• Maria Hinojosa on the Importance of Independence in a Marriage, Asking Your Kids for Forgiveness, and Being a ‘Wisdom Elder'
    Oct 15 2026

    Pulitzer Prize-Winning Journalist Maria Hinojosa joins Diana Maria Riva to discuss how she’s managed to keep her identity, the secret to her 35-year marriage, and asking her kids for forgiveness for the time her work kept her away from them. Maria also talks about rebuilding in this stage of life, her self-care routine (boxing at 6am?!), and why being called an “elder” won’t slow her down.

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    46 mins
  • Millennials vs. Gen X: Comparing Notes on Midlife with Francia Raisa & Jessica Marie Garcia
    Oct 8 2026

    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.

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    51 mins
  • Toxic Love, the Sex and the City Paradox, and Dating Right after 50 with Sabrina Bendory
    Oct 1 2026

    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.

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    50 mins
  • Ashley Jones on the AARP Ambush, Dating Profiles, and Co-Parenting After Divorce
    Sep 24 2026

    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.

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    44 mins
  • Elisa Donovan on Grief, Saying No, and Rebuilding After Losing it All
    Sep 17 2026

    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.

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    37 mins
  • Shaun Robinson on Aging Out Loud, the Power of Representation, and Helping the Next Generation
    Sep 10 2026

    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

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    46 mins
  • Happy Hour with Tina: Midlife Opportunities, Forget the Clock, and Why Won’t Our Kids Just Live With us Forever?!
    Sep 8 2026

    Grab your drink of choice because it’s time for another Happy Hour episode of How Hard Can it Be? This week, Diana and her bestie Tina recap the conversation with legendary media exec Bonnie Hammer and their main takeaways: stop obsessing over running out of time, take the opportunities in front of you, and think of your career as a spider web. They also talk about empty nests, reframing a midlife crisis, and the major event in Tina’s life that rerouted her toward retirement from stress.

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    9 mins
  • Bonnie Hammer on Becoming the Queen of Cable, Dreams that Keep you Stuck, and Why It’s Never a Permanent “No”
    Sep 3 2026

    Legendary media executive Bonnie Hammer sits down with host Diana Maria Riva to talk about how she went from pooper-scooping after a Hollywood stunt dog to becoming Vice Chairman of NBCUniversal and the “Queen of Cable”. As Diana dives into Bonnie's best seller 15 Lies Women Are Told at Work: And the Truths We Need to Succeed, they discuss how chasing a childhood dream can keep you stuck and why the career ladder is more of a spider web. Bonnie shares her perspective on “ageism” in the work place, how the “tougher and nastier” mindset can backfire for women, knowing your professional self worth, and has a frank discussion with Diana on not holding back with exploring greater opportunities.

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    48 mins