Lipstick on the Rim

Who are you when nobody needs you the same way anymore? After 25 years as a stay-at-home mom raising three kids, Helen Boulos faced the quiet house she'd dreaded for years and decided quiet wasn't her style. She taught herself Canva, launched an anonymous Instagram account under a made-up name, then dropped the alias to become the voice behind Out of Office, now one of the most candid, funny, and refreshingly unfiltered communities for women reinventing themselves in midlife.

Rather than overthinking the next chapter with notebooks, five-year plans, and a stack of self-help books, Helen makes the case for motion: start before you're ready, stay curious like a beginner, and stop second-guessing every decision. She opens up to Molly and Emese about the moment she decided to be okay, why the invisible load leaves so many moms convinced they "did nothing" for decades, and why she believes there's never been a better time to be a 50-something female entrepreneur.

Plus: what happened to her marriage once the kids left, surviving three teenagers during COVID, breaking a generational cycle through 18 years of sobriety, and why women in midlife should stop waiting for permission to do anything.

A Sony Music Entertainment production.

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Why can't we look away from complicated women who break the rules? May Cobb, the bestselling author and executive producer behind Netflix's The Hunting Wives, joins Molly and Emese to unpack our fascination with dark thrillers, complicated female characters, and the women we love to watch make terrible decisions.

Drawing on her upbringing in East Texas, May shares how Southern culture inspires her writing, why female friendships can feel more intense — and sometimes more treacherous — than romance, and why likability isn't necessarily the point.

Plus: her favorite thriller novels, why "bless your heart" might be the ultimate Southern threat, a tease of The Hunting Wives season two, and a round of thriller-writer hot takes, including who's the bigger red flag: the husband or the best friend.

A Sony Music Entertainment production.

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How does a meme account turn into Not Skinny But Not Fat? Amanda Hirsch built her platform one meme at a time back in 2016, learning early on, as she puts it, that "you can get to people just by saying something about them." A Hulu hosting gig and one surprising royal pen pal later, she's back on Lipstick on the Rim to unpack the year that pushed her out of her comfort zone and into some of the biggest rooms in pop culture.

Rather than treating her "year of yes" as permission to say yes to everything, Amanda used it to figure out exactly what's worth her time — landing on a lesson Molly sums up perfectly: the power of saying no is your biggest yes. She opens up about staying fair with her opinions on an increasingly divisive, algorithm-driven internet, and about the two interviews that left the biggest mark on her.

Plus: the story behind Amanda's one-way pen pal relationship with Meghan Markle, her take on the internet's escalating influencer-culture debates, her dream of hosting a late-night talk show, and an honest conversation about having kids in your 40s.

A Sony Music Entertainment production.

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Why is looking like yourself the hardest thing to pull off in makeup? Gucci Westman, the makeup artist behind some of the most photographed faces in Hollywood and the founder of Westman Atelier, has spent over two decades perfecting skin that looks lit from within, and this week she's teaching Molly and Emese how to achieve it.

Rather than piling on product, Gucci makes the case for a smaller, smarter "wardrobe of makeup." She explains how years of character work shaped her belief in authenticity over polish, and why the goal is never a mask. She also gets candid about scrapping an entire foundation launch to start over from scratch, and what went into the new Suprême Bio-Complex Liquid Foundation, a 30-shade formula built to keep a natural radiance all day.

Plus: her theory on choosing your foundation shade by undertone, how to bronze and warm up your skin, why every look needs a pop of color, how she contours without looking "makeup-y," and the Restraint Test: what you can skip in your routine and what you absolutely can't.

A Sony Music Entertainment production.

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Is your closet actually working for you, or are you just buying trend after trend and hoping something sticks? This season, Molly and Emese are doing fall differently — instead of chasing what's new, they're breaking down what’s actually worth buying and why the same pieces keep coming back season after season.

Rather than treating repeat styles as boring, they make the case that repetition is the smartest signal there is — if a brand keeps bringing back the same silhouette or bag year after year, it's usually because it's actually worth the investment. From cashmere knits to the perfect pair of jeans, they're walking through how to spot the pieces built to last

Plus: why lace is officially here to stay, why suede is a year-round staple, why navy is the new black, the denim styling trick that can make your look, and the jewelry rule that finishes any outfit.

Visit Macys.com for your fall fashion needs



A Sony Music Entertainment production.

Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts and follow us at @sonypodcasts

To bring your brand to life in this podcast, email podcastadsales@sonymusic.com

Mentioned in the Episode: https://shopmy.us/shop/collections/7661762

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