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How Hard Can It Be? with Diana Maria Riva

How Hard Can It Be? with Diana Maria Riva

iHeartPodcasts 10 Episodes Jul 2, 2026

Diana Maria Riva hosts a weekly podcast for GenX women navigating midlife's challenges with humor and honesty. She invites friends from Ohio to Hollywood for unfiltered conversations about being the boss, empty nester, and caretaker while dealing with night sweats and societal expectations. The show covers topics like FUPA and hot flashes, featuring celebrity guests, experts, and allies. It's a space for unpolished, real talk about the second act of life, love, sex, and society.

Episodes

Lynn Ferguson on Radical Acceptance, Teachable Moments and 50 Words a Day Jul 2, 2026 2077 Host Diana Maria Riva sits down with Scottish actress, playwright and writer Lynn Ferguson for a conversation that swings from radical acceptance to the surprisingly powerful practice of writing just 50 words a day. See omnystudio.com/listener for privacy information.
Happy Hour with Tina: Lisa Lisa, Caring for an Ailing Parent & Folding Laundry Jun 30, 2026 624 In this Happy Hour episode of How Hard Can it Be?, host Diana Maria Riva and her bestie Tina look back at the recent conversation with music icon Lisa Lisa. They reflect on Lisa's story of caring for her mother with Alzheimer’s, drawing parallels to Tina’s own experience caring for her mom. They also discuss motherhood, redefining retirement, and the surprising self-care ritual Tina sh
Lisa Lisa on Hot Flashes, Caring for Her Mom Through Alzheimer's & Big Dreams at 60 Jun 25, 2026 2646 Host Diana Maria Riva sits down with 80’s icon Lisa Lisa for a moving conversation spanning her secret battle with breast cancer, growing up the youngest of 10 in Hell’s Kitchen, and caring for her mother through Alzheimer’s disease. Lisa openly shares with Diana her big Broadway dream, the zen art of folding clothes, and compares “mom notes’ on the challenge of detac
Kim Fields on Defying the Narrative, Purpose and Preventative Maintenance Jun 18, 2026 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
Happy Hour with Tina: Diana’s Make-Out Era, Dating App Disasters & FaceTime Bar Nights Jun 16, 2026 513 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 Bu
Constance Marie on Midlife Dating, Single Motherhood and What’s a Sesentañera? Jun 11, 2026 2710 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
A Midlife Awakening, Not a Crisis, with Wendy Valentine Jun 4, 2026 2332 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 t
Happy Hour with Tina: Love, Loss and Laughing Through Midlife Jun 2, 2026 646 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 om
Lisa Vidal on Surviving Grief, Choosing Joy and Still Being Hot at 60 May 28, 2026 2682 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 —
Gina Torres On Becoming an Empty Nester: No Carpool, No Minivan, No Identity, NO PROBLEM! May 21, 2026 1943 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/list
Happy Hour with Tina: Sleep Wars, Parenting & Not Stopping at No May 19, 2026 756 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.
Holly Robinson Peete: Never Ever Say Never... A Candid Conversation About Separate Beds, Being Critical, Autism & Midlife Joy May 14, 2026 3448 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 c

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