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

Latest Episodes:

Ashley Jones on the AARP Ambush, Dating Profiles, and Co-Parenting After Divorce Sep 24, 2026

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 omnystudio.com/listener for privacy information.

Elisa Donovan on Grief, Saying No, and Rebuilding After Losing it All Sep 17, 2026

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 omnystudio.com/listener for privacy information.

Shaun Robinson on Aging Out Loud, the Power of Representation, and Helping the Next Generation Sep 10, 2026

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

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Happy Hour with Tina: Midlife Opportunities, Forget the Clock, and Why Won’t Our Kids Just Live With us Forever?! Sep 08, 2026

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 omnystudio.com/listener for privacy information.

Bonnie Hammer on Becoming the Queen of Cable, Dreams that Keep you Stuck, and Why It’s Never a Permanent “No” Sep 03, 2026

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 omnystudio.com/listener for privacy information.

Roselyn Sanchez on the Beauty of her 40’s and 50’s, Breaking Cycles, and Raising a Mini-me Aug 27, 2026

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 omnystudio.com/listener for privacy information.

Taylor Dayne on Why Turning 50 was Brutal, the Joys & Heartbreak of Motherhood, and Swiping Right in Midlife Aug 20, 2026

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 omnystudio.com/listener for privacy information.

Happy Hour with Tina: Some People Like Surprises, Dishwasher Loading Etiquette, and Why is Everyone Pivoting? Aug 18, 2026

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 omnystudio.com/listener for privacy information.

Sunny Hostin on her Ruined Mother’s Day, the Parenting of Adult Children, and the Lessons, Sanity, and Santeria of a 28-year Marriage Aug 13, 2026

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 omnystudio.com/listener for privacy information.

Menopause 101: Symptoms, Hormones and the Mental Toll with Dr. Suzanne Gilberg Aug 06, 2026

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 omnystudio.com/listener for privacy information.

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