Uptown Dale & Rachel Sobel

Friends Without Benefits

Society EN ↓ 137 episodes

One woman. One man. Thirty plus years of strictly platonic friendship with ZERO romantic history between them. This is Friends Without Benefits. Rachel Sobel is the face behind the popular blog and Instagram account, Whine and Cheez-its. She is the mother of two, a do-over wife, and award-winning writer, author and speaker. Dale McLean is a South Florida entertainment staple affectionately known as Uptown Dale. He is a bachelor, owner of a successful entertainment company, television personality and in-arena host for the Miami Heat. Together they tackle a range of topics around relationships,...

Author

Uptown Dale & Rachel Sobel

Category

Society

Podcast website

whineandcheezits.com

Latest episode

May 26, 2026

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Episodes

S4 Ep. 28 - Baby Jessica Got Arrested and Rachel Got a Book Deal 26.05.2026

Then the headlines come in hot: TSA officers at Miami International got caught stealing wallets mid-screening in a coordinated distraction scheme, a nurse wins $300K from Carnival for being over-served tequila over nine hours on a cruise (14 shots, grown adult, still won), Baby Jessica from the Texas well incident grew up and got arrested for domestic assault, a Boca woman crashed into a school bu...

S4 Ep. 27 - The Boca E-Bike Incident and Dale's Stingy Instagram Grid 19.05.2026

Things kick off with a full breakdown of the e-bike drama taking over Boca. A middle-aged man threw water bottles at a kid, grabbed his phone, and somehow rallied a crowd of neighbors like he put out a bat signal. Rachel and Amy unpack why this guy isn't in handcuffs, what it means for every teen in the community, and why e-bikes in the hands of unsupervised kids are a whole separate problem...

S4 Ep. 26 - The $500 He Never Asked For Back 12.05.2026

Dale has been sitting on a $500 loan for almost a year, has seen the guy in person, and still hasn't said a word. Rachel and Amy Lundy — creator of MOABs, the Mother of All Baby Showers, and today's in-studio guest — talk him into sending a Venmo request like a normal person. He won't. Meanwhile, Rachel's daughter crashes the call-in line, reports on the missing hair dryer, eat...

S4 Ep. 25 - Bring Your Child to Work Day With a Nine Year Old Who Has No Filter 05.05.2026

Rachel's youngest crashes the pod on Bring Your Child to Work Day, and the nine-year-old wastes zero time fact-checking adults, interrupting tangents, and quietly stealing the episode. The trio covers Justin Bieber's Coachella laptop loophole, why he couldn't legally sing his own songs live, and whether Madonna and Sabrina Carpenter's collab was genius or just a little too forc...

S4 Ep. 24 - Red Flags, Crocs, and a Bad Connections 21.04.2026

Rachel posted what she thought was a hilarious reel of her daughter breaking every rule at a dog adoption event — finger in every single cage — and one pointed comment was enough to put a pit in her stomach and make her take it down. Dale gets it. The whole thing spirals into a real conversation about how one contrarian comment can ruin your day even when you know it's just someone looking fo...

S4 Ep. 23 - $100 Hot Dogs and Our First Guest Call Ins 14.04.2026

Dale and Rachel kick things off with some truly questionable food trends, including a $100 hot dog covered in caviar and gold, fair food debates, and a passionate takedown of white chocolate. Somewhere between Biscoff funnel cake cravings and Hot Cheetos dumplings, things go exactly where you’d expect and also nowhere you’d predict. Then they try something new and bring listeners into the show liv...

S4 Ep. 22 - Dale's Germaphobia Gets The Best of Him at E11EVEN in Miami 07.04.2026

Dale and Rachel kick things off with a full in-studio moment featuring their sponsor finally showing up in person, complete with a custom jingle and a little champagne energy to match. What starts as catching up with an old friend turns into a surprisingly honest conversation about personal injury law, billboards, and why people only appreciate lawyers when they actually need one. From there, thin...

