That Greenwich Life

By: Dorothy Cascerceri Simone
  • Summary

  • Hi, I’m Dorothy Cascerceri Simone, and I’m taking you on a glamorous ride inside one of the bougiest, over-the-top zip codes in the country where I’m peeling back the layers beyond the lavish, luxurious lifestyle of That Greenwich Life. I’ve spent years as a magazine editor and media personality. I’ve interviewed A-listers like Brad and Angelina and talked celebrity news on just about every major TV network. I’ve worked for People magazine, In Touch Weekly and Life & Style, but these days with a new baby and an 8-year-old, I’ve traded in red carpets for the lacrosse field sidelines of Greenwich CT – but make no mistake my shoe collection is not collecting dust. In a town of Bentleys and Birkin bags – I own neither – I’m not apologizing for wearing Forever 21 with my Fendi. Join me each episode for authentic and unfiltered conversations about the real, raw relatable human experiences we all share whether you have 50 dollars or 50 mill in the bank: We’re ALL struggling with something. Those BIG things in your life you wish you could change - the things that make 2am to 6am the hardest and longest part of the day. For me, it was a years-long trauma-filled fertility journey, but for you maybe it’s finding love, your career, your kids, your aging parents, or your marriage. Together, we’ll search for the best in the worst of times, find joy, peace and purpose in the mess, and transform, heal – and dare I say have loads of fun - as we grow. One thing I’ve learned is no matter how fancy or important you think you are, we are all joined on this journey called life. So let’s talk . About your life, my life. Our life. THAT GREENWICH LIFE. Follow us now on Apple Podcasts, Spotify, or wherever you enjoy your shows.
    2024, That Greenwich Life, All Rights Reserved
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Episodes
  • Ep 32 - Your 2025 Glow-Up Pt 3: Listening To Your Inner Truth + Boundary Work That's Kind To Yourself and Others
    Jan 16 2025

    Welcome to Episode 32 of That Greenwich Life! In this solo episode, Part 3 of our 2025 Glow-Up Series, I’m diving into an essential but often overlooked part of the glow-up journey: learning to listen to yourself, setting boundaries with intention and how it’s possible to communicate those boundaries to others with honesty and kindness.
    This week I’m reflecting on my own experiences and lessons learned—especially around navigating busy seasons, saying "no" when needed, and embracing the power of intentional decisions.
    Using New Year’s Eve as a springboard, I explore how we can move away from people-pleasing, let go of guilt, and prioritize what truly nourishes our souls, while still honestly communicating our boundaries with people in a caring way. This episode is all about creating space for mindfulness, honoring your needs, and making room for what feels right while still being considerate of others.

    In This Episode:
    • Why New Year’s resolutions don’t work—and why setting intentions instead helps take the pressure off
    • The importance of slowing down and tuning into what you and your family truly need
    • Real-life lessons from a busy holiday season and learning to say “no” without guilt
    • Why setting boundaries isn’t selfish—it’s essential for your well-being and your relationships
    • How intentional choices can make space for more meaningful connections in 2025

    Thank You to This Week’s Sponsors:
    I’m so grateful for this episode’s sponsors, whose support makes this podcast possible:
    • Illume Fertility: For anyone on a fertility journey, Illume Fertility provides compassionate, personalized care every step of the way. Their team of specialists understands the emotional and physical challenges that come with infertility and works tirelessly to create a plan tailored just for you. I know firsthand how overwhelming this journey can be, and having a supportive partner like Illume Fertility can make all the difference. Learn more at IllumeFertility.com and @IllumeFertility on Instagram
    • Steam Greenwich: Steam has become a go-to in my home for fresh, homemade dim sum and more. From their authentic noodles and rice dishes to their famous soup dumplings – which my picky eaters in my house love! - every bite is perfection. What I love most is their commitment to the Greenwich community—they’ve created a welcoming spot where even middle and high school students can grab an affordable meal after school and feel at home. Give yourself a break from cooking and order takeout, delivery, or dine in today at SteamGreenwich.com and @SteamGreenwich on Instagram.

    Stay Connected:
    Follow me on Instagram at @DorothyOnTV, shop That Greenwich Life merch at DorothyOnTV.com, and watch this episode on YouTube at DorothyTV.
    If you loved this episode, please rate, review, and share it with a friend who could use a little inspiration for their own 2025 glow-up. Remember, don’t just live your life—love it!

