Jared Freid | How a Walking Red Flag Became Boyfriend Material!

#958. Somehow the guy who built a career talking about being single... has a girlfriend.

Jared Freid joins Kaitlyn to share how he ended up getting back together with the woman he once broke up with, why writing his new book Walking Red Flag forced him to relive every dating mistake he's ever made, and what finally changed for him when it came to commitment.

From dating apps and first-date hot takes to the "icks" that are actually valid, Jared shares the dating advice women actually want to hear. He also opens up about taking a year off alcohol, why it unexpectedly changed his life, the surprising reason he decided to try Ozempic, and how he's navigating a healthy relationship after years of talking about dating for a living.

If you've ever overanalyzed a text, questioned someone's mixed signals, or wondered if modern dating is just... broken, this episode is for you.

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