104| WHO'S YOUR ZADDY? 1 GAY + 1 STRAIGHT = DATING CHAOS! 🌈🚩🫖 | GUEST: CHRISTOPHER WINTER

107 | STILL GAME | DATING, SEX & SWIPING AFTER 60! GUESTS: TRIXIE & JOE

Send us Fan Mail [https://www.buzzsprout.com/2469840/fan_mail/new] Description: In the Season 1 finale of Hey Girl, U Up?, Anna sits down with two unforgettable singles proving that dating, sex, flirting, ghosting, tequila, games, and bad decisions absolutely do NOT expire after 60. Meet Trixie — 83 years old, dating younger men, driving muscle cars, collecting unsolicited dick pics, and still closing bars at 2AM. Alongside Joe from Jersey, a lifelong bachelor who treats dating like a competitive sport, this episode dives into modern dating, loneliness, hookups, dating apps, red flags, aging, romance scams, and why “the game” never really ends. It’s STILL GAME — a hilarious, chaotic, surprisingly heartfelt conversation about staying curious, staying single, and staying alive. Topics this episode include: * Dating, sex, and swiping after 60, 70, and 80 * DateACougar and dating younger men * One-night stand rules and why nobody wants sleepovers anymore * Tequila nights, bars, flirting, and Casa Vega happy hours * Ghosting, lying about age, and fake dating profiles * Tinder “Free Tonight,” nanoships, and textationships * Romance scammers and people asking for money online * Red flags, toxic traits, and “the game” * Why some people stay single by choice * The most romantic gestures they’ve ever experienced * Dating advice from two people who have truly seen it all From muscle cars and margaritas to dick pics and emotional games, this episode explores what happens when people keep searching for connection long after society expects them to stop. And maybe the biggest takeaway of all: dating never really ends. Follow Hey Girl, U Up?: 🔗 Follow the Madness: 📺 Youtube Video Podcast: https://www.youtube.com/@HeyGirlUup 📱 TikTok: https://www.tiktok.com/@heygirluup 📸 Instagram: https://www.instagram.com/heygirluup [https://www.instagram.com/heygirluup] 🌐 Website: https://www.heygirluup.com/ [https://www.heygirluup.com/] 📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502 [https://www.facebook.com/heygirluup]

106 | I WON'T SETTLE! - PICKY, PERFECT OR PEACE? | GUEST: GRACE LEWIS

Send us Fan Mail [https://www.buzzsprout.com/2469840/fan_mail/new] What’s the difference between being picky, having standards, and finally protecting your peace? In this week’s episode, Anna sits down with powerhouse guest Grace Lewis—author, reality dating alum, life coach and unapologetic boss—to talk about the real cost of dating down, how childhood shapes our romantic choices, and why neither of them is willing to settle (ever again). This is a no-filter conversation between two smart, successful women who’ve tried it all—from dating apps and matchmakers to love stories that felt right until they very much weren’t. They unpack red flags, ghosting, and the emotional acrobatics women perform when we fall for potential instead of reality. From LA’s fake job titles to New York’s direct charm, from air mattresses to FaceTime background sleuthing—this episode is part hilarious, part heartfelt, and totally relatable. Whether you’ve ever paid the emotional (or literal) bill for someone else’s lack of ambition—or just needed a reminder that not settling is a power move—this one’s for you. 🔗 Follow the Madness: 📺 Youtube Video Podcast: https://www.youtube.com/@HeyGirlUup 📱 TikTok: https://www.tiktok.com/@heygirluup 📸 Instagram: https://www.instagram.com/heygirluup [https://www.instagram.com/heygirluup] 🌐 Website: https://www.heygirluup.com/ [https://www.heygirluup.com/] 📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502 [https://www.facebook.com/heygirluup]

