That Greenwich Life
That Greenwich Life
Dorothy Cascerceri Simone
Hi, I'm Dorothy, a reformed celebrity gossip girl and mom of two living That Greenwich Life in the suburb of Greenwich, Connecticut. Once upon a time, I was a red carpet reporter and tabloid magazine editor in New York City, appearing on all your favorite TV shows spilling the secrets of the stars. But now, I'm using my storytelling power for a purpose far greater than gossip. My own traumatic journey to motherhood and late-stage pregnancy loss taught me that we're all dealing with hard stuff. And it's that shared experience that bonds us together more than we realize.You don't need to live in Greenwich or even locate it on a map to join me every Thursday. All you need is a love for stories that are real, raw, and remind us just how resilient and connected we all really are. Now let's get started.
Ep 8, Season 2: When Life Changes the Plan: Navigating Uncertainty and Redefining Giftedness with Special Guest Julie Vincent
 Some seasons don’t just stretch you — they quietly change how you see your life, your health, and the future you thought you were moving toward. And it can happen in an instant when one piece of news changes everything. The hardest part may seem like the moment you receive the news, but the long stretch of not knowing that follows can be even harder: the endless appointments, the unanswered questions, and the quiet fear that hums beneath the surface while life keeps moving forward . You’re still parenting, working, showing up, and trying to stay hopeful… even when everything feels uncertain.On this episode of That Greenwich Life, we’re talking about what happens when life hands you something you never planned for — and how you find your footing again when the ground underneath you shifts. My guest, Julie Vincent — @IamJulieVincent on Instagram - is a mother, advocate, and the founder of The Gifted Life — who shares her deeply personal journey of navigating her daughter’s rare genetic diagnosis - followed by her own – and the years of uncertainty and the emotional toll of living in the in-between. Through her story, we explore how answers, even when they’re hard, can become a turning point — and how choosing presence, truth, and self-trust can change everything. It’s a conversation about optimism over panic, truth over denial, and learning how to live fully — right where you are.Thank You to Our Sponsors: • RMA of New York — our Season 2 Presenting Sponsor and leading fertility care provider • Jack Rabbits Gymnastics and Soccer Club — a beloved children’s movement and enrichment space helping kids build confidence, coordination, and joy through play • Room for Paws Pet Resort — a trusted, full-service pet resort providing exceptional care and peace of mind for families and their furry family membersLet’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel. 
Jan 19
1 hr 2 min
Ep 7, Season 2: Soul Contracts + Breaking Cycles of Generational Trauma with special guest shamanic healer Eve Kerwin, the White Buffalo Woman
Last week on That Greenwich Life, we opened a conversation so many of us have been carrying quietly for years — the shame, confusion, and emotional exhaustion of family estrangement.And the messages that poured in made one thing unmistakably clear: you are not alone.So in this episode, we’re continuing that conversation — and going deeper - because estrangement doesn’t usually begin with one explosive moment, one argument, or one final breaking point. It often begins inside toxic family systems — patterns we were born into, roles we never chose, and cycles that stretch back farther than any of us realize.In this episode, we explore generational trauma, and to help us unpack all of this, I’m joined by Eve Kerwin, also known as The White Buffalo Woman — a shamanic healer I found in the middle of one of the darkest seasons of my life. In a single session, she helped me make sense of my past, offered clarity around profound loss, and gently opened my eyes to what might still be possible in my future (which she SO ACCURATELY PREDICTED!) — when hope felt completely out of reach.Eve Kerwin has worked with clients around the world for decades, guiding them through grief, trauma, ancestral patterns, and spiritual awakening. Drawing from intuitive healing, soul work, and Akashic wisdom, Eve offers a deeply compassionate lens on why we experience the relationships and challenges we do — and how healing can ripple far beyond one lifetime.Thank You to Our Sponsors: • RMA of New York — our Season 2 Presenting Sponsor and leading fertility care provider • Jack Rabbits Gymnastics and Soccer Club — a beloved children’s movement and enrichment space helping kids build confidence, coordination, and joy through play • Room for Paws Pet Resort — a trusted, full-service pet resort providing exceptional care and peace of mind for families and their furry family membersLet’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my 
Jan 12
1 hr 3 min
Ep 6, Season 2: The People We Grieve Who Are Still Alive - A Deep Dive into Estrangement with special guest Bianca Jade
Listener Note: This episode includes discussion of suicidal ideations. There are some conversations we avoid because they’re heavy and complicated - and because they bring up shame, grief, and questions that don’t have easy answers.This episode is one of those conversations. But I’m not avoiding it any longer.This week on That Greenwich Life, we’re opening the door to a topic so many people are living with quietly: family estrangement. Not the dramatic version people assume — but the slow, painful unraveling that happens when relationships meant to feel safe begin to feel harmful, draining, or deeply confusing. And this can also apply to friends who feel like family – or at least used to.My guest this week, Bianca Jade - @BiancaJade on Instagram -- is a TV host, content creator, and leading beauty, health, and lifestyle influencer who has openly shared her infertility journey and path to motherhood with a level of vulnerability and authenticity that has helped countless women, men, and families—including me personally. She has appeared on major outlets including the Today Show, CBS Morning News, Dr. Oz, and regional affiliates across the country.If you’ve ever felt torn between loyalty and self-protection…If you’ve ever questioned your own reality because “they’re family”…If you’ve ever carried grief for a relationship that never became what you hoped it would or one that went from feeling safe and familiar to unsafe and unfamiliar…this episode is for you. Thank You to Our Sponsors: • RMA of New York — our Presenting Sponsor and leading fertility care provider • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for! Let’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel. 
