How Hard Can It Be? with Diana Maria Riva

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Ranking history

About the show

Latest episodes

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

  October 1, 2026 · 50 min

  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…

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

  September 24, 2026 · 44 min

  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…

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

  September 17, 2026 · 37 min

  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…

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

  September 10, 2026 · 46 min

  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…

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

  September 8, 2026 · 9 min

  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…

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

  September 3, 2026 · 48 min

  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…

• Roselyn Sanchez on the Beauty of her 40’s and 50’s, Breaking Cycles, and Raising a Mini-me

  August 27, 2026 · 44 min

  Actor/Director Roselyn Sanchez (Without a Trace, Rush Hour 2, Devious Maids) joins the show to talk about what midlife can look like when you refuse to slow down and why she considers her 40’s & 50’s her greatest hits. Becoming a mom later…

• Taylor Dayne on Why Turning 50 was Brutal, the Joys & Heartbreak of Motherhood, and Swiping Right in Midlife

  August 20, 2026 · 49 min

  Pop and R&B icon Taylor Dayne joins the show and opens up about why turning 50 was the most brutal birthday of her life, her colon cancer diagnosis, and losing “the love of her life”. Taylor also shares her experience of becoming a single…