How Hard Can It Be? with Diana Maria Riva
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
Millennials vs. Gen X: Comparing Notes on Midlife with Francia Raisa & Jessica Marie Garcia
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 cha
Toxic Love, the Sex and the City Paradox, and Dating Right after 50 with Sabrina Bendory
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 vie
Ashley Jones on the AARP Ambush, Dating Profiles, and Co-Parenting After Divorce
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, age
Elisa Donovan on Grief, Saying No, and Rebuilding After Losing it All
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
Shaun Robinson on Aging Out Loud, the Power of Representation, and Helping the Next Generation
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 w
Happy Hour with Tina: Midlife Opportunities, Forget the Clock, and Why Won’t Our Kids Just Live With us Forever?!
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 m
Bonnie Hammer on Becoming the Queen of Cable, Dreams that Keep you Stuck, and Why It’s Never a Permanent “No”
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 stu
Roselyn Sanchez on the Beauty of her 40’s and 50’s, Breaking Cycles, and Raising a Mini-me
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 in life, Roselyn shares how parenthood forced her to finally confront past family trauma. the beauty and challenges of raising a mini-me, and wh
Taylor Dayne on Why Turning 50 was Brutal, the Joys & Heartbreak of Motherhood, and Swiping Right in Midlife
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 mom of twins via surrogacy and the reality of dating apps. And stay for a rapid-fie round where Taylor answers midlife’s hardest questions
Happy Hour with Tina: Some People Like Surprises, Dishwasher Loading Etiquette, and Why is Everyone Pivoting?
It’s time for a new Happy Hour episode of How Hard Can it Be? and this week, Diana and her bestie Tina recap the recent conversation with Sunny Hostin. They get into Sunny’s ruined Mother’s Day trip to Mexico, whether they’re an architect or a raccoon on crack when it comes to loading the dishwasher and why “pivoting” has become the word of this season of life.
Sunny Hostin on her Ruined Mother’s Day, the Parenting of Adult Children, and the Lessons, Sanity, and Santeria of a 28-year Marriage
The View’s Sunny Hostin joins host Diana Maria Riva to discuss how she’s been dealing with midlife’s most fantastic BS. Sunny talks about how her husband’s “surprise” ruined her Mother’s Day celebration and how it’s all part of the secret to a long-lasting marriage, a parent’s involvement in their kids’ romantic lives, and the power of ch
Menopause 101: Symptoms, Hormones and the Mental Toll with Dr. Suzanne Gilberg
Host Diana Maria Riva is joined by OB/GYN Dr. Suzanne Gilberg as they dive head first into a deep discussion on menopause and the vast information and science now available to women. From the more obvious symptoms such as brain fog, mood swings, and low sex drive, to the less obvious like heart disease, type 2 diabetes , and other silent effects of inflammation. Covering topics such as the shockin
Family Lies: The Secrets, Surprises, and Survival of it all, with Carmen Rita Wong
Author Carmen Rita Wong joins the show to unpack the family secret that rewrote her identity at 30. Carmen shares the wild story that led to her book “Why Didn’t You Tell Me” (including a Star Wars-style confession), what she thinks about forgiveness vs. understanding, and gives us a masterclass in refusing to carry someone else’s baggage.See omnystudio.com/listener for pri
Justina Machado: Finding Joy, Dating Apps After 50, and Giving Less F**ks
Actress Justina Machado joins host Diana Maria Riva to talk about their hilarious case of mistaken identity, the harsh reality of dating apps, the FUPA revelation and why society’s expiration date on women is total BS. Justina also shares why turning 50 hit hard and yet achieved one of her biggest dreams after the fact, all while mastering the art of giving less f**ks.See omnystudio.com/list
Happy Hour with Tina: Surrendering Control, Solitude, and Why Don’t we Dance More?
Diana and Tina recap the recent episode with Judy Reyes. They dig into the themes that resonated with them, including learning to be alone, the struggle to just be still and the lost art of dancing.See omnystudio.com/listener for privacy information.
Toxic Productivity, the Perfectionism Trap and the Power of Rest with Israa Nasir
Host Diana Maria Riva is joined by therapist and author Israa Nasir to talk about toxic productivity, the dangers that come with it and how to recognize those warning signs. They will dive deep into exploring why being “busy” can mask itself as self-care and perfectionism, and how our self-worth can get tangled up in our desired achievements. Get Israa's book here.See omnystudio.com/li
Judy Reyes on Finding Your Voice, Sitting in Your Power and Ignoring the Clock
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 pri
Lynn Ferguson on Radical Acceptance, Teachable Moments and 50 Words a Day
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
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
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
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
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?
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
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
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
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!
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
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
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?"
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"
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
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