Skip to content
PodcastsEducationHow Hard Can It Be? with Diana Maria Riva

How Hard Can It Be? with Diana Maria Riva

iHeartPodcasts
How Hard Can It Be? with Diana Maria Riva
Latest episode

32 episodes

  • How Hard Can It Be? with Diana Maria Riva

    Millennials vs. Gen X: Comparing Notes on Midlife with Francia Raisa & Jessica Marie Garcia

    10/08/2026 | 50 mins.
    Host Diana Maria Riva is joined by her millennial babes Francia Raisa (Grown-ish, How I Met Your Father) and Jessica Marie Garcia (Liv and Maddie, On My Block) to swap notes on what midlife really looks like. They talk openly about midlife facts and fiction (night sweats, perimenopause, sex drive), the challenges of finding the right OB-GYN before you need one, and the power of embracing a new chapter in life. Francia, Jessica and Diana also discuss dating and relationships, self-trust, and the one message they have for their future selves.
    See omnystudio.com/listener for privacy information.
  • How Hard Can It Be? with Diana Maria Riva

    Toxic Love, the Sex and the City Paradox, and Dating Right after 50 with Sabrina Bendory

    10/01/2026 | 50 mins.
    Host Diana Maria Riva sits down with relationship coach and bestselling author Sabrina Bendory to talk about finding love, recognizing the difference between chaos and chemistry, and the discovering of our true selves in the process. They get into the different types of toxic behavior (love bombing, mirroring, bread crumbing), how movies, TV shows AND dating apps have skewed our views on what healthy relationships look like, and the myth that it’s too late to find love after 40. Whether you're newly single, dating again after divorce, or 30 years into a marriage, this episode speaks the blunt truth to the standards, or lack thereof, we live by.
    See omnystudio.com/listener for privacy information.
  • How Hard Can It Be? with Diana Maria Riva

    Ashley Jones on the AARP Ambush, Dating Profiles, and Co-Parenting After Divorce

    09/24/2026 | 44 mins.
    Actress Ashley Jones (The Bold and the Beautiful, General Hospital, Beyond the Gates) joins host Diana Maria Riva to talk about recognizing anxiety as a legit symptom of perimenopause, her uninvited notification from the AARP, and how forgiveness and even friendship is possible after divorce. Ashley and Diana also quiz a couple of 30-something’s on what is considered TMI on a first date, ageism in daytime TV, and how day-trading has made her feel more empowered than ever.
    See omnystudio.com/listener for privacy information.
  • How Hard Can It Be? with Diana Maria Riva

    Elisa Donovan on Grief, Saying No, and Rebuilding After Losing it All

    09/17/2026 | 36 mins.
    Actress Elisa Donovan (Clueless,Night at the Roxbury, Sabrina the Teenage Witch) stops by the show and discusses the blow felt when everything you’ve built your identity on disappears at once, the difference between choosing a partner versus a project, and raising a teen with your own father’s voice. Diana and Elisa also discuss the importance of evolving friendships, mastering the art of “I don’t have the bandwidth”, and suddenly changing your mind about marriage.
    See omnystudio.com/listener for privacy information.
  • How Hard Can It Be? with Diana Maria Riva

    Shaun Robinson on Aging Out Loud, the Power of Representation, and Helping the Next Generation

    09/10/2026 | 46 mins.
    Award-winning journalist and 90 Day Fiancé host Shaun Robinson joins the show to talk about the moment she stopped hiding her age and the freedom and relief that came with embracing it. Shaun and Diana also discuss the dangers of AI-perfect influencers, what a body type is even supposed to mean, and why she thinks the universal appeal of 90 Day Fiancé is really about how far people will go to be loved. They also get into how Shaun’s upbringing took her on a life-long journey of philanthropy and helping young women
    See omnystudio.com/listener for privacy information.
More Education podcasts
About How Hard Can It Be? with Diana Maria Riva
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?
Podcast website

Listen to How Hard Can It Be? with Diana Maria Riva, The Jamie Kern Lima Show and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features
How Hard Can It Be? with Diana Maria Riva: Podcasts in Family
  • Podcast The End Of The World with Josh Clark
    The End Of The World with Josh Clark
    Science, Society & Culture, Technology