Dad as Wingman: Teaching Masculinity

Tom is a journalist and author. A former staff writer at GQ and Esquire, the film A Beautiful Day in the Neighborhood was based on his Esquire article on Fred Rogers. He’s currently a senior writer at ESPN, and his new memoir is called In the Days of My Youth I Was Told What It Means to Be a Man. It was an intense conversation — about dads, sex, Catholicism, and growing older.

For two clips of the episode — on being your dad’s wingman as a kid, and the dark secrets that Catholic families often carry — head to our YouTube page.

Other topics: his dad’s serious injury at Normandy; emulating leading men in Hollywood; selling women’s handbags; his extreme vanity and obsession with scents; “the first metrosexual”; women flocking to him; making Tom complicit in his countless affairs; how men benefitted from the early Sexual Revolution more than women; Vatican II; Tom’s close relationship with his Catholic mom; Tom fearing his dad; the friends who worshipped him like a celebrity; hiding his Brooklyn accent; hiding extreme porn and dildos in his briefcase that Tom found; sadomasochism and bondage; dad’s sleeping with both Zsa Zsa and Ava Gabor; a mystery mistress who spoke at his dad’s funeral; Tom’s grandmother who was a notorious adulteress in the press who pimped out Tom’s dad and his aunt; and the challenge of writing my own memoir.

Browse the Dishcast archive for an episode you might enjoy. We have some real stars coming up: Tiffany Jenkins on privacy in a liberal democracy, Adrian Wooldridge on “the lost genius of liberalism,” Jerusalem Demsas on the state of the left, Ben Rhodes on Iran and speech-writing, Harvey Mansfield on modernity, Daniel McCarthy on conservatism, HW Brands on the life of George Washington, John Gray on Trump’s new world, Bob Wright on the evolutionary force of AI, Stephen Grosz on the struggles of love, and Robby George on pretty much everything.

Please send any guest recs, dissents, and other comments to dish@andrewsullivan.com.