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:
How to slide into DMs without overthinking it
Why the “how we met” story isn’t as important as we think
What men wish women knew about emotional safety
How to handle a situationship that keeps circling back
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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31:03
Michelle Obama & Craig Robinson Communication Q&A Minisode
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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7:24
Love on the Spectrum & Sensory Overload: REWIND
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:
How neurodiverse and neurotypical daters alike can build intentional communication
Practical tools for managing sensory overwhelm on a date
The subtle power of “tell me more”
Why preparation and presence are the keys to connection
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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35:52
Master Class: The Texting Trap
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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57:42
The Prism & Too Picky
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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From navigating dating apps to overcoming the friendzone to seeking a soulmate, this ain’t your momma’s love advice! Hosted by the Official Love Expert of The Drew Barrymore Show and LA Times advice columnist, Damona Hoffman, Dates & Mates is jam-packed with interviews from your favorites celebs, authors, and experts.
Dates & Mates is the 2022 Winner of The Best Podcast of the Year at The Black Podcasting Awards, #1 ranked love and relationship podcast by Cosmopolitan Magazine and a Top 10 Pick by HuffPost in the love category.