is messy, hilarious, and sometimes downright awkward—and this episode of Friends Without Benefits delivers all the juicy details. Dale’s dating life takes center stage as he wrestles with an overzealous texter who’s sending his ick meter into overdrive. Rachel chimes in with her trademark wit, dissecting everything from ho…

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S3 Ep. 10 - Worst Jobs, Salacious Songs And Hustle Culture 41:03

7M ago41:03

41:03

Broadcasting from a breathtaking $14.5M estate at 821 Solar Isle Drive, we bring you an episode full of luxury and laughs. As we soak in the setting (and the Big Dock Energy), we swap hilarious tales of our most ridiculous past jobs (ever been a mannequin or a coffin scare actor?), reflect on quirky habits, and debate the best and most “cancel-wort…

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S3 Ep. 9 - Dale Is A Swiftie Now 35:08

7M ago35:08

35:08

In this episode of “Friends Without Benefits,” Rachel and Dale are coming at you from a jaw-dropping $14 million mansion in Fort Lauderdale, courtesy of Courtney Ortiz from One Sotheby’s. Dale gives a blow-by-blow of his unforgettable experience at the Taylor Swift concert, where he navigated Swiftie traditions like trading friendship bracelets and…

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S3 Ep. 8 - Confessions, Fashion Fails, And Sleep Divorces 41:23

7M ago41:23

41:23

In this episode, Rachel and Dale serve up a mix of hilarious confessions and surprising revelations. From Rachel’s change of heart about trendy tiny mics to Dale’s fashion crisis over Travis Scott sneakers, they get real about how opinions can shift. The duo dives into unconventional marriages, asking if living in separate homes can actually work, …

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S3 Ep. 7 - Strip Club Biz, Diddy, and Beyonce Conspiracies 30:52

8M ago30:52

30:52

Rachel and Dale bring the laughs as they dive into the bizarre world of business meetings in strip clubs—because who doesn’t love a little multitasking with their lunch? From debating the hygiene of strip club buffets to questioning the sanity of spending $65 on chicken fingers, this episode is packed with witty banter and outrageous hot takes. But…

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S3 Ep. 6 - Living Large, Laughing Hard Inside Luxury Homes & Mormon Myths 35:17

8M ago35:17

35:17

Rachel and Dale are back, and this time they're recording from a jaw-dropping $5 million home! From master bedroom "waiting rooms" to plush shower seating, they explore the luxury lifestyle with their signature humor and charm. As always, the banter is sharp, with pop culture shout-outs, playful jabs, and Rachel's obsession with incorporating “Jenn…

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S3 Ep. 5 - Miami Fame And Pumpkin Spice Disdain 34:06

8M ago34:06

34:06

In this jam-packed episode of Friends Without Benefits, Dale shares the hilarious behind-the-scenes story of a surprise proposal at a Miami Hurricanes game that went viral for all the right reasons. Listen in as Rachel and Dale dish out our honest opinions on the pumpkin spice frenzy (spoiler: we’re not all fans) and dive into the chaos of our rece…

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S3 Ep. 4 - From NLE Choppa To CucumberTok 38:42

8M ago38:42

38:42

Join Rachel and Dale in this laugh-out-loud episode of Friends Without Benefits as they serve up a mix of outrageous stories, concert chaos, and quirky internet trends. From ASL interpreters signing X-rated rap lyrics to CucumberTok, it's a wide range of topics These two friends are here to share the ridiculousness, along with Rachel’s misadventure…

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S3 Ep. 3 - Google Translate Dating, Testing Dale's Lady Knowledge and Nick Cannon's Insured Bits 35:07

8M ago35:07

35:07

Join Rachel and Dale as they serve up laughs and unexpected twists in this episode of Friends Without Benefits! Ever wondered what it’s like to navigate a first date entirely through Google Translate? You’re in for a treat! Rachel and Dale also dive into hilarious territory as they test Dale's knowledge of tampons, beauty tips, and birth control in…

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S3 Ep. 2 - Summer Shenanigans: LASIK, Bikini Contests, and Frat House Flashbacks 31:07

9M ago31:07

31:07

This episode of Friends Without Benefits is packed with everything from eye surgery adventures to revisiting the wild world of fraternity row. Join Rachel and Dale as they navigate their summer filled with unexpected LASIK surprises, bikini contest hosting, and luxurious real estate daydreams in sunny Pompano Beach. Along the way, they dive into th…

