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 dating and how to shift it

How to know when you're ready to date after trauma or burnout

This episode is part of our Rewind Series, where we revisit some of the most timeless and transformative conversations from the Dates & Mates archive.

Subscribe now to catch every Rewind drop and our Spring bonus episodes the moment they go live.

Listen to more of Dr. Drew on the Ask Dr. Drew podcast and follow him @drdrewpinsky.

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