Send us a text

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
🌐 Website: https://www.heygirluup.com/
📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502

Send us a text

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
🌐 Website: https://www.heygirluup.com/
📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502

Send us a text

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:

📺 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/
📘 Facebook: https://www.facebook.com/profile.php?id=61573461766502