Uptown Dale & Rachel Sobel
Friends Without Benefits
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
Podcast website
Latest episode
May 26, 2026
Where to listen?
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Episodes
Ep. 36: Do couples who display their relationship on social media owe us answers when they break up? 24.01.2023 31:25
You’ve seen it a million times. The couples who share every single moment of their life on social media – the flowers, the date nights, the gifts, the flu shot check-ins. If they are sharing every second of their courtship or marriage and then they break up, do they owe everyone an explanation? Dale and Rachel are talking all about the phenomenon of super public relationships and what comes along...
Ep. 35: Getting flown out, frozen iguanas and more dating chat 17.01.2023 30:09
Apparently, there are people who get “flown out” for “companionship” and Rachel had no idea. Dale is shedding some light on the unspoken etiquette of being flown out and blows Rachel’s mind. We’re also talking about how Floridians handle a cold front as frozen iguanas fall from the trees, and getting more dating fodder. You can follow Rachel, award winning author, writer and speaker, on Instagra...
Ep. 34: Why Rachel Looks Unhinged When She Travels 10.01.2023 31:48
After a little holiday banter – Christmas trees, menorahs and the whole shebang, Rachel and Dale discuss what kind of travelers they are? Who’s immediately scanning the seat pocket in front of them for a puke bag? Who’s causing stress putting their luggage in the overhead? Which one of them is a psychopath who enjoys the turbulence? And we’re also talking all about the notorious Mile High Club....
Ep. 33: We’re Talking Old Wives Tales 03.01.2023 29:58
Ice in your flowers keeps them alive longer? Ears ringing means someone/s talking about you? Knuckle cracking causing arthritis? Is matzo ball soup really Jewish penicillin? Dale and Rachel are discussing all of the old wives tales they’ve heard throughout their lives and seeing if there’s any truth to them. You can follow Rachel, award winning author, writer and speaker, on Instagram at @whineand...
Ep. 32: Dale and Rachel Are Your Life Coaches Now. First Episode of Ask FWOB! 27.12.2022 30:04
Welcome to, “Ask FWOB”, a new segment of the Pod where we answer your questions! Rachel will ask for submissions regularly in her Instagram stories and then she and Dale tackle your challenges. On this episode we’re talking family boundaries, breaking pregnancy news to a partner who may not be into it, dating for love vs. money and more! You can follow Rachel, award winning author, writer and spea...
Ep. 31: Dale is Going to Date All The Single Moms on Hinge 23.12.2022 34:19
We’re getting an update on Dale’s Hinge experience and learning that he might actually have a type. Watch out single moms! It’s a deep dive into the art of the hinge profile and we’re even going to get into the tea on a couple of his dates. And clearly single moms like Dale right back because they’re willing to drive VERY far to meetup. You can follow Rachel, award winning author, writer and speak...
Ep. 30: Every Woman is a Social Media Sleuth 14.12.2022 32:09
Everyone has that one female friend who becomes a powerhouse social media sleuth when necessary. You know it’s true. The one that deep dives into instagram, public records, ex’s Facebook page. They know what they’re doing. We’re talking all about that today as well as Big Brother, Twitter, Kayne and Adam Levine. A lot of tangents today. You can follow Rachel, award winning author, writer and spe...
Ep. 29: Going Back in Time to Give Advice to Our College Selves 07.12.2022 30:59
In the spirit of hindsight, Rachel and Dale are going back in time to discuss what they would tell their college selves. Highlights include abusing gas cards, over tweezing eyebrows, cargo pants, Mardi Gras and body count. We are all over the map on this one as we stroll down a very interesting and relatable memory lane. You can follow Rachel, award winning author, writer and speaker, on Instag...
Ep. 28: That Time Dale Put His Dating Life in Rachel’s Hands with Hinge! 30.11.2022 27:42
IT’S HAPPENING!!!!! On a previous episode of FWOB, Dale finally agreed to let Rachel create his Hinge profile to dip his toe into the waters of online dating. That’s right! Dale, basically South Florida bachelor royalty, has never ever tried online dating…until now. Rachel had carte blanche to set up Dale’s profile and presented him with the keys to the next chapter of his dating adventures. The...
Ep. 27: When your friend’s significant other sucks, and couples who fight in public 22.11.2022 26:35
This episode is all about couples. Have you ever been in a situation where you can’t stand your friend’s significant other? Do you say something? Do you fake it? All we know is that it’s a slippery slope and Dale and Rachel have feelings about it. Speaking of couples, we’re also talking today about couples who fight in public. The ones who do not hold back from airing their dirty laundry right the...
Ep. 26: Miami Heat Culture, Hurricane Chaos and An Update on Dale’s Date 15.11.2022 27:36
Today we are back behind the mics after dodging Hurricane Nicole here in Florida. This time at Blue Martini Fort Lauderdale. We are digging into Miami Heat Culture and why people in the expensive seats stroll in during halftime. We’re also going to address the elephant in the room - Dale’s date with Taylor from our last set of episodes. We’ve had so many people asking for an update, so get comfor...
Ep. 25: Bachelorettes and Divorcees 26.10.2022 27:30
And to end this bundle of episodes recorded at American Social, we are going out with a bang! It’s bachelorette versus divorcee. Catherine vs. Edna. Two completely different times in two women’s lives converging right here on the FWOB pod. One is wearing a veil and getting ready for her upcoming nuptials, and one is coming out of a marriage and probably burning that veil on the way out (because ch...