Jan 5
1 hr 19 min
Ep 5, Season 2: Reinvention, Identity Shifts + Finding What’s Next — with special guest Sharon Macey
 This week’s episode is for every woman who has ever looked at her life — the career, the home, the relationships, the routines — and quietly wondered:How did I get here… and what do I actually want next?We’re diving into the subtle identity shifts that happen over time — the ones we don’t always see coming. The ones that show up after motherhood, after loss, after burnout, after you’ve held everyone else together for so long that you suddenly realize:I don’t feel connected to myself anymore - and I want more.And in this episode, I’m sitting down with someone who understands reinvention in a way that feels both comforting and electrifying: Sharon Macey — host of the podcast “Mom To More,”  who has devoted her work to helping women return to themselves and figure out their next chapter.Together, we explore:the quiet ways women lose their sense of identitythe “stuck” feeling that so many of us try to push awaywhat reinvention actually looks like — in real time, not the polished versionThis conversation is grounding and honest and full of those moments where you suddenly feel less alone — the kind that remind you your second act doesn’t have to look like your first.You are allowed to want more, and you are allowed to discover parts of yourself you haven’t met yet.This episode feels like exhaling — and maybe even like the very beginning of your next chapter.Thank You to Our Sponsors: • RMA of New York — our Presenting Sponsor and leading fertility care provider • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for! Let’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel. Until next week - don’t just live your life, LOVE it!
Dec 22, 2025
1 hr 3 min
Ep 4, Season 2: Why Some Female Friendships Feel So Complicated — And What You Can Do About It with special guest Julia Dzafic of Lemon Stripes
This episode opens the door to a conversation so many of you have been whispering about, DM’ing me about, and trying to navigate quietly on your own:how female friendships shift in midlife and especially in motherhood — and why it feels so confusing.If you’ve ever found yourself wondering why you don’t talk to your friends the way you used to,why coordinating even a 15-minute coffee feels impossible,why some relationships feel stronger than ever while others suddenly feel misaligned,this episode is going to feel like a deep exhale.I’m joined by creator, author, and mom-of-two Julia Dzafic aka @lemonstripes whose honest conversations about motherhood, mental health, and the messy and beautiful behind-the-scenes of life resonate with so many women. Together, we unpack not just how friendships change as life piles on — but why they do.We talk about the shrinking bandwidth every mom feels, the guilt that creeps in when you’re stretched too thin, and how to tell the difference between a friendship that needs nurturing - and one that has quietly run its course.Make sure you listen to the full episode because toward the end, we also get a special cameo from licensed therapist, author and my best friend, Alison Seponara aka @Theanxietyhealer who you have seen on the show before. She shares her clinical take on why so many women experience this shift, what friendship “misalignment” really means, and how to navigate the emotional layers of these transitions with more clarity and compassion.It’s honest, validating, and the conversation we all need.Thank You to Our Sponsors: • RMA of New York — our Presenting Sponsor and leading fertility care provider • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for! Let’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel. Until next week - don’t just live your life, LOVE it!
Dec 15, 2025
1 hr 2 min
Ep 3, Season 2: The Untold Mental Toll of Perimenopause — And Why You’re Not Imagining a Thing - with special guest, author Lauren Tetenbaum
This episode opens the door to a conversation so many women have been craving: the mental and emotional side of perimenopause — the part no one prepared us for.If you’ve been waking up at 3am, feeling overstimulated, forgetting words mid-sentence, wondering why you don’t quite feel like yourself anymore —  this episode is going to feel like a deep breath.I’m joined by therapist and author Lauren Tetenbaum, whose new book Millennial Menopause is helping women understand what’s happening in their minds and bodies during this transition. Together we unpack not just the physical symptoms we were never taught about — but the emotional toll that comes with it and how important it is for women to pay attention to their mental health at this time of life.We also talk about why so many women feel dismissed by doctors, what real support should look like, and how to advocate for yourself during this chapter of life.It’s validating, eye-opening, and incredibly grounding.It’s an episode you don’t want to miss.Thank You to Our Sponsors and Partners • RMA of New York — our Presenting Sponsor and leading fertility care provider • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for! Let’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. Watch this full episode on my Youtube Channel. Until next week - don’t just live your life, LOVE it!
