How Hard Can It Be? with Diana Maria Riva cover art

How Hard Can It Be? with Diana Maria Riva

How Hard Can It Be? with Diana Maria Riva

By: iHeartPodcasts
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Summary

Diana Maria Riva hosts the weekly podcast for GenX women navigating midlife’s most fantastic bullsh*t. Through laughs, tears, or tears and laughter, Diana invites her squads from Ohio to Hollywood for some real talk on being the boss, the empty nester and the caretaker, all while battling night sweats AND being the linchpins of society. From the FUPA to the hot flash, it's time for women to have unpolished, unfiltered conversations about the midlife roller coaster. With all the changes, surprises and WTFs, join Diana and celebrity guests, experts, and allies as they tackle everything in the second act of life, love, sex and society, as we ask… How hard can it be?

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Episodes
  • Holly Robinson Peete: Never Ever Say Never... A Candid Conversation About Separate Beds, Being Critical, Autism & Midlife Joy

    Holly Robinson Peete: Never Ever Say Never... A Candid Conversation About Separate Beds, Being Critical, Autism & Midlife Joy
    May 14 2026

    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.
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    57 mins
  • Happy Hour with Tina: Pivoting, Saying No and Asking “Why Not?"

    Happy Hour with Tina: Pivoting, Saying No and Asking “Why Not?"
    May 12 2026

    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.
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    10 mins
  • Eva Longoria on Midlife: GirlSquads, Sleep Secrets, and Saying "No"

    Eva Longoria on Midlife: GirlSquads, Sleep Secrets, and Saying "No"
    May 7 2026

    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.
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    1 hr
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