Ep. 24: She Met Her Husband After He Ditched His Girlfriend at Her Sister’s Wedding – A Marriage Story 18.10.2022 26:09
We have the pleasure of chatting with our very first married couple on the pod tonight. But they’re not your average married couple. We don’t know what spidey senses Dale is harnessing, but he spotted them at the bar and next thing we knew, they were set up with headphones and mics and we were in for the ride of our lives. Karen first met Tim while he was dressed like a baller in a tux…fresh off o...
Ep. 23:Corner Booth Therapy and Dale is Mistaken for a Famous Athlete 11.10.2022 29:35
Tonight, it’s just the two of us. We’re working through a ton of listener submissions we collected in our little corner booth at American Social. Reading them, dissecting them and analyzing turns into what we’re calling Corner Booth Therapy. We are loving hearing all of the different opinions about whether or not men and women can be friends. And since our pod is built on the foundation of this no...
Ep. 22: Rachel and Dale Might Become Part of a Pro Wrestler’s Entourage 04.10.2022 29:35
We have a man on the pod today who embodies the word hustle. Radio host, TV producer, comedian and soon to be pro wrestler. Oh, and he’s also an Emmy Award Winner. NBD. Fer Rojas is a man of many talents and tonight we’re walking through his journey including what landed him in the ring. We’re also talking about tattoo ideas and his thoughts on couples who have sex in public places. Or as Dale app...
Ep. 21: She’s a 10 AND She’s Danced on Stages with Daddy Yankee, Pitbull and John Legend 28.09.2022 32:49
Dale opens up about his distaste for animal print, which also happens to be a staple in Rachel’s wardrobe. And we have such a special guest today, amazing human, Jenny Valdes (@theejennyvaldes on IG). Jenny is the poster child for living your dream as she poured herself into becoming a professional dancer who has shared the stage with artists like, Pitbull, Daddy Yankee and John Legend. She also...
Ep. 20: Prenups, Dog moms, Vabbing, Destination Weddings, and Strip Clubs 20.09.2022 30:57
While Dale is a walking trend barometer, every now and then, Rachel is able to stump him with something he has never heard of. When she told him that there is a whole movement of women who are apparently engaging in a crazy trend called, vabbing, she really did him in. He was so disgusted he was almost ready to walk of the podcast and become a recluse. Just kidding, but he was shook and repulsed....
Ep. 19: Can you use a gift card on a first date?? 13.09.2022 27:40
Imagine you are a successful entrepreneur; except you do not own a computer or even an iPad and conduct all business through an AOL account circa 1995. That’s Dale and Rachel is trying desperately to usher him into the 21 st Century. In this episode, Rachel and Dale skip the guests and get into the nitty gritty on eating a meal before a night out, red lipstick, eyelash extensions, which bottled...
Ep. 18: Life Updates and Dale is Going on a Date!! 06.09.2022 28:45
We are back at American Social for another crazy night and getting caught up on each other’s lives. Our favorite server, Taylor pops in for a little life update which leads to Dale making plans for a date!!!!! Where will he go? Will she wear sandals? Will there be food to share? We are so excited and can’t wait for the update. You can follow Rachel on Instagram at @whineandcheezits and Dale at @...
Ep.17: That Time Rachel Thought Dale Was Throwing a Swingers Party 31.08.2022 29:28
We are doing a deep dive into Dale’s famous birthday extravaganzas, including Dale’s most recent one which Rachel thought might be a swinger’s theme (Dale loves a theme) because it was at a venue called the Carousel Club. After decades worth of parties, Rachel is breaking down how they usually go and even has help from special guest, Carolina!! You can follow Rachel on Instagram at @whineandche...
Ep.16: Two Single Girls Walk Into A Podcast 23.08.2022 24:56
This is the episode that made Rachel sweat as she helped referee a battle of the sexes between Dale and two single girls who were out on the town. By far the most heated debate on the pod but that’s what you get when you discuss dating in South Florida I suppose. Rachel is finally recovering from playing mediator and staunchly defending Dale’s Ralph Lauren sweater. Join us on this roller coaster o...
Ep. 15: An Update on Dale’s Throuple, Bad Drivers and Some Florida Sports Rivalry Talk 16.08.2022 26:33
We are getting a long-awaited update on Dale’s throuple drama and Rachel asks if he might need to join witness protection over it. We are also joined by owner of @CanesWear, Ken Graff and talk Canes, Gators and Seminoles as well as ranting about bad drivers. There’s a lot of variety in this episode and Dale proves he would make a great hype man as he pumps Rachel up in Episode 15 of Friends Withou...
Ep. 14: Someone who went on real life dates with Dale SPILLS THE TEA! 09.08.2022 29:00
Rachel has been waiting for a moment like this ever since she and Dale discussed starting this podcast. Sitting right across the table is a girl who went on dates in real life with post-pandemic Dale. She’s answering all of the questions and giving a birds eye view into what it’s like to spend time with Dale, including all of his dating quirks. Did he let her share food? Did she break his no flip-...
Ep. 13:One of us has no shame in bringing snacks to the movie theater 02.08.2022 30:23
Who knew that movie theater snacks could be so polarizing? Rachel will never get over the shock of Dale revealing his favorite snack choices. Ever. The duo gets into a spirited debate about movie theater fare and etiquette. And they are joined by Dale’s summer work bestie, Mike (@mikechanan on IG and creator of YouTube’s Freddy Bakes), who breaks down what would have made a viable snack trade for...
Ep. 12: We’re on the chicken finger tour! 26.07.2022 28:51
Ok not really, but we are kind of on a live tour, recording the next several episodes from American Social Las Olas! We’re eating, drinking, talking to patrons and even pulling some of them to be guests. On our first on-location episode, we spontaneously pull in the lovely Taylor. She’s a server at AmSo, studying neuroscience and she’s able to deal with Dale’s humor and give it right back, so she’...
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