How Hard Can It Be? with Diana Maria Riva

Episodes

• Happy Hour with Tina: Diana’s Make-Out Era, Dating App Disasters & FaceTime Bar Nights 16.06.2026 8m

  Host Diana Maria Riva and her bestie Tina are back for a happy hour recap of the Constance Marie episode. They discuss why Tina has practically danced with Prince and David Bowie, where women land on the household totem pole and keeping the spark alive in long relationships. The conversation takes a hilarious turn as Diana shares her midlife dating adventures, including swiping through "Bob the Builder" lookalikes and turning down a 32-year-old suitor.See omnystudio.com/listener for privacy information.
• Constance Marie on Midlife Dating, Single Motherhood and What’s a Sesentañera? 11.06.2026 45m

  Actress Constance Marie joins host Diana Maria Riva for a rollercoaster conversation from being last on the list, to single motherhood, and the wild world of dating apps (clean shirts and punctuality, is that too much to ask?!). And what better way to celebrate 60 than with a Sesentañera…A sesenta-WHAT? From disappearing eyebrows and why Gen X women refuse to stop pivoting, Diana and Constance compare notes and dive in deep.See omnystudio.com/listener for privacy information.
• A Midlife Awakening, Not a Crisis, with Wendy Valentine 04.06.2026 38m

  Diana Maria Riva sits down with author and podcast host Wendy Valentine for a conversation about how the scariest moment of your life can actually be the beginning of your best chapter. Wendy shares how hitting rock bottom in her mid 40’s — divorce, debt, depression, and devastating loss — led to a wild vision of driving an RV across the country. Diana and Wendy also talk about the importance of becoming your own BFF, setting boundaries, and why Gen X women are just getting started.Wendy Valentine is the author of Women Waking Up: The Midlife Manifesto for Passion, Purpose, and Play and host of The Midlife Makeover Show.See omnystudio.com/listener for privacy information.
• Happy Hour with Tina: Love, Loss and Laughing Through Midlife 02.06.2026 10m

  Grab that Prosecco, it’s time for a new Happy Hour episode of How Hard Can it Be? This week, host Diana Maria Riva and her bestie Tina reflect on the recent episode with actress Lisa Vidal. Diana and Tina talk about keeping the spark alive after 35 years of marriage, navigating the unimaginable loss of a child and the importance of showing up for friends in their darkest moments. See omnystudio.com/listener for privacy information.
• Lisa Vidal on Surviving Grief, Choosing Joy and Still Being Hot at 60 28.05.2026 44m

  Actress Lisa Vidal sits down with host Diana Maria Riva for a raw, heartfelt conversation about the realities of aging, the beauty of long marriages, and the devastating loss of her son. Lisa opens up about her 36-year marriage, battling breast cancer while being the family breadwinner, and how she chooses healing every single day. Lisa and Diana also laugh through midlife's greatest hits — bingo wings, chin hairs, disappearing eyebrows, and the foreplay of Pinterest. Please note this episode contains discussions of suicide. If you or someone you know is experiencing a mental health crisis or suicidal thoughts, please reach out for immediate help. You can call or text the 988 Suicide & Crisis Lifeline.See omnystudio.com/listener for privacy information.
• Gina Torres On Becoming an Empty Nester: No Carpool, No Minivan, No Identity, NO PROBLEM! 21.05.2026 32m

  Host Diana Maria Riva welcomes actress Gina Torres to talk about the messy, hilarious, and surprisingly emotional journey of becoming an empty nester. From IKEA shelf disasters to red-eye drop-offs, Diana and Gina discuss the importance of rediscovering who you are on the other side of motherhood. All this and a rapid fire game of hot flashes, self-care, and spontaneous sex.See omnystudio.com/listener for privacy information.
• Happy Hour with Tina: Sleep Wars, Parenting & Not Stopping at No 19.05.2026 12m

  It’s time for another bonus Happy Hour episode of How Hard Can it Be? This week, host Diana Maria Riva and her bestie Tina discuss the conversation with Holly Robinson Peete, including their takes on the separate bedrooms trend, menopause sleep struggles, and Holly’s inspiring approach to her son’s autism diagnosis. See omnystudio.com/listener for privacy information.
• Holly Robinson Peete: Never Ever Say Never... A Candid Conversation About Separate Beds, Being Critical, Autism & Midlife Joy 14.05.2026 57m

  Holly Robinson Peete joins Diana Maria Riva for a refreshingly blunt discussion about the lessons, discoveries, and surprises of midlife.  From the joy of separate bedrooms (and a Great Dane named Atlas) to life with an adult child with autism, Holly opens up about defying the long list of “never’s” that came with her son RJ's diagnosis. Diana and Holly engage in a comical conversation full of laughs and moving honesty as Holly shares her journey of “letting go”, the joys of Japan, Instagram shopping, and her 90-year-old mother’s fearless approach to aging. See omnystudio.com/listener for privacy information.
• Happy Hour with Tina: Pivoting, Saying No and Asking “Why Not?" 12.05.2026 9m

  In this special Happy Hour episode of How Hard Can it Be?, host Diana Maria Riva is joined by her best friend of over 40 years, Tina, for a glass of prosecco and a heartfelt chat. They reflect on the Eva Longoria episode and dive into Tina's inspiring pivot — from owning the biggest driving school in Cincinnati's tri-state area to selling the business and opening a spa in her house. They celebrate the power of asking "why not?", the freedom of saying no after 50, and how age can quiet self-doubt. See omnystudio.com/listener for privacy information.
• Eva Longoria on Midlife: GirlSquads, Sleep Secrets, and Saying "No" 07.05.2026 1h

  In the debut episode of How Hard Can it Be?, host Diana Maria Riva sits down with her close friend Eva Longoria - actress, producer, director, activist, and executive producer of this very show - for a no-holds-barred conversation about what it really means to be a Gen X woman navigating midlife. From being the regents of resourcefulness to the indignities of chin hair and gravity, they talk about it all: the company you keep, the power of saying no, why society's "expiration date" for women is total BS, and yes - the optimal timing for sex. Hilarious, honest, and unapologetically real. Take the sleep type test here.See omnystudio.com/listener for privacy information.
• Introducing: How Hard Can It Be? with Diana Maria Riva 30.04.2026 1m

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