How Hard Can It Be? with Diana Maria Riva artwork

Self-Improvement · iHeartPodcasts

How Hard Can It Be? with Diana Maria Riva

by iHeartPodcasts

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?

Latest episodes

Showing 20 · updated from the feed

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 ch

Oct 1
50 min

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

Sep 24
44 min

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

Sep 17
36 min

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 wit

Sep 10
46 min

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 legenda

Sep 8
9 min

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

Sep 3
47 min

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

Aug 27
43 min

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

Aug 20
48 min

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 Sunn

Aug 18
10 min

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” rui

Aug 13
53 min

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 availab

Aug 6
48 min

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

Jul 30
42 min

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

Jul 23
47 min

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

Jul 21
8 min

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 sig

Jul 16
49 min

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 st

Jul 9
37 min

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 powe

Jul 2
34 min

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

Jun 30
10 min

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

Jun 25
44 min

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 a

Jun 18
33 min

Chart trend

Position in the Self-Improvement chart (US), last 90 days.

#10
all-time peak
1
day in the top 10 since May 2026

Chart positions

Where How Hard Can It Be? with Diana Maria Riva ranks today in each Apple Podcasts chart (US, Oct 3, 2026).

#147 ▲ 37 Education US
#98 ▲ 19 Self-Improvement US

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Here you find the Apple Podcasts chart positions of How Hard Can It Be? with Diana Maria Riva, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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