On today’s Mailbag Monday, Jared covers 3 modern dating dilemmas: how to shut down a mother in law calling you “mama” without starting family drama, whether seeing bikini models on a guy’s IG Explore page plus multiple dating apps is just normal dating or a real red flag, and what it means when someone asks about your day but never follows up. Is it a lack of emotional curiosity or just bad conversational skills? Jared breaks it all down!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

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It's Pop Culture Thursday! Jared dives straight into Tom Brady and Alex Earle, breaking down their “fun fling” and the PR machine behind it. Jared also unpacks Jennifer Aniston’s low-key birthday with boyfriend Jim Curtis and what might really be behind the headlines. Then it’s Jason Bateman getting sober over “tension” with Amanda Anka, plus the latest on Brandi Glanville’s shocking health reveal. We also hit Hilaria Baldwin’s accent controversy, Shia LaBeouf’s Bourbon Street arrest, and Heidi Klum’s headline-making Grammys dress. It’s Page Six chaos, celebrity spin, and Detective JTrain connecting the dots!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

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Jared Freid welcomes comedian Shaun Murphy to Chit Chat Wednesday for a wide-ranging hang that covers stand-up life, dating, body image, nerd culture, and what happens when your comedy special includes a joke about your own skinny dick. Shaun talks about his new YouTube special Long Story Thin, growing up in Buffalo, balancing sports fandom with nerd energy, and navigating family, relationships, and confidence on stage. The two dig into watching other comedians, staying relatable when success hits, Ozempic, cookie rankings (Tate’s truthers unite), Star Wars vs Harry Potter, and why Andor might actually be the best show ever made. Plus, Jared puts Shaun through a “Nerd or Not a Nerd” game that somehow connects Zelda, Buffalo Bills trauma, and comedy authenticity.

Check out Shaun's new special today! 👉https://youtu.be/sqgJfhnpBN8?si=FJwQTzGFB9FrhHXM

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

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