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

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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”

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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

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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

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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 

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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

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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

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Damona shares a rare peek behind the curtain of one of her private coaching sessions, with the client’s permission of course! Hear firsthand how she teaches her clients to use their own intuition in dating and beyond. Plus you’ll get to see exactly how Damona uses her own intuition while coaching singles in love from how to tune in, what to look and listen for, and exercises to get started yourself. Whether you’ve been ignoring your gut or just want to sharpen your instincts, this episode is going to help you reconnect with one of your most powerful dating tools—you.

Interested in booking your own solo coaching session? Email [email protected] or DM @damonahoffman on Instagram or Facebook!

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Francesca Hogi, TED speaker and host of the Dear Franny podcast, introduces her new book, “How To Find True Love: Unlock Your Romantic Flow and Create Lasting Relationships.” Plus, she will break down her new definition of true love, dive deeper into the Fairy Tale Industrial Complex, explore her meet-cute mindset and so much more! Our Dear Damona question of the week:

• Dating apps keep feeding me the same old matches, so how do I meet someone IRL?

Grab your copy of Francesca’s book, “How to Find True Love: Unlock Romantic Flow and Create Lasting Relationships”, by visiting FrancescaHogi.com/Book

Follow Francesca on Instagram @DearFranny 

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

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Sharing a new show from our friends at Higher Ground, hosted by Michelle Obama, called IMO. On IMO, Michelle and her big brother Craig Robinson bring candid perspectives to the everyday questions shaping our lives, relationships and the world around us. Each week, they’re joined by a guest to tackle real questions from real folks just like you offering practical advice, personal storytelling, and plenty of laughs. And a lot of their questions are about dating and relationships. Michelle and Craig share stories about being there for each other throughout their lives, from first crushes and fraught college years, to landing at the White House, to losing their mom. For six decades they’ve been each others’ most trusted counsel—and now, they want to be that counsel for you. In this episode, renowned life coach and podcaster Jay Shetty joins Michelle and Craig to puzzle through a listener's question about professional ambition and dating. The trio discuss money in relationships, finding balance between work and romance, and Michelle shares her advice for choosing a life partner. They ask: Is the pursuit of perfection—in work or dating—worth it? You can hear more episodes of IMO at https://lnk.to/imomichellecraigDM

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