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PODCAST

Double Shot of Anna: Stirring up Millennial Matters

Anna LaRocco Masi and Anna Demma

As millennials, we know that navigating the dating scene can be both exhilarating and challenging. Join us as we share humorous and heartfelt dating stories, discuss the impact of technology on modern relationships, and offer practical advice on building meaningful connections in the digital age.We"ll also dive into the unique struggles and triumphs of being a millennial. From managing student loans and saving for the future to juggling multiple passions and side hustles, we"ll explore the realities

leisure relationships

All Episodes

36:59

Birthday Blues, Princess Rules, and the Gospel of...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/07/17

Send us a text This week on Double Shot of Anna, the Annas take on the summer slump with a very special birthday countdown and a brutally honest mid-year check-in. Anna D reflects on the emotional rollercoaster of birthday season, modern dating expectations, and the art of “dilly-dallying” with a Diet Coke in hand. Meanwhile, Anna M shares updates on big creative wins, including finishing her book and launching a pet networking app. Together, they unpack the subtle difference between “princes...

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45:33

No Kings, No Sponsors, Just Two Women and a Mic

Double Shot of Anna: Stirring up Millennial Matters ·

2025/06/19

Send us a text This week on Double Shot of Anna, Anna M and Anna D dive into a raw and candid conversation about navigating life in uncertain times. From global tensions and humanitarian heartbreaks to lighthearted tales of awkward weddings, mistaken houseguests, and Olive Garden brunches, the Annas cover it all. Anna M reflects on recent travels, a surprise graduation speech, and a chaotic-yet-charming wedding in Arkansas. Anna D shares the ongoing trials of modern dating and her accidental ...

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39:27

The Meet-Cute Misfire, Thoughtful Men, and AI Wingmen

Double Shot of Anna: Stirring up Millennial Matters ·

2025/06/18

Send us a text This week’s episode is what happens when a movie moment derails into mistaken identity, mild panic, and an unexpected flirtation in the hardware aisle. The Annas kick things off with a wild “meet-cute” that’s less Notting Hill and more Oops, You're Not My Ex. From there, they dive into what makes a partner truly thoughtful—spoiler alert: it’s not flowers, it’s remembering how you organize your pantry. Then, it’s time to get real about AI in dating. Could bots be the answe...

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37:50

TSA Tantrums, Karen Read's German Shepherd, and 10...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/05/17

Send us a text Start your stopwatch, because this week's chaotic cocktail comes with travel trauma, true crime hot takes, and an unexpected PSA on emotional intelligence. The Annas kick off mid-rage with a TSA meltdown that escalates faster than a security line on a Friday night. Then it’s straight into the trial of Karen Read, where taillight conspiracy theories, sketchy Google searches, and a mysteriously missing German shepherd have us questioning everything. But it’s not all courtroom dra...

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27:56

Frontier Airlines, Bourbon Bros, and Caroline...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/04/25

Send us a text Part Two is the chaotic neutral energy we all need. Picking up mid-rant, Anna and Anna go from IRS-induced rage to AI-generated hot takes about men, and it’s honestly therapeutic. From men who ghost and then watch your Insta stories, to the universal mystery of why they all suddenly become bourbon experts, the Annas leave no stereotype un-skewered. And yes, they declare ChatGPT a better man than any living one, so do with that what you will. Then, the tables turn. It’s time for...

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25:27

Tax Day, Martial Law, Katy Perry, Trump... Is Our...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/04/18

Send us a text It may be April, but it's still cold, and the Annas have thoughts, per usual. In Part One of this spicy two-part episode, your favorite duo kicks things off with a mini weather rant and a full breakdown of Chick-fil-A’s latest nostalgia-dripping drink: the “dreamy” Dr. Pepper Spin. But the vibes quickly escalate as they spiral into a hilarious takedown of Katy Perry’s 11-minute space trip (was it empowering or just expensive cosplay?) and give unfiltered commentary on the horri...

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39:06

Ghosting, Group Chats & Festival Chaos: The Annas...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/04/03

Send us a text In Part 2, the Annas go from ghosting stats to group chat therapy. They break down how many dating profiles people swipe through in a year, the average length of a first date, and the top lies on dating apps. Height, job, and age make the list, but one of them might surprise you. They get real about the difference between ghosting and sending a breakup text, whether stalking your ex online is normal, and why unfollowing as a group is the ultimate form of solidarity. One Anna sh...

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29:42

Peeps, Bathrooms & Dental Drama: The Annas Unfiltered...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/03/28

Send us a text In Part 1 of this week’s unfiltered catch-up, Anna and Anna open with a deeply relatable story about a bad Chinese food situation and the sacredness of your own bathroom. After a chaotic detour to Five Below, they unbox Peep-themed face masks that spark an investigation into the history of Peeps, their questionable designs, and whether they’ve become the weirdest part of Easter. From there, the conversation turns to hygiene habits and public restroom etiquette. How many America...

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24:32

Ghosting, Grieving, and Good Men (Do They Exist?)

Double Shot of Anna: Stirring up Millennial Matters ·

2025/03/21

Send us a text This week on Double Shot of Anna, the Annas tackle everything from the struggles of finding a decent roommate to the unexpected emotional toll of family loss. Anna M shares a heartwarming (and slightly chaotic) story of how a friend she referred to her workplace had already been working there for weeks—without her even realizing it! Meanwhile, Anna D opens up about her grandfather’s passing, touching on the complexities of grief when family dynamics aren’t exactly smooth. The d...

