Podcast

How Hard Can It Be? with Diana Maria Riva

Education, Relationships, Self-Improvement, Society & Culture

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 second act of life, love, sex and society, as we ask… How hard can it be?

Episodes
35
Releases
Weekly
Typical length
45 min
On air since
2026
Latest episode
5 days ago

Episodes

35 episodes, newest first

  1. Anjali Bhimani on Going After Your Dreams, Dealing with Grief, and Why Midlife isn’t All Downhill

    Season 1, Episode 26

    Show notes

    Actress Anjali Bhimani (Ms. Marvel, Overwatch, Apex Legends) stops by the show to talk about the challenges of choosing a career in TV/film in an Indian household, how she learned she doesn’t have to go through life with her fists up, and the loss that taught her how to move through grief and how to recognize her emotional triggers. Anjali also discusses the beauty of exploring new pursuits in life, and how her typical dislike of self-help books prompted her to write one of her own, “I Am Fun Size, And So Are You."

    You can find Anjali's book here.

    See https://omnystudio.com/listener for privacy information.

    44 min
  2. Domestic Violence Awareness Month: A Survivor’s Story and Where to Find Help

    Season 1, Episode 25

    Show notes

    Content warning: This episode talks about domestic violence, relationship abuse, emotional control and coercive control. Please listen with care. You can reach the National Domestic Violence Hotline 24/7, in English and Spanish, at 1-800-799-7233 or by texting START to 88788.

    October is Domestic Violence Awareness Month. Today, host Diana Maria Riva talks with actress and producer Sara Portillo who shares her story of surviving an abusive relationship that started when she was a teenager and lasted nearly 30 years. She talks about the trauma bond, the isolation and the cycle of abuse, and about how she rebuilt her life and learned to love herself again.

    Diana is also joined by attorney Carmen McDonald and licensed clinical social worker Sylvia Gribble from the Survivor Justice Center, to discuss ways to help survivors, the legal options and resources available to them, and how to support and help a loved one you suspect is experiencing domestic violence.

    Look for the QR code in this episode for resources or click here.

    See https://omnystudio.com/listener for privacy information.

    51 min
  3. Maria Hinojosa on the Importance of Independence in a Marriage, Asking Your Kids for Forgiveness, and Being a ‘Wisdom Elder'

    Season 1, Episode 24

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

    46 min
  4. Millennials vs. Gen X: Comparing Notes on Midlife with Francia Raisa & Jessica Marie Garcia

    Season 1, Episode 23

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

    51 min
  5. Toxic Love, the Sex and the City Paradox, and Dating Right after 50 with Sabrina Bendory

    Season 1, Episode 22

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

    50 min
  6. Ashley Jones on the AARP Ambush, Dating Profiles, and Co-Parenting After Divorce

    Season 1, Episode 21

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

    44 min
  7. Elisa Donovan on Grief, Saying No, and Rebuilding After Losing it All

    Season 1, Episode 20

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

    37 min
  8. Shaun Robinson on Aging Out Loud, the Power of Representation, and Helping the Next Generation

    Season 1, Episode 19

    Show notes

    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

    See https://omnystudio.com/listener for privacy information.

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

    Season 1

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

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

    Season 1, Episode 18

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

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

    Season 1, Episode 17

    Show notes

    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 what longevity truly means. All this and the secrets of her long marriage with actor Eric Winter.

    See https://omnystudio.com/listener for privacy information.

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

    Season 1, Episode 16

    Show notes

    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 using her own song titles.

    See https://omnystudio.com/listener for privacy information.

    49 min
  13. Happy Hour with Tina: Some People Like Surprises, Dishwasher Loading Etiquette, and Why is Everyone Pivoting? Bonus

    Season 1

    Show notes

    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.

    See https://omnystudio.com/listener for privacy information.

    10 min
  14. Sunny Hostin on her Ruined Mother’s Day, the Parenting of Adult Children, and the Lessons, Sanity, and Santeria of a 28-year Marriage

    Season 1, Episode 15

    Show notes

    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 choosing instead of being chosen. All followed by actor Gina Torres surprise crashing the studio and joins the conversation to discuss the benefits of “Panda Time” and the art of breaking your own shit when making a point.

    See https://omnystudio.com/listener for privacy information.

    53 min
  15. Menopause 101: Symptoms, Hormones and the Mental Toll with Dr. Suzanne Gilberg

    Season 1, Episode 14

    Show notes

    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 shocking statistics of dementia and Alzheimer’s diagnosis in women, Diana and Dr. Gilberg discuss what perimenopause and menopause can actually look like, as well as the healthy and proactive ways to stay informed and empowered in self advocacy. Their in-depth dialogue also taps into the mental health component, and those “I need a RX for my UTI..” phone calls to your doctor at 5:01pm on a Friday.

    Find The Menopause Bootcamp here.

    Find Dr. Gilberg's resource sheet here.

    See https://omnystudio.com/listener for privacy information.

    49 min
  16. Family Lies: The Secrets, Surprises, and Survival of it all, with Carmen Rita Wong

    Season 1, Episode 13

    Show notes

    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 https://omnystudio.com/listener for privacy information.

    43 min
  17. Justina Machado: Finding Joy, Dating Apps After 50, and Giving Less F**ks

    Season 1, Episode 12

    Show notes

    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 https://omnystudio.com/listener for privacy information.

    48 min
  18. Happy Hour with Tina: Surrendering Control, Solitude, and Why Don’t we Dance More? Bonus

    Season 1

    Show notes

    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 https://omnystudio.com/listener for privacy information.

    9 min
  19. Toxic Productivity, the Perfectionism Trap and the Power of Rest with Israa Nasir

    Season 1, Episode 11

    Show notes

    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 https://omnystudio.com/listener for privacy information.

    49 min
  20. Judy Reyes on Finding Your Voice, Sitting in Your Power and Ignoring the Clock

    Season 1, Episode 10

    Show notes

    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 https://omnystudio.com/listener for privacy information.

    37 min

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