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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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