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12:52

Tiny Desk Podcast like NPR but more Garage

Double Shot of Anna: Stirring up Millennial Matters ·

2025/03/13

Send us a text This week on Double Shot of Anna, Anna and Anna are coming to you live from Anna’s garage, where they’re hosting a mix of a free giveaway and a garage sale. There’s a bicycle for sale, recycling comes up, and Anna talks about Petwrk, the app she’s working on that helps pet owners set up playdates. There’s also talk about naming a coffee shop The Dark Container, which might not be the worst idea. In between all that, they talk about everything from wellness coaching and mammogra...

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26:35

Breakups, Bunkers, and the Price of Eggs: Surviving...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/03/05

Send us a text This week's episode of Double Shot of Anna is a mix of millennial musings, political reflections, and personal revelations. Anna and Anna return after a hiatus, catching up on life changes, economic struggles, and the absurdity of modern dating. They dive into personal updates, including major life transitions like divorce, new relationships, and the ever-daunting cost of living—highlighting the necessity of having multiple roommates just to survive in today’s economy. The conv...

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32:03

Web of Lies: Confronting Truths and Finding Strength...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/01/24

Send us a textIn the dramatic conclusion to this two-part series, Double Shot of Anna continues the riveting conversation with their guest as she unravels the aftermath of a deeply manipulative relationship. Picking up where the first episode left off, the Annas and their guest dive into the shocking revelations of deception, the emotional toll of uncovering the truth, and the strength it took to walk away.This episode explores the power of support systems, the importance of self-discovery, a...

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28:24

Web of Lies: A Journey Through Deception and...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/01/21

Send us a textThis week on Double Shot of Anna, the Annas sit down with a guest whose story is as complex as it is compelling. In the first part of this two-episode series, they unpack a jaw-dropping saga of unexpected connections, psychological twists, and a relationship that spiraled into a web of emotional manipulation and deception. Our guest shares her firsthand experience of navigating red flags, trauma bonding, and a tangled narrative filled with lies, control, and betrayal.From heartw...

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23:51

2025 Turning 30, Letting Go, and Embracing Change: A...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/01/14

Send us a textSUPPORT THE SHOW AT THE LINK BELOWWhat happens when two Annas come together to explore the highs, lows, and unexpected twists of life? In this captivating video, the Annas tackle everything from the societal pressures of turning 30 to the bittersweet art of saying goodbye. They dive into the balance between dreaming big and staying grounded, learning how to navigate change, and reflecting on personal growth with humor, honesty, and a shared love for life’s lessons.The Annas shar...

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24:25

From Vision Boards to Rest Days: Thriving in Chaos...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/01/11

Send us a text This week, it’s Anna and Anna taking on millennial life one meaningful conversation at a time. Together, they explore how to tackle overwhelm by focusing on small, actionable changes, the power of mastering boundaries, and how to make rest a priority in a culture of hustle.The Annas also dive into visionary thinking—how to dream big without losing sight of the present—and share tips for creating vision boards, using AI to optimize your routines, and setting realistic goals...

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37:37

One Last Laugh From Turning 30 to Mansion Dreams 2024...

Double Shot of Anna: Stirring up Millennial Matters ·

2025/01/01

Send us a text For the final episode of 2024, titled "Rediscovering Moments and Realizations", Anna reflects on the year's unexpected connections, personal milestones, and the humor in everyday revelations. This episode includes:Rediscovering Human Connection in a Digital Age: Anna shares how offline conversations at holiday parties sparked a sense of genuine connection rarely felt in today’s tech-driven world.The First to Turn 30: A funny realization about being the first in her group t...

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32:18

Anna’s Birthday Road Trip: Hikes, Hilarity, and the...

Double Shot of Anna: Stirring up Millennial Matters ·

2024/12/28

Send us a textThis week, Anna and Anna welcome back Joe Martino to relive a birthday road trip that blended spontaneity, unforgettable food, and new friendships. From the bustling streets of Memphis to the mountain views of Chattanooga, they share tales of hide-and-seek in Walmart, Southern buffet-style meals, and a hilariously disastrous Airbnb experience.Discover how their journey celebrated the spirit of connection—meeting kind strangers, navigating unexpected hurdles, and soaking up the c...

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26:27

From Tinder Swipe to "I Do" – Jane’s Love Story

Double Shot of Anna: Stirring up Millennial Matters ·

2024/12/18

Send us a textThis week, Anna and Anna welcome back Jane, who shares her incredible journey from an unexpected Tinder match to a heartfelt proposal. Jane opens up about her boyfriend Luke’s 10-day trip to the Philippines, a chaotic first meeting with her family, and a deeply personal engagement that transcended all the hiccups along the way.Discover:The surprising truth behind Luke’s Tinder profile.The challenges of long-distance love and how they made it work.A proposal story so sweet, it mi...

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33:58

Screens, Scenes, and Spotify Dreams: Modern Love and...

Double Shot of Anna: Stirring up Millennial Matters ·

2024/12/09

Send us a textThis week on Double Shot of Anna, the Annas are joined by Matthew for a lively discussion that explores everything from generational shifts in emotional experience to the intricate dance of modern dating and technology. They dive into how social media influences relationships, why dating apps might be reshaping standards, and the importance of setting boundaries in an always-online world. Plus, they reflect on the joys (and horrors) of Spotify Wrapped season and why some songs j...

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31:01

Tech Trends, Sustainability, and Family Connections:...

Double Shot of Anna: Stirring up Millennial Matters ·

2024/11/18

Send us a textThis week on Double Shot of Anna, Anna and Anna sit down with Michael LaMantia, a seasoned IT professional with over 24 years of experience, a love for golf, and a penchant for exploring new technology and renewable energy. From heartwarming family tales to forward-thinking conversations about the future, this episode offers an engaging blend of humor, insight, and inspiration.Here’s what’s brewing in this week’s double shot:Adorable Alpaca Adventures: Michael and Anna share sto...

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