S4 Ep. 21 - Why The Bachelorette Was Canceled Last Minute 31.03.2026

Dale and Rachel get right into the chaos around The Bachelorette getting pulled just days before it was supposed to air, and they have a lot of thoughts. From messy casting decisions to whether the network knew more than they let on, they break down how it all unfolded and what could have been done differently. It turns into a bigger conversation about reality TV, accountability, and how far shows...

S4 Ep. 20 - Would You Ever Take a Bath in a Hotel Tub? 24.03.2026

Dale and Rachel start off with a debate that quickly spirals into a full germaphobe confession session. From hotel carpets to shared bathtubs and those mystery shampoo bottles mounted in the shower, they compare their personal travel habits and the lengths they’ll go to avoid other people’s germs. Let’s just say hotel flip flops, towel walkways, and strong opinions about public hygiene all make an...

S4 Ep. 19 - Are Your Quirks Actually OCD 17.03.2026

Dale starts things off with a story about a friendship that abruptly ended after he gave some blunt advice about dating patterns. What he thought was an honest moment between friends quickly escalated into someone deciding the friendship should end altogether, which leads to a conversation about how honesty, tone in text messages, and personal insecurities can completely change how things are rece...

S4 Ep. 18 - The Curious Case of the Disappearing Condoms 10.03.2026

Dale and Rachel start out talking Olympics drama, curling controversy, and the fact that 10,000 condoms disappeared in three days at the Village. But as usual, the jokes lead somewhere deeper. Rachel also shares her first experience at Buc-ee's. The conversation starts with Buc-ee's famous brisket sandwiches and takes a tangent into reality show chaos, and a very real rant about parents...

S4 Ep. 17 - Why We Need To Cancel Valentine’s Day 03.03.2026

Rachel and Dale are not buying the hype when it comes to Valentine’s Day. The whole thing feels like a setup, the pressure is weird, the restaurants are overpriced, and somehow you are still expected to post a perfect little highlight reel like everyone else. From there, they get into the Bad Bunny Super Bowl halftime performance and how the reaction to it says more about people than the show itse...

S4 Ep. 16 - If You Have to Leave a List for Your Husband, That’s a Problem 24.02.2026

A viral video about wives leaving their husbands a checklist for watching their own kids turns into a real conversation about parenting, partnership, and what it actually means to split the load. Rachel is clear. A husband is not a babysitter. If you have to explain how to feed your own child, something is off. They get into gambling with your life for money, car wash price gouging, why some peopl...

S4 Ep. 15 - When Sharing Too Much Goes Sideways 17.02.2026

Rachel and Dale start from a simple question they have lived out for years. They have never crossed the platonic line. That somehow opens the door to everything else. Boundaries that feel blurry. Oversharing that turns private moments into content. Parenting in the age of social media. Period parties. Sonograms online. New slang that makes adults feel old overnight. And the quiet pressure to post...

S4 Ep. 14 - Uncle Dale Reporting for Duty to Parent Rachel's Teenager 10.02.2026

Rachel and Dale are basically walking proof that a long friendship can stay truly platonic, but we still have to ask the obvious question. Is that rare for a reason, or are people just messy with boundaries. We start with real life stuff like parenting a teenager and trying to keep your cool without losing your mind, then we get into the kind of family dynamics that can quietly ruin a relationship...

S4 Ep. 13 - What Is the Right Thermostat Temperature for a Relationship? 03.02.2026

Rachel and Dale start with a very serious debate about air conditioning etiquette and what counts as “acceptable” when it comes to temperature, then spiral into snow angels, South Florida winters, and whether TikTok is ruining everyone’s attention span. Rachel’s daughter joins the chaos with peak teen honesty, including what’s officially cringy, what’s not, and why adults love acting like their er...

