Episode 2477: How Daniel Oppenheimer Learned That the Problem in his Marriage Was Himself episode artwork

EPISODE · Mar 25, 2025 · 54 MIN

Episode 2477: How Daniel Oppenheimer Learned That the Problem in his Marriage Was Himself

from Keen On America · host Andrew Keen

The writer Daniel Oppenheimer and his wife, Jessica, have been going to marriage therapy for many years. But, as he confessed in a recent New York Times magazine piece, he had to go to a superstar councillor to finally recognize that the biggest problem with his marriage was himself. Oppenheimer explains how renowned therapist Terry Real helped them, particularly by teaching him about healthy expressions of power. As with yesterday’s show with William Deresiewicz, our conversation expands to broader societal themes about modern masculinity, with Oppenheimer suggesting many men are now struggling with emotional maturity in relationships.Five KEEN ON AMERICA Takeaways with Daniel Oppenheimer* Self-awareness in relationships is crucial - Oppenheimer's confessional essay acknowledges his own reactive behaviors (anger, walking out, saying "f**k you") as primary problems in his marriage.* Men often struggle with emotional maturity - The conversation highlights how many men, including Oppenheimer, have difficulty processing emotions in healthy ways within relationships.* Power dynamics matter in relationships - Therapist Terry Real introduced the concept of "power with" versus "power over," suggesting passive men aren't effective in relationships, but dominating men aren't either.* Cultural representations shape expectations - Oppenheimer discusses how media portrayals of relationships (romantic comedies vs. train wrecks) create unrealistic relationship models without showing the healthy middle ground.* Good relationships require hard work - Despite 18 years of ups and downs, Oppenheimer and his wife chose to stay together, work through their problems, and find a path forward, suggesting commitment and effort are central to lasting relationships.Daniel Oppenheimer is a writer whose features and reviews have been featured in the Washington Post, Texas Monthly, Boston Globe, Slate.com, The Point, Washington Monthly, Guernica, The New Republic, Tablet Magazine, and Salon.com. He received his BA in religious studies from Yale University and an MFA in nonfiction writing from Columbia University. He lives in Austin, Texas, with his wife Jessica and his kids Jolie, Asa, and Gideon.Exit Right, which was published in February 2016 by Simon & Schuster, was his first book. His other book, Far From Respectable: Dave Hickey and His Art, was published in June 2021 by The University of Texas Press. It was reviewed in a variety of places, but the best review (ie the one that said the nice things most persuasively) was this one by Blake Smith.Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best known broadcasters and commentators. In addition to presenting the daily KEEN ON show, he is the host of the long-running How To Fix Democracy interview series. He is also the author of four prescient books about digital technology: CULT OF THE AMATEUR, DIGITAL VERTIGO, THE INTERNET IS NOT THE ANSWER and HOW TO FIX THE FUTURE. Andrew lives in San Francisco, is married to Cassandra Knight, Google's VP of Litigation & Discovery, and has two grown children.Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

The writer Daniel Oppenheimer and his wife, Jessica, have been going to marriage therapy for many years. But, as he confessed in a recent New York Times magazine piece, he had to go to a superstar councillor to finally recognize that the biggest problem with his marriage was himself. Oppenheimer explains how renowned therapist Terry Real helped them, particularly by teaching him about healthy expressions of power. As with yesterday’s show with William Deresiewicz, our conversation expands to broader societal themes about modern masculinity, with Oppenheimer suggesting many men are now struggling with emotional maturity in relationships.Five KEEN ON AMERICA Takeaways with Daniel Oppenheimer* Self-awareness in relationships is crucial - Oppenheimer's confessional essay acknowledges his own reactive behaviors (anger, walking out, saying "f**k you") as primary problems in his marriage.* Men often struggle with emotional maturity - The conversation highlights how many men, including Oppenheimer, have difficulty processing emotions in healthy ways within relationships.* Power dynamics matter in relationships - Therapist Terry Real introduced the concept of "power with" versus "power over," suggesting passive men aren't effective in relationships, but dominating men aren't either.* Cultural representations shape expectations - Oppenheimer discusses how media portrayals of relationships (romantic comedies vs. train wrecks) create unrealistic relationship models without showing the healthy middle ground.* Good relationships require hard work - Despite 18 years of ups and downs, Oppenheimer and his wife chose to stay together, work through their problems, and find a path forward, suggesting commitment and effort are central to lasting relationships.Daniel Oppenheimer is a writer whose features and reviews have been featured in the Washington Post, Texas Monthly, Boston Globe, Slate.com, The Point, Washington Monthly, Guernica, The New Republic, Tablet Magazine, and Salon.com. He received his BA in religious studies from Yale University and an MFA in nonfiction writing from Columbia University. He lives in Austin, Texas, with his wife Jessica and his kids Jolie, Asa, and Gideon.Exit Right, which was published in February 2016 by Simon & Schuster, was his first book. His other book, Far From Respectable: Dave Hickey and His Art, was published in June 2021 by The University of Texas Press. It was reviewed in a variety of places, but the best review (ie the one that said the nice things most persuasively) was this one by Blake Smith.Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best known broadcasters and commentators. In addition to presenting the daily KEEN ON show, he is the host of the long-running How To Fix Democracy interview series. He is also the author of four prescient books about digital technology: CULT OF THE AMATEUR, DIGITAL VERTIGO, THE INTERNET IS NOT THE ANSWER and HOW TO FIX THE FUTURE. Andrew lives in San Francisco, is married to Cassandra Knight, Google's VP of Litigation & Discovery, and has two grown children.Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

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This episode was published on March 25, 2025.

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The writer Daniel Oppenheimer and his wife, Jessica, have been going to marriage therapy for many years. But, as he confessed in a recent New York Times magazine piece, he had to go to a superstar councillor to finally recognize that the biggest...

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