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.

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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 laundry.

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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.

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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.

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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 a 32-year-old suitor.

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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.

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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 BFF, setting boundaries, and why Gen X women are just getting started.
Wendy Valentine is the author of Women Waking Up: The Midlife Manifesto for Passion, Purpose, and Play and host of The Midlife Makeover Show.

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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.

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