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S3 Ep. 1 - Dale in Drag For His Birthday...Again 38:51

9M ago38:51

38:51

Season 3 of Friends Without Benefits kicks off with Rachel and Dale sharing all the juicy details from Dale's unforgettable birthday bash! From drag queen transformations to wild dance floor antics, they dive into the evolution of Dale’s parties and the hilarious moments that made this year’s celebration one for the books. Rachel reflects on being …

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S2 Ep. 20 - Paranormal Pals, Pina Coladas and Only Fans 38:22

11M ago38:22

38:22

In this episode of Friends Without Benefits, we're getting eerie. Join us as we explore the mysteries of the afterlife with personal ghost stories and debates on the existence of spirits among us. Ever wondered about the authenticity of psychics? We share our skepticism and fascination with the world of tarot readings and psychic mediums, including…

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S2 Ep. 19 - Camaraderie, Inside Jokes and Bikini Contests 35:54

11M ago35:54

35:54

In this episode, you'll hear from Rachel and Dale, as they reminisce about the wild moments, the inside jokes, and the unbeatable camaraderie that makes their friendship truly special. We'll also take you on a virtual tour of our recording haven, courtesy of Fidelity Real Estate, where the ambiance is as inviting as the conversation. Whether you're…

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S2 Ep. 18 - The Ashley Madison Debate 33:42

12M ago33:42

33:42

Rachel and Dale tackle the provocative topic of Ashley Madison, the infamous platform for extramarital affairs, delving into the ethical and emotional fallout of infidelity in the digital age. They debate whether such sites are merely symptoms of deeper relationship issues or active facilitators of deceit. With humor and candor, they explore the ab…

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S2 Ep. 17 - Summer Vibes and Random Thoughts 38:32

12M ago38:32

38:32

Get ready to dive into all things summer, laughter, and a touch of controversy. Whether it's tales of dumb criminals, Bridgerton music, or the latest social media trends, we guarantee a fun and engaging ride. So, grab your favorite drink, tune in, and let us bring some summer sass to your day! Contact Rachel Sobel: Email: [email protected]…

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S2 Ep. 16 - Interracial Dating, Megan Knees, Sleep Divorce and Ozempic 36:24

1y ago36:24

36:24

Today we have Nicole with us to talk about interracial dating and what her personal experience has been like. We're also chatting about random topics like, Megan Thee Stallion’s "Megan knees", sleep divorce, the confusion about Hailey Bieber’s dad, body image and the Ozempic phenomenon. Tune in to "Friends Without Benefits" for a perfect blend of h…

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S2 Ep. 15 - Dale's Dating Adventures Part 129378 46:04

1y ago46:04

46:04

There is never a dull moment in Dale's dating life and Rachel loves to dissect it. The drama is always excellent - chef's kiss. Enjoy this lighthearted episode about everyday life with a dash of introspection. Contact Rachel Sobel: Email: [email protected] Website: www.whineandcheezits.com Facebook: Whine and Cheez - its by Rachel Sobel I…

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S2 Ep. 14 - Dale is Getting Vulnerable Today 35:24

1y ago35:24

35:24

This is a little bit of a different episode for Rachel and Dale. Since many of us have aging parents, Dale is getting vulnerable about his own experience right now with his own mother. So, today, they are peeling back the curtain on a topic close to their hearts: the nuanced dance of family dynamics as parents age. This episode is a tapestry of per…

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S2 Ep. 13 - Tom Brady Roast, Taylor Swift's Explicit Era, And Being Charitable 37:05

1y ago37:05

37:05

Welcome back to Friends Without Benefits! In this episode, Rachel and Dale reunite in a stunning Fort Lauderdale mansion (628 Coral Way to be exact), sponsored by Courtney Ortiz from Fidelity Real Estate. Join them as they dive into the hilariously cringe-worthy Tom Brady roast on Netflix, exploring the best and worst moments. They discuss the surp…

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S2 Ep. 12: The "Babygirl" Vibe, Savannah Bananas and TikTok Trends 30:16