S4 Ep. 12 - Reborn Dolls, Rude Servers, and the Weirdest Holiday Conversations 13.01.2026

Rachel and Dale kick off the holiday stretch the way they do best, by spiraling through the strange headlines and the everyday moments that somehow say a lot about people. They start with the story of a woman who faked an entire pregnancy with a reborn doll, then bounce through a service that roasts your boss for you, a revenge spray paint moment that is honestly unforgettable, and why people feel...

S4 Ep. 11 - Whatchu Watchin, Culture Takes, and Unfiltered Opinions 06.01.2026

In this episode of Friends Without Benefits, Dale and Rachel lean all the way into their favorite end of year ritual. A full social media purge, strong opinions about lurkers, and a reminder that social media is meant to be social. From their recurring segment What Are You Watching to deep dives into cult documentaries, celebrity reckoning stories, pop culture chaos, and unexpected takes on Wicked...

S4 Ep. 10 - Can Men and Women Stay Just Friends A Funny Honest Conversation About Platonic Love 30.12.2025

In this episode of Friends Without Benefits, we dig into one big question we get asked all the time. Can men and women really stay just friends? As two longtime friends who have never crossed the platonic line, we share our real life experiences, laugh through listener shoutouts, and talk honestly about friendship, attention, and what it means when people actually miss your podcast during a break....

S4 Ep. 9 - Salmon Sperm Masks, Spirit Airlines, and Platonic Friend Chaos 23.12.2025

Dale and Rachel catch up on life, travel, and the strange conversations that only long-term platonic friends can have. They debate manicures, dating standards, and whether asking for a feet picture is ever acceptable. Rachel explains why she wore a salmon sperm face mask on a flight and how she handled the internet backlash that followed. The conversation shifts to Dale’s NBC6 appearance, the brai...

S4 Ep. 8 - Daylight Saving Debates, Viral Trends, and Thanksgiving Chaos 25.11.2025

In this episode of Friends Without Benefits, Dale and Rachel jump straight into the holiday season with their take on daylight saving time, the chaos of early Christmas displays, and why the whole world is suddenly obsessed with the viral six seven trend. They unpack the slang teens are using now, compare it to the phrases they grew up with, and laugh through the generational gap that gets wider b...

S4 Ep. 7 - From Whatcha Watchin’ to Whatcha Wearing 18.11.2025

Dale and Rachel roll out their new segment Whatcha Watchin’ and dive into their latest TV obsessions—from wild true-crime dramas to addictive reality shows. Then they switch gears to fashion, testing each other on how to actually pronounce those luxury brand names we all fake confidence saying (Hermès, Balmain, Givenchy… or is it “Vasace”?). Toss in a few blind-date stories, some puppy yoga confus...

S4 Ep. 6 - Wedding Cancelled, Party Saved, and Bush Underwear Sold Out 11.11.2025

In this hilarious and unpredictable episode, Dale and Rachel dive into stories you won’t believe are true. From a bride who turned her canceled wedding into a celebration for the homeless, to Miami luxury apartments across from prisons, to Kim Kardashian’s viral “bush underwear” that somehow sold out—nothing is off limits. The duo also swaps their wildest Google searches, debates germ-infested eve...

S4 Ep. 5 - A Belated Halloween Episode: Candy, Camp, and Call Lee 04.11.2025

Rachel and Dale are back for a spirited belated Halloween edition of Friends Without Benefits ! This episode is packed with hilarious stories, nostalgic moments, and a little bit of heart. The duo celebrates their brand-new sponsor (hello, 1-800-CALL-LEE), shares how their camp roots led to lifelong friendships, and dives into the chaos of trunk-or-treats, favorite candies, and the bizarre etiquet...

S4 Ep. 4 - Camp Tales, Plane Snacks, and One Penny Plans 14.10.2025

We are back for season four and we are seasoning it right. We swap stories from our camp days, argue about pulp in orange juice, and expose the absolute no foods for airplanes. We test drive Dale’s one penny idea for good and dream up a donation challenge that actually helps the unhoused. There is a goat in Gucci, a python bounty in Florida, and a quick tour of our new studio. Rachel wraps with a...

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