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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.

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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 for more.

🔗 Follow the Madness:

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📱 TikTok: https://www.tiktok.com/@heygirluup
📸 Instagram: https://www.instagram.com/heygirluup
🌐 Website: https://www.heygirluup.com/
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🎧 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
🌐 Website: https://www.heygirluup.com/
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