Dec 8, 2025
58 min
Ep 2, Season 2: Why The Things That Stretch and Scare Us Help Us Grow The Most
This episode pulls back the curtain on the night so many of you followed, supported, and helped bring to life: That Greenwich Life Live at the Hyatt Regency Greenwich.If you’ve ever taken on something that stretched you, scared you, or demanded a fuller version of yourself — this episode will feel familiar in all the best ways.It’s about the honest emotional journey so many of us face behind creating something new: the excitement, the fear, the vulnerability, the imposter syndrome, the gratitude, and the surprising lessons that surfaced along the way.From raising a GRAND TOTAL of $15,600 for Pencils of Promise (YES!!!), to the sea of sequins and sparkle — this episode is a reflection on what happens when a group of like-hearted women gather with intention.I’m also recapping all the exciting things that happened between the end of Season 1 last spring and now. It’s an episode you don’t want to miss! Thank You to Our Sponsors and PartnersRMA of New York — our presenting sponsor, leading fertility care providerHyatt Regency Greenwich Pencils of Promise - our philanthropic partnerGreenwich Lifestyle Magazine — our media partnerVals Putnam Wines & Liquors — our beverage partnerXplorearth — redefining adventure and luxury travelGreenwich Medical Spa — women-owned wellness & skincareSarah Stone Higgins Forbes Global Properties — luxury real estateRoom for Paws Pet Resort Kara Water Constantino’s of Greenwich Thank You Also to Our Travel PartnersThe Wanderer - Kennebunk, MaineThe Hilton Tulum Riviera Maya - Tulum, MexicoPestana Blue Alvor Beach - The Algarve, PortugalExcellence Punta Cana - Dominican RepublicThe Grove Resort - Orlando, FLLet’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. Watch this full episode on my Youtube Channel. Until next week - don’t just live your life, LOVE it!
Dec 1, 2025
1 hr 8 min
Ep 1, Season 2: A LIVE Podcast Experience of Growth + Resilience with special guest Dr. Lucky Sekhon
This very special FIRST episode of Season 2 of That Greenwich Life presented by RMANY was recorded LIVE just a few days ago at the Hyatt Regency Greenwich, where an incredible room full of women gathered for an evening of community, conversation, and purpose. Thanks to the generosity in the room, we raised $13,700 and counting for Pencils of Promise, helping expand access to education for children around the world.The evening began with an elevated cocktail reception with The DJ Tys on the turntables, signature cocktails “The TGL” and “RMANY’s Seed of Hope” , passed hors d’oeuvres, a hot pink step and repeat with a lot of kisses, hugs, laughs and flashbulbs happening in front of it - and the evening all culminated in what you hear in this episode. There were amazing brands with all the latest wellness services and products around the room, a cotton candy machine, disco ball vases full of pink roses, gift bags overflowing with incredible products and the kind of main character energy that is contagious.I took the stage to discuss how change really begins the moment you decide to show up differently, sharing some of my personal challenges—like infertility and loss—and how they’ve shaped my perspective on resilience, empathy, and growth. I reflected on the power of gratitude and how embracing authenticity can ripple out to impact everyone around us. Then a special guest joined: Dr. Lucky Sekhon — a double board-certified reproductive endocrinologist and infertility specialist and OB-GYN at RMA of New York, on-air expert, and advocate for women. She shared amazing insights on reinvention, identity, aging, fertility, burnout, and the mental load. Her book, The Lucky Egg, drops Jan 13 - preorder it now! Whether you were cheering in the audience or you are listening now from home, this episode will leave you feeling empowered, grounded, and seen.Thank You to Our Sponsors and PartnersRMA of New York — our presenting sponsor, leading fertility care providerHyatt Regency Greenwich — host of our live eventPencils of Promise  Greenwich Lifestyle Magazine — our media partnerVals Putnam Wines & Liquors — our beverage partnerXplorearth — redefining adventure and luxury travelGreenwich Medical Spa — women-owned wellness & skincareSarah Stone Higgins Forbes Global Properties — luxury real estateRoom for Paws Pet Resort — luxury, cage-free retreat for petsKara Water — clean, mineral-rich alkaline water systemLet’s Connect!If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. Watch this full episode on my Youtube Channel. Until next week - don’t just live your life, LOVE it!
