• Kim Fields on Defying the Narrative, Purpose and Preventative Maintenance
    Jun 18 2026

    The iconic Kim Fields joins host Diana Maria Riva for a raw and joyful conversation about what it really means to be a Gen X woman still in motion. Kim shares how she's avoided becoming a statistic, and the moment she realized she was "Burr in a world full of Hamiltons." They talk body image, the trap of comparison, giving yourself permission to look back, and why she's tired of the BS — but never tired of the work.

    See omnystudio.com/listener for privacy information.

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    34 Min.
  • Happy Hour with Tina: Diana’s Make-Out Era, Dating App Disasters & FaceTime Bar Nights
    Jun 16 2026

    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.

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    9 Min.
  • Constance Marie on Midlife Dating, Single Motherhood and What’s a Sesentañera?
    Jun 11 2026

    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.

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    45 Min.
  • A Midlife Awakening, Not a Crisis, with Wendy Valentine
    Jun 4 2026

    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.

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    39 Min.
  • Happy Hour with Tina: Love, Loss and Laughing Through Midlife
    Jun 2 2026

    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.

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    11 Min.
  • Lisa Vidal on Surviving Grief, Choosing Joy and Still Being Hot at 60
    May 28 2026

    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.

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    45 Min.
  • Gina Torres On Becoming an Empty Nester: No Carpool, No Minivan, No Identity, NO PROBLEM!
    May 21 2026

    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.

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    32 Min.
  • Happy Hour with Tina: Sleep Wars, Parenting & Not Stopping at No
    May 19 2026

    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.

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    13 Min.