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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:

Midlife Makeup Secrets, Must-Haves, and AbraCADAVER No More with Makeup Guru Erica Taylor Nov 05, 2026

Show notes

The midlife makeup guru herself, Erica Taylor, joins the show this week to re-route your routine! She discusses the importance of skin prepping, how exfoliating is often the un-sexy answer to great makeup, and puffy versus sunken eyes remedies. Diana also dives into makeup myths or magic, Erica's favorite drugstore buys, and the one product she wouldn’t dare be buried without.

You can find Erica’s book “The Magic of Makeup: Your Handbook for a Youthful, Radiant Look” here.

See omnystudio.com/listener for privacy information.

Anjali Bhimani on Going After Your Dreams, Dealing with Grief, and Why Midlife isn’t All Downhill Oct 29, 2026

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 omnystudio.com/listener for privacy information.

Domestic Violence Awareness Month: A Survivor’s Story and Where to Find Help Oct 22, 2026

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 omnystudio.com/listener for privacy information.

Maria Hinojosa on the Importance of Independence in a Marriage, Asking Your Kids for Forgiveness, and Being a ‘Wisdom Elder' Oct 15, 2026

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 omnystudio.com/listener for privacy information.

Millennials vs. Gen X: Comparing Notes on Midlife with Francia Raisa & Jessica Marie Garcia Oct 08, 2026

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.

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Toxic Love, the Sex and the City Paradox, and Dating Right after 50 with Sabrina Bendory Oct 01, 2026

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 omnystudio.com/listener for privacy information.

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.

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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.

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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.

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