105| PETER PAN - THE LOST (SINGLE) BOYS!| GUESTS: NEIL BENTLEY FIERRO & DREW LEWANDOWSKI

Send us Fan Mail [https://www.buzzsprout.com/2469840/fan_mail/new] Why are so many men over 40 still single, never married, and child-free? Are they emotionally unavailable? Lovable lone wolves? Or just playing the long game? In this episode of Hey Girl, U Up?, Anna sits down with two real-life “Lost Boys” — Neil Bentley Fierro and Drew Lewandowski — for a wide-ranging, hilarious, and at times brutally honest conversation about modern dating, commitment fears, and what it means to grow up (or not) in the era of endless swiping. Drew is a self-proclaimed hopeless romantic with a long trail of almosts, while Neil prefers meeting women “in the wild” and dreams of a traditional cheerleader-style partner — minus the emotional labor. Together, they dive into what men really want, what turns them off, and why dating after 40 is such a minefield for both sides. From explosive first-date disasters and ghosting regrets to the pros and cons of single moms, religious dealbreakers, and sex on the first night, this episode is packed with sharp takes, big laughs, and surprising vulnerability. We also play "Regret Roulette," roast the wildest dating bios in our weekly "Biohazard" segment, and rank red flags with “Flagged or Bagged.” If you've ever wondered why some men never seem to settle down — or if you're dating one right now — this is the episode that pulls back the curtain. No shame, no sugarcoating. Featuring confessions, contradictions, and just enough espresso martinis to keep it spicy, Peter Pan – The Lost (Single) Boys is a must-listen for anyone navigating the strange, funny, and often frustrating world of dating over 40. Follow the show at heygirluup.com or on Instagram and TikTok @heygirluup. New episodes every week. 🔗 Follow the Madness: 📺 Youtube Video Podcast: https://www.youtube.com/@HeyGirlUup 📱 TikTok: https://www.tiktok.com/@heygirluup 📸 Instagram: https://www.instagram.com/heygirluup [https://www.instagram.com/heygirluup] 🌐 Website: https://www.heygirluup.com/ [https://www.heygirluup.com/] 📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502 [https://www.facebook.com/heygirluup]

104| WHO'S YOUR ZADDY? 1 GAY + 1 STRAIGHT = DATING CHAOS! 🌈🚩🫖 | GUEST: CHRISTOPHER WINTER

Send us Fan Mail [https://www.buzzsprout.com/2469840/fan_mail/new] It’s Pride Month, and we’re serving rainbows, red flags, and dating chaos. In this episode, host Anna sits down with Christopher — a sharp-witted dater navigating dating after 40 — to compare battle scars, best dates, and bizarre bios across gay and straight dating! From Grindr to ghosting, ENM to energy vampires, it’s one hilarious, unfiltered conversation about what it’s really like to swipe, sext, and survive in today’s dating jungle. Segments include: * Regret Roulette: Grocery store stalkers and high-risk sexting * Flagged or Bagged: Age fibbers, nuders, and no-douchers * Biohazard: Van life, Anne Hathaway, and dating tape bios * Terms of Endearment: Cloaking, mosting, tin-stagramming Whether you’re into tops, texts, or 2 a.m. voice notes, this one’s for anyone who’s ever been single, confused, and dangerously hopeful!! New episodes drop weekly. Visit heygirluup.com [https://www.heygirluup.com] for more. 🔗 Follow the Madness: 📺 Youtube Video Podcast: https://www.youtube.com/@HeyGirlUup 📱 TikTok: https://www.tiktok.com/@heygirluup 📸 Instagram: https://www.instagram.com/heygirluup [https://www.instagram.com/heygirluup] 🌐 Website: https://www.heygirluup.com/ [https://www.heygirluup.com/] 📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502 [https://www.facebook.com/heygirluup]

103 | SHIPWRECKED - LOST AT SEA IN THE DATING WORLD!| GUEST: TANNA FREDERICK

Send us Fan Mail [https://www.buzzsprout.com/2469840/fan_mail/new] 🎧 This week on Hey Girl, U Up?, we’re officially lost at sea in the dating world. We're not dating but we are definitely not not dating???From relationships to situationships, textationships to nanoships — we're talking about all the ships that don’t float. Why do we stay stuck? Why can’t we define things? And how the hell do you know when you’re in a situationship... or just emotionally stranded?  Our guest this week is the brilliant and hilarious Tanna — writer, director, actress, and fellow single woman — who joins Anna to unpack the emotional whiplash of modern dating. Together they swap wild stories, real regrets, and laugh their way through the wreckage. Topics include:  – What even is a situationship? – House dates: sexy or serial killer starter pack? – A Fiat Panda. A one-night stand. You do the math. – The butt pic template — yes, women have them too – Uncle Yoda’s missing 4th step in the formula for love – “We sleep together and talk every day, but we’re not dating…” – Comedians, cat dads, men without cars, and red flag roulette – When you’ve done his laundry but still don’t have a label Set in Los Angeles, where dating traffic is somehow worse than the 405. Whether you're deep in the dating pool or treading emotional water, this episode is for anyone who’s ever been stuck on a ship with no sail and no Wi-Fi. Hey Girl, U Up? is your brutally honest, hilarious, and unfiltered guide to dating, love, sex, and surviving the chaos — one cringe story at a time. #DatingPodcast #Situationships #Shipwrecked #DatingFails #HeyGirlUUp #RedFlags #Textationships #SingleLife #ModernDating #Ghosting #DatingHumor 🔗 Follow the Madness: 📺 Youtube Video Podcast: https://www.youtube.com/@HeyGirlUup 📱 TikTok: https://www.tiktok.com/@heygirluup 📸 Instagram: https://www.instagram.com/heygirluup [https://www.instagram.com/heygirluup] 🌐 Website: https://www.heygirluup.com/ [https://www.heygirluup.com/] 📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502 [https://www.facebook.com/heygirluup]