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.

Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on Dates & Mates, Damona Hoffman rewinds to one of her favorite conversations with love coach and viral content creator Shaun Galanos. Shaun is the host of The Love Drive podcast and has become a rising voice in game-free, radically honest dating advice—and this episode shows you exactly why.

In this raw and radically honest episode, Shaun and Damona go head-to-head on the dating games that hold us back, how to ask for what you want in bed, and what to do when someone won’t give you a straight answer. From emotional stonewalling to the pressure of dating app perfectionism, they unpack it all.

What you’ll learn:

Why radical honesty is the only dating strategy worth mastering

How to bring up uncomfortable topics without pushing people away

What stonewalling actually says—and how to respond to it

How to explore kink, sexual compatibility, and deeper intimacy with confidence

Why optimizing for the “perfect” person might leave you lonely

How to hold your power as a strong woman without dimming your light

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

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

Listen to Sean on The Love Drive podcast and follow him @thelovedrive on Instagram and TikTok.

Learn more about your ad choices. Visit megaphone.fm/adchoices

We are back with a no-holds-barred Best of Dear Damona episode—because when it comes to texting mishaps, mixed signals, and dating curveballs, this one hits home every time.

In this candid conversation, Damona answers some of your juiciest dating dilemmas—from the accidental text that lands in the wrong inbox to what it really means when someone texts you “hey you” at 11:30 PM. She shares smart, compassionate advice on navigating confusing signals, staying grounded, and owning your truth in the dating game.

What you’ll learn:

How to respond and recover when you send the wrong text to your date

Whether it’s okay to ask for better photos—and how to do it playfully

The real timeline for exclusivity (spoiler: you don’t have to rush)

Why it’s okay to date multiple people—and how to know when to choose

How to disclose chronic conditions or disabilities with confidence

Why shared values matter more than shared hobbies

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

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

DM Damona your questions on Instagram @damonahoffman or text 424-246-6255 to be featured on a future episode.

Learn more about your ad choices. Visit megaphone.fm/adchoices

Damona breaks down the 5 core dating “loops” that keep singles stuck and the step-by-step strategies that lead to lasting love.

With over 15 years of experience coaching thousands of daters, Damona shares how clarity, mindset, and follow-through can radically shift your dating outcomes. If you’ve been swiping without success, burning out on first dates, or unsure where to even begin, this episode offers a simple and strategic path forward.

What you’ll learn:

This is a special masterclass edition of our Rewind Series, where we revisit some of the most powerful and timeless conversations from the Dates & Mates archives.

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

Want to go deeper? Learn more at DamonaHoffman.com

Join the Dating Accelerator Program

Learn more about your ad choices. Visit megaphone.fm/adchoices

Fan favorite, Dr. Orna Guralnik, renowned psychoanalyst and host of the hit Showtime series Couples Therapy, shares what decades of clinical work have taught her about love, connection, and unconscious patterns in relationships. In this conversation, Dr. Orna also opens up about the societal shifts reshaping modern intimacy, the difference between psychoanalysis and surface-level self-help, and why listening, real, curious listening, is a radical act in partnership.

What you’ll learn:

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

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

Catch Dr. Orna in Couples Therapy (streaming now on Showtime)

Follow her @ornaguralnik
NYT Essay – “I’m a Couples Therapist. Something New Is Happening in Relationships”

Learn more about your ad choices. Visit megaphone.fm/adchoices

Nick Viall, TV personality and host of the hit podcast The Viall Files, gets real about modern dating—from DM slides to ghosting games—and why the story we tell ourselves about love might be holding us back. In this candid conversation, Nick reflects on his years in the Bachelor franchise, what finally made love stick, and the overlooked ways women can help men feel safe, seen, and emotionally available. 

Plus, in a special Dear Damona & Dear Nick segment, the two team up to answer your toughest love dilemmas—from long-distance moving logistics to mixed signals that never quite become dates.

What you’ll learn:

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

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

Listen to Nick on The Viall Files podcast

Follow him on the socials @nickviall

Learn more about your ad choices. Visit megaphone.fm/adchoices

Former First Lady Michelle Obama and her brother Craig Robinson, co-hosts of the IMO Podcast, join Damona for a compelling conversation on navigating connection in the digital age. Together, they share insights into how they maintain strong family bonds across long distances and the role of technology in bridging that gap.

What You’ll Learn:

How Michelle and Craig keep connected with loved ones despite busy schedules and miles apart

The surprising benefits of texting vs. phone calls in sustaining relationships

How to bring spontaneity back to phone conversations without overwhelming your schedule

Why FaceTime and family Zoom calls became a lifeline during the pandemic—and how they continue to use them to stay close

Practical tips for setting communication boundaries that promote genuine connection

This conversation isn’t just about tech—it's about purposefully using it to deepen the relationships that matter most.

Subscribe to get every new Dates & Mates episode as soon as it drops, and don’t miss Michelle Obama and Craig Robinson on the IMO Podcast, where they explore life, love, and everything in between with candor and warmth.

Follow Michelle Obama @michelleobama

Follow Craig Robinson @craigmalrob

More about the IMO Podcast

Learn more about your ad choices. Visit megaphone.fm/adchoices

Fan favorite, Jennifer Cook, bestselling author, and autism advocate shares her experience as the on-camera expert from the hit Netflix series Love on the Spectrum. In this conversation, Jennifer also opens up about her late-in-life autism diagnosis, the challenges of dating with a neurodivergent brain, and the surprising tools that can help anyone date with more clarity and compassion.

What you’ll learn:

This is the first episode of our Rewind Series, where we revisit some of the most powerful and timeless conversations from the Dates & Mates archives. 

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

Catch Jennifer in the latest season of Love on the Spectrum (streaming now on Netflix)

Follow her @JenniferCook_Author

More at: JenniferCookAuthor.com 

Learn more about your ad choices. Visit megaphone.fm/adchoices

In this special Master Class episode, Damona explains the effect that text-based communication has had on dating today. But rather than thinking of it as us losing the art of communication, she proposes that we consider it as gaining another language and expanding our skills. Prepare to develop a communication code of conduct that will hopefully lead you to a deeper, more meaningful connection!

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

Learn more about your ad choices. Visit megaphone.fm/adchoices

Laura Day, New York Times bestselling author, shares the insights within her upcoming book, “The Prism: Seven Steps to Heal Your Past and Transform Your Future”. Her transformational tools will put you back in the driver's seat of your life and lead you to healthier relationships with others and yourself. Our Dear Damona question of the week:

• Where do you draw the line between being too picky and settling?

Pre-order your copy of Laura’s book,“The Prism: Seven Steps to Heal Your Past and Transform Your Future”, set to be released April 29th, by visiting lauraday.com/shop/

Follow Laura on Instagram @LauraDayIntuit 

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

Learn more about your ad choices. Visit megaphone.fm/adchoices