From Threesomes to Non-Monogamy: One Man's Journey Beyond Jealousy and Shame episode artwork

EPISODE · Nov 28, 2025 · 1H 19M

From Threesomes to Non-Monogamy: One Man's Journey Beyond Jealousy and Shame

from Oh F*ck Yeah with Ruan Willow · host Ruan Willow

Episode 695: From Threesomes to Non-Monogamy: One Man's Journey Beyond Jealousy and Shame with author Adam Darrow about his edgy, honest, and raw memoir "Seek the Risk" (affiliate link) https://amzn.to/3KrboVR When Adam Darrow met Jane at forty, he thought he was the adventurous one. After all, he'd spent his twenties competing in extreme sports and had explored threesomes—that made him pretty edgy, right? Then Jane, a PhD psychologist who spoke five languages, told him she didn't do boyfriends (and she meant it). Drawing from his background in extreme sports, Darrow spent two and a half years transitioning into non-monogamy, followed by three challenging years of emotional work before finding equilibrium. The journey wasn't easy. When Jane publicly announced their arrangement on Facebook in 2009, Darrow watched his life wildly transform. His best friend called him derogatory names. But over time, he discovered something unexpected: jealousy could be channeled into motivation to become a better partner. What initially felt emasculating became an opportunity to overcome deep-seated insecurities like imposter syndrome and validation-seeking. His memoir chronicles this transformative experience through vulnerable storytelling that includes explicit extreme sexual details and uncomfortable emotional truths, as well as healing and growth. How did keeping emotions bottled up nearly break him? The book explores that question while advocating for moving beyond societal shame around sexuality, relationship conformity, and focusing on personal authenticity rather than rigid beliefs about relationships. Estimated Timeline:  Adam Darrow's Journey Into Non-Monogamy 00:03:40 - PhD Psychologist with Unconventional Past 00:06:43 - Extreme Sports Skills Applied to Non-Monogamy 00:09:13 - Separating Sex from Emotion in Relationships 00:19:57 - Managing Jealousy Through Don't Ask, Don't Tell 00:22:26 - From Jealousy to Compersion in Open Relationships 00:25:11 - Breaking Through Shame and Choosing Each Other 00:28:42 - Walking the Beach: Questioning My Limits, book excerpt 00:33:17 - Understanding Nesting Couples and Non-Monogamy 00:39:43 - Letting Go of Control in Relationships 00:46:22 - Vulnerability and Authenticity in Memoir Writing 00:51:51 - Writing the Book and Her Reaction 00:58:17 - Identity Beyond Sexual Acts, sexuality 01:06:44 - Overcoming Jealousy Through Personal Growth 01:11:27 - Healthy vs Unhealthy Jealousy in Relationships Connect with Adam Darrow:  Link to the books website  www.seektherisk.net Substack seektherisk.substack.com Email for folks to contact Adam at [email protected] insta:   @seektherisk Support the show Newsletters https://subscribepage.io/ruanwillow https://linktr.ee/RuanWillow Affiliate Firm Tech 15% OFF with code ruan15 https://myfirmtech.com/ruanwillow

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From Threesomes to Non-Monogamy: One Man's Journey Beyond Jealousy and Shame

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This episode is 1 hour and 19 minutes long.

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This episode was published on November 28, 2025.

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Episode 695: From Threesomes to Non-Monogamy: One Man's Journey Beyond Jealousy and Shame with author Adam Darrow about his edgy, honest, and raw memoir "Seek the Risk" (affiliate link) https://amzn.to/3KrboVR When Adam Darrow met Jane at forty, he...

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