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    39 mins
  • Ep 31 - Your 2025 Glow-Up Pt 2: The Skincare and Leveling Up Mindset You Need This Year
    Jan 9 2025

    Welcome to Episode 31 of That Greenwich Life! As we continue our 2025 Glow-Up Series, in Part 2, I’m thrilled to dive into a topic that’s more than skin-deep—skincare as self-care. This week, I’m joined by Nicole Caroline, a master esthetician with over 25 years of experience, a celebrity clientele, and a brand-new luxury spa right here on Greenwich Avenue, Nicole Caroline Skin.
    Together, we explore how caring for your skin can transform your confidence and even your soul.
    We talk all about overcoming that annoying self-doubt we all experience from time to time and the importance of pausing to really soak in pinnacle moments. She’s not just about glowing skin—she’s about glowing from within, and her story will leave you inspired to take bold steps in your own life.
    We also talk practical skincare tips, like the importance of a nighttime double cleanse – cleansing with oil of all things! - to remove makeup and sunscreen, and the magic of her signature ice spheres for depuffing, glowing skin, and even calming your nervous system. Nicole’s philosophy is simple but powerful: when you feel good in your skin, it shows in every part of your life.

    Featured in This Episode:
    • Why authenticity and uniqueness is your “signature sauce”
    • How skincare became a healing ritual for Dorothy during difficult times of pregnancy loss, miscarriage and failed IVF.
    • The connection between self-care, confidence, and building a thriving business or leveling up in any place of your life.
    • Simple ways to upgrade your skincare routine, no matter your budget or schedule.

    Thank You to This Week’s Sponsors:

    • Room For Paws Pet Resort: Keeping our fur babies happy while we juggle busy schedules. Check out their puppy preschool to get your pup behaving the way you want him/her to. Learn more at RoomForPawsPetResort.com.
    • Steam Greenwich: Because everyone deserves a night off from cooking. Order fresh, authentic dim sum, noodles, chicken, beef and shrimp dishes and more at SteamGreenwich.com.

    Stay Connected:
    Follow me on Instagram: @DorothyOnTV, shop That Greenwich Life merch at the shop tab at DorothyOnTV.com, and catch this episode (and more) on my YouTube channel, @DorothyOnTV.
    If you loved this episode, please leave a review, share it with your friends, and let’s glow up together in 2025!

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    43 mins
  • Ep 30 - Your 2025 Glow-Up Pt 1: The Travel You Need To Book This Year
    Jan 2 2025

    It’s the 30th episode of That Greenwich Life and the first of 2025! I can’t believe how far we’ve come, and I’m so excited to kick off the year with a super fun special episode with tons of travel ideas as part of That Greenwich Life’s 5-part 2025 Glow-Up series this month.
    No New Year’s Resolutions here because – let’s be honest – who really keeps them? I know I don’t. Instead of only hitting the gym hardcore with the rest of the pack (ok…we can do that also), I’m focusing on five areas of our lives where we could all use just a little bit more self-care, attention and direction.
    This week in Part 1, I’m joined by my longtime friend and incredible NYC-based travel journalist, Juliet Izon, whose work has been featured in The New York Times, Travel + Leisure, The Wall Street Journal and more. Together – since you all know by now I’m a travel writer as well! - we’re sharing travel ideas and tips for every season and school break, whether you're dreaming of a spring getaway, summer escape, or a holiday trip to end the year. From Grenada to Morocco, Norway to San Diego, there’s something here for everyone, no matter your style or budget.
    What’s Inside:
    • February Break Inspiration: Grenada’s serene Silver Sands Beach House and my upcoming trip to Beaches Turks & Caicos (with a magical stop at the Wizarding World of Harry Potter on the way back to Greenwich!).
    • Spring Break Favorites: Morocco and Southern Spain for culture and adventure, or Mallorca for a quieter, off-season vibe.
    • Summer Escapes: Norway’s fjords and culinary treasures, or a surprising pick—Vail, Colorado—perfect for hiking and llama treks.
    • Holiday Travel Magic: Juliet shares her wintertime Lake Placid experience at Lake Placid Lodge, while I talk about the incredible Hotel del Coronado in San Diego.

    Special Thanks: PodPopuli for hosting me and to this episode’s sponsors, Illume Fertility and Steam Greenwich.
    llume Fertility is a leading fertility and family-building practice serving the tri-state area since 2002, led by an award-winning team of highly credentialed, board-certified reproductive endocrinologists. I wish I knew about them when I was going through my grueling IVF journey. Visit IllumeFertility.com for more info.
    Steam on Greenwich Avenue is your perfect solution for taking the night off from cooking. Visit www.SteamGreenwich.com for authentic dishes like dim sum, noodles, rice, duck and more – and enjoy a meal that’s fresh, homemade and that the whole family will love.
    Don’t Forget to Shop the Merch!
    Kick off 2025 in style with That Greenwich Life merch—hoodies, mugs, and more! Perfect for locals or anyone who loves the show. Visit the shop tab at DorothyOnTV.com.
    Let’s Stay Connected:
    • Follow Juliet: Instagram: @julietizon | Website: julietizon.com
    • Follow Me: Instagram: @DorothyOnTV | Website: DorothyOnTV.com
    • Watch the show: Youtube.com/@DorothyOnTV
    Thanks for listening! Don’t forget to subscribe, leave a review, and start booking your next adventure. Tune in the next five weeks for more of my 2025 Glow-Up series, and remember:
    Don’t just live your life—love it! ?

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    45 mins

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