Dates & Mates With Damona Hoffman | Dating And Relationship Advice

This week on Dates & Mates, Damona Hoffman rewinds to her 400th episode featuring a guest who helped inspire the show from the start: the legendary Dr. Drew Pinsky. Dr. Drew has spent decades giving love, sex, and mental health advice on Loveline, Celebrity Rehab, and now on his podcast Ask Dr. Drew, which he co-hosts with his wife of over 30 years. In this vulnerable and heartfelt episode, Dr. Drew shares his personal journey through a seven-year on-and-off courtship, what finally made him ready for commitment, and how he and his wife maintain a strong marriage after decades together. Plus, he joins Damona to answer your dating questions in a special extended Dear Damona segment. What you’ll learn: Why emotional readiness matters more than "the one" How to navigate on-again/off-again dynamics with clarity When to disclose a medical condition or disability to a new partner Why gratitude and daily check-ins are key to long-term love What makes someone feel "unapproachable" in dat