How Hard Can It Be? with Diana Maria Riva

About 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?

Publisher

iHeartPodcasts

Category

education · health & fitness · society & culture

Language

en

Explicit

No

First episode

30 Apr 2026

Latest episode

8 Oct 2026

Latest episodes

8 of 32 episodes have a transcript.

1. 

   8 Oct 2026TRANSCRIPT

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

   Host Diana Maria Riva interviews Francia Raisa and Jessica Marie Garcia about navigating midlife realities, from perimenopause to relationships, offering insights on embracing life's next chapter.

2. 

   1 Oct 2026TRANSCRIPT

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

   Host Diana Maria Riva interviews relationship coach Sabrina Bendory about navigating toxic love, dating after 50, and redefining healthy relationships.

3. 

   24 Sept 2026TRANSCRIPT

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

   Actress Ashley Jones shares with host Diana Maria Riva insights on perimenopause, navigating divorce, and finding empowerment through day-trading.

Inside a recent episode

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

Published 8 Oct 2026 · Transcript excerpt

[…] It's right. It happened. It doesn't happen. Are we doing it? We're not doing it. What are the rules? We'll follow it. You know, whatever. And you guys learned a little bit better transition. And that's why I wonder, like, where are you with this? Well, we're such a tough generation, too. I know everyone is going to say that. But, like, we went from not having the Internet. We're the last generation to know what it's not. Like, what it's like to not have the Internet. True. And then we were kind of, like, pushed into it and had to learn more. like what what that meant and the weight of that and i feel like every generation has their own cross to bear with it like the way that you're talking about this new change i can't imagine i can't imagine because we're going through it but like you're seeing all these reels of women going through this but doing it better than you Because you're seeing this polished version of them and you're like, why can't I do that? […]

Who has been a guest on How Hard Can It Be? with Diana Maria Riva

Names identified in recent episode analyses. Showing up to five guests.

• Francia Raisa
• Jessica Marie Garcia
• Sabrina Bendory
• Ashley Jones
• Elisa Donovan

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

31 ratings

Contact How Hard Can It Be? with Diana Maria Riva

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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