Nov 24, 2025
59 min
Ep 44, Season 1: Wrapping Up Season 1, the Power of the Pause and the Importance of Living In a Mindset of "We'll See"
     Welcome to Episode 44 of That Greenwich Life! This episode marks the final episode of Season One, and I’m taking a moment to reflect on the incredible journey this podcast has been.When I launched this show last year, I had no idea what it would become—how many people it would positively impact, how deeply personal it would get, and how much it would push me to grow. Over the past year, I’ve shared my own stories and the stories of my incredible guests about motherhood, grief, career pivots, personal reinvention, and all the messy, beautiful, complicated moments in between.     But as I always say on this show, we have to listen to what’s right for us. And right now, I know it’s time to pause, reset, and make space for what’s next.     In this episode, I’m sharing:•        Why I’m taking a break—and why pausing is sometimes the most powerful decision.•        How stepping away from something can help us grow in new ways—personally, creatively, and professionally.•        What’s next? I may not have all the answers, but I’m embracing the “we’ll see” mindset.      Thank You to This Season’s Sponsors:I am beyond grateful to the sponsors who made this season possible. Your support has meant everything! Thank you to Xplorearth and all of my past sponsors, including Party Host Helpers,  Illume Fertility, Steam Greenwich, The Big Picture Art, Jonathan’s Travels, Room for Paws Pet Resort, Jauja Pet , Naomi Fisher at Wellness Insights and more—your belief in this show has been incredible. Special thanks to Podpopuli for having me every week in your Greenwich, CT studio.     Stay Connected:Even though the podcast is taking a pause, I’m not going anywhere! Stay connected with me:•        Instagram: @DorothyOnTV•        Website & Merch: DorothyOnTV.com•        Past Episodes: All episodes will remain available on Apple Podcasts & Spotify, so revisit your favorites anytime!     If this show has meant something to you, please leave a review, share an episode with a friend, and know that this is not goodbye—it’s just a “see you soon.”Thank you for being part of this journey. And remember—don’t just live your life, love it!
Apr 10, 2025
34 min
Ep 43, Season 1: Don’t Wait for ‘Someday’ To Take That Bucket List Trip — How to Make an African Safari Happen with Special Guest Harsh Patil
     Welcome to Episode 43 of That Greenwich Life! If you’re looking for travel inspo for your next vacation, this episode is for you. Most of you know I’ve been a travel writer for over a decade, and if I had a dollar for every person who has asked me through the years, “What’s the best trip you’ve ever taken?” or “What trip should everyone take at least once in their lifetime?,” I’d have my own private jet big enough to fit each and every one of you.      This week I’m joined by Harsh Patil, the CEO and founder of Xplorearth, a luxury travel company specializing in bucket-list experiences, to talk more about my answer to both of those questions time and again – African safaris!  Harsh shares his deep knowledge of this experience and why you don’t need to wait until “someday” to go.     We cover everything you need to know—when to go, how to plan, what to expect, and why safaris are so much more accessible than people think (yes, even for families with kids!). Plus, Harsh shares his insider travel tips and some of the other incredible, off-the-beaten-path adventures he curates around the world.In This Episode:•        The best time of year to go on safari (hint: it’s more flexible than you think!).•        How to plan a family-friendly safari and why it’s an incredible experience for kids.•        Harsh’s insider travel recommendations•        Why your travel dollars matter—how luxury safaris contribute to conservation and support local communities.     A huge thank-you to our amazing sponsors for making this episode possible:     Xplorearth: The go-to travel company for luxury, adventure, and bucket-list experiences. Whether you’re planning an African safari, a Galapagos expedition, or a bespoke wine tour, Xplorearth curates unforgettable journeys. Follow on Instagram @xplorearthwithus for expert travel recommendations. Visit Xplorearth.us and text “Greenwich10” to 732-266-0224 for 10 percent off your trip booked in 2025 for travel in 2025 and 2026.     Room for Paws Pet Resort: Whether you need a safe place for your pup while traveling or expert obedience training, Room for Paws in Stamford, CT provides exceptional care. Learn more at RoomForPawsPetResort.com. Learn more at RoomForPawsPetResort.com.    Podpopuli: The incredible team behind the production of That Greenwich Life! Visit Podpopuli.com to learn more.     Stay Connected:      Follow me on Instagram at @DorothyOnTV, shop That Greenwich Life merch at DorothyOnTV.com, and watch this episode on my Youtube channel.      If you loved this episode, please leave a review, share it with a fellow travel lover, and start planning that dream trip. And remember—don’t just live your life, love it!
Apr 3, 2025
54 min
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