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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 se...
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Episodes
Judy Reyes on Finding Your Voice, Sitting in Your Power and Ignoring the Clock 09.07.2026 37:08
Actress Judy Reyes (Scrubs, High Potential, Claws) joins the show to talk about her midlife moment of choosing motherhood in her 40’s, bringing Nurse Carla's menopause storyline to the Scrubs revival and the power of finally trusting your own voice. Judy also opens up about forgiveness, facing the intimidation of big dreams, and ultimately, fulfilling them. See omnystudio.com/listener for pr...
Lynn Ferguson on Radical Acceptance, Teachable Moments and 50 Words a Day 02.07.2026 34:37
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 30.06.2026 10:24
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 25.06.2026 44:06
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 18.06.2026 33:46
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 16.06.2026 8:33
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? 11.06.2026 45:10
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 04.06.2026 38:52
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 02.06.2026 10:46
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 o...
Lisa Vidal on Surviving Grief, Choosing Joy and Still Being Hot at 60 28.05.2026 44:42
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! 21.05.2026 32:23
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/lis...
Happy Hour with Tina: Sleep Wars, Parenting & Not Stopping at No 19.05.2026 12:36
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 14.05.2026 57:28
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...
Happy Hour with Tina: Pivoting, Saying No and Asking “Why Not?" 12.05.2026 9:58
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 cel...
Eva Longoria on Midlife: GirlSquads, Sleep Secrets, and Saying "No" 07.05.2026 1:00:26
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...
Introducing: How Hard Can It Be? with Diana Maria Riva 30.04.2026 1:28
See omnystudio.com/listener for privacy information.
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