1y ago30:16

30:16

Our latest episode covers a lot of ground! From the evolving landscape of masculinity, exploring the "baby girl vibe" trend to our love for the Harlem Globetrotters of Baseball - The Savannah Bananas, we have a lot to say as usual. Sit back, relax, and join Rachel and Dale for another weekly download sesh on lifestyle topics, TikTok trends, human b…

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S2 Ep. 11: Online antics, Canceled Celebrities and TikTok Scandals 41:16

1y ago41:16

41:16

Join us for our latest episode, where we dive into the absurdities of everything that happens online. Laugh along as we share tales of podcast stardom in Dubai all while questioning why we're not cool enough for those glamorous press trips. From dating blunders to the marriage prospects of conjoined twins, we serve up a buffet of bizarre topics wit…

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S2 Ep. 10: Reality TV Tea and We Play a Few Rounds of FMK 36:34

1y ago36:34

36:34

Today on Friends Without Benefits we dive into our monthly reality TV's recap with all the juiciest tea and behind-the-scenes drama. Then, get ready for some armchair psychoanalysis as we unravel the love triangles and redemption arcs of our favorite reality stars. Brace yourself for a hilarious game of "Eff, Marry, Kill" with TV's biggest names. W…

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S2 Ep. 9: Platonic Bonds, Snowbird Exodus and The Drake Concert Incident 34:07

1y ago34:07

34:07

Ever found yourself in the friend zone and wondered if that was the best place to be? Join Rachel and me, Dale, as we laugh our way through the nuances of platonic friendships and the benefits they bring to our lives in "Friends Without Benefits." We'll take you behind the scenes of our unbreakable bond, share the highs of hosting for the Miami Hea…

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S2 Ep. 8: Opulent Estates, Age Gap Relationships and Biscoff Cookie Obsessions 38:34

1y ago38:34

38:34

Have you ever been mistaken for a celebrity? Well, we spark a hilarious debate about who we apparently mirror in the world of fame and fortune. We also dig into age-gap relationships, inspired by the scrutiny surrounding Kristin Cavallari's love life. We're ripping apart double standards and pondering emotional maturity, all while Rachel cannot rel…

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S2 Ep. 7: From Hair Woes to Fashion Shows and the Tastiest Charcuterie Challenges 29:27

1y ago29:27

29:27

Join us for a hilarious hair-raising adventure as we delve into Dale's people-pleasing habits related to his barbers. This comedic chapter promises laughs as we attempt to untangle the chaos of his styling escapades. We also delve into the high-stakes world of celebrity publicists and what they must have to endure. From DJ Khaled's sneaker branding…

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S2 Ep. 6: All Things Sports with Special Guest, Former NFL Player Donte Whitner 36:51

1y ago36:51

36:51

In our conversation, Donte shares the highs and lows of his draft day, the camaraderie of team dynamics, and the rivalries that fuel competition. We discuss the importance of tone and voice in commanding a presence, whether on the field or behind the mic, and Donte reflects on his 11-year NFL career with the Buffalo Bills, San Francisco 49ers, and …

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S2 Ep. 5: Laughing at Life's Curveballs, Celebrity Encounters and Love is Blind 45:18

1y ago45:18

45:18

Imagine a lifelong friendship filled with laughter, nostalgia, and the occasional microphone mishap. That's the camaraderie Rachel and Dale bring to our latest banter-packed episode. We start with our shared dreams of mansion living, sharing quirky choices for our hypothetical homes. The conversation takes memorable detours through snowy rendezvous…

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S2 Ep. 4: Public personas, Vanderpump and Social Media Etiquette 40:08

1y ago40:08

40:08

Still holding court in a beautiful mansion in Harbor Beach talking about hip hop, more reality TV. We can't not dive into the drama of "Vanderpump Rules" and navigate the stormy waters of on-screen romance and cultural trends, public personas and accountability. We wrap up with a candid chat about social media etiquette and the contradictory nature…

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S2 Ep. 3: Guest Brittany Brave Adds Her Take On Reality TV 39:26

1+ y ago39:26

39:26

Brittany Brave is back for another episode while we take over the gorgeous mansion at 74 Isla Bahia in Fort Lauderdale. Of course there is no shortage of humor as we dive into our obsession with reality TV, from 'Naked Attraction' antics to 'Jersey Shore' charm. We ponder whether reality TV simplifies love or complicates the plot and wrap up with B…