How Hard Can It Be? with Diana Maria Riva

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

Episodes

August 6, 2026 48 mins

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 Alzhei...

Listen
Watch
Mark as Played

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 privacy information.

Listen
Watch
Mark as Played

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/listener for privacy information.

Listen
Watch
Mark as Played

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.

Listen
Watch
Mark as Played

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/listener for privacy information.

Listen
Watch
Mark as Played

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 privacy information.

Listen
Watch
Mark as Played

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.

Listen
Watch
Mark as Played

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 shares with Lisa Lisa: folding laundr...

Listen
Watch
Mark as Played

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 detaching from their children.

See omnyst...

Listen
Watch
Mark as Played

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 never tired of the work.

See omnyst...

Listen
Watch
Mark as Played

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 Builder" lookalikes and turning down ...

Listen
Watch
Mark as Played

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 Constance compare notes and dive in deep.

...

Listen
Watch
Mark as Played

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 the importance of becoming your own ...

Listen
Watch
Mark as Played

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 omnystudio.com/listener for privacy i...

Listen
Watch
Mark as Played

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 — bingo wings, chin hairs, disappeari...

Listen
Watch
Mark as Played

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/listener for privacy information.

Listen
Watch
Mark as Played

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.

Listen
Watch
Mark as Played

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 conversation full of laughs and movi...

Listen
Watch
Mark as Played

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 celebrate the power of asking "why not...

Listen
Watch
Mark as Played

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 it all: the company you keep, the ...

Listen
Watch
Mark as Played

Popular Podcasts

    Betrayal Weekly is back for a new season. Every Thursday, Betrayal Weekly shares first-hand accounts of broken trust, shocking deceptions, and the trail of destruction they leave behind. Hosted by Andrea Gunning, this weekly ongoing series digs into real-life stories of betrayal and the aftermath. From stories of double lives to dark discoveries, these are cautionary tales and accounts of resilience against all odds. From the producers of the critically acclaimed Betrayal series, Betrayal Weekly drops new episodes every Thursday. If you would like to share your story, you can reach out to the Betrayal Team by emailing them at betrayalpod@gmail.com and follow us on Instagram at @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

    Crime Junkie

    Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    The Bobby Bones Show

    Listen to 'The Bobby Bones Show' by downloading the daily full replay.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices