Jared is joined by Dr. Naomi Bernstein of the Oversharing podcast to unpack dating after divorce, performance anxiety, and whether taking intimacy slow signals emotional baggage. They break down an email from a 34-year-old woman dating a gentle, recently divorced man who says something “deeper than biology” is blocking intimacy. Then they debate if a flight attendant was right to tell a 30-year-old guy he’s “too nice for casual dating.” Plus: performance anxiety, people pleasers, alpha vs beta energy, and why sexual chemistry doesn’t always match long-term potential. Jared and Dr. Naomi get deep and at one point, when Jared asks Dr. Naomi to give him real advice about his own dating life!

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