In this episode we talk about gay men and women: friendships, commonalities, and the often overlooked sexual tensions. We’re joined by Phoebe Maltz Bovy, who deals with some of these issues in her book, The Last Straight Woman: On Desiring Men, from bachelorettes at gays bars to straight girls on Grindr to the women who fall in love with their gay besties. We talk about how some of these themes appeared in the past, in Christopher Street, and also how Phoebe uses them in her book to think about our cultural understandings of gender and desire. We talk about some famous intellectual straight women who were problematically horny for gay men and some gay men who were oblivious to the fact that their women friends were horny for them. We recover the core commonality that gay men and straight women have—being horny for men—and note how new cultural ideas about sexual fluidity and queerness mistakenly suggest that gender doesn’t matter in who we desire, leading to discourses that are strangely detached from reality.

Chapters

(00:00) Introducing the last straight woman

(08:40) Being bloggers and bad grad students

(12:39) Gay men and straight women in Christopher Street

(20:55) The fake lesbian straight woman who got Me Tooed

(24:18) Are straight women and gay men really platonic friends?

(31:39) How we came to think all women are queer

(37:34) Phoebe’s concept of “frumpy but horny”

(43:02) Are that many people really bisexual?

(59:38) You can’t figure out your identity online

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Phoebe Maltz Bovy is an editor at the Canadian Jewish News and a columnist for the Globe and Mail. She co-hosts the podcast Feminine Chaos with Kat Rosenfield and writes on Substack. Her new book, The Last Straight Woman, was released in May 2026.

Mentioned

• Seymour Kleiberg, “Friendship: Gay Men and Women,” Christopher Street, October-November 1979.
• Phoebe Maltz Bovy, The Perils of “Privilege”: Why Injustice Can’t Be Solved by Accusing Others of Advantage (2017).
• Blake Smith, “The Ethics of Self-Interpretation,” Tablet, November 18, 2024.
• Melissa de la Cruz and Tom Dolby, Girls Who Like Boys Who Like Boys: True Tales of Love, Lust, and Friendship Between Straight Women and Gay Men (2007).
• Randall Jarrell, Pictures from an Institution (1954).
• Zoe Greenberg, “What Happens to #MeToo When a Feminist is the Accused?” New York Times, August 13, 2018.
• Rachel Aviv, “Martha Nussbaum’s Moral Philosophies,” The New Yorker, July 18, 2016.
• Rachel Aviv, “Agnes Callard’s Marriage of the Minds,” The New Yorker, March 6, 2023.
• Cartoons Hate Her, “I Dress for My Personality, and My Personality is Annoying,” June 16, 2026.
• Avital Ronell, The Telephone Book: Technology, Schizophrenia, Electric Speech (1989)
• Phoebe Maltz Bovy, “Lena Dunham’s Frumpiest-Horniest Scandal, Revisited,” May 13, 2026.

Down with corporate Pride! Pride is a protest! Stonewall was a riot! Pride month has become as much about social media discourse as anything else, and in this episode, we try to look beyond posturing slogans and history-distorting morality tales to confront the many possible meanings and feelings one might have about Pride. We read Andrew Holleran’s 1984 Christopher Street essay, “We Must March, My Darlings,” which suggests a cultural politics of Pride that preserves it as an annual ritual with shifting audiences and meanings, one that need not always be stridently political but which can gather a solidaristic charge in particular political moments.

Chapters
(00:00) Intro

(03:34) What we’re doing for Pride

(05:40) David’s ex-wife took his first Pride photo

(10:18) Twitter gays trying to improve Pride discourse

(14:31) Andrew Holleran’s Proustian Pride essay

(23:59) Blake’s high horse about Bernie Sanders

(29:11) How “normie” gays feel about Pride politics

(36:01) Who is Pride addressed to?

(43:00) Why Holleran is a deeply political writer

(52:00) Bernie and David’s crisis of being a left intellectual

(55:00) How 2020 rewrote the Stonewall narrative

(59:43) Why gays being “normal” is what we’re fighting for

Sources

• Andrew Holleran, “We Must March, My Darlings,” Christopher Street, November 1984.
• Walt Whitman, “Pioneers! O Pioneers” (1865).
• Lillian Faderman, The Gay Revolution: The Story of the Struggle (2016).
• Andrew Holleran, “In the Age of Christopher Street,” Gay & Lesbian Review, May-June 2026.
• Carmen Maria Machado, “What Does Pride Mean Today?” New York Times, June 16, 2020.
• Andrew Sullivan, “How the Gay Rights Movement Radicalized and Lost Its Way,” New York Times, June 26, 2025.
• David Carter, Stonewall: The Riots that Sparked the Gay Revolution (2004).

We’re drowning in algorithm-optimized relationship slop, social media sob stories about the supposedly toxic gay dating scene, and ragebait on worn-out subjects like monogamy vs. open relationships. It can feel surprisingly hard to find real gay men talking honestly about what it’s actually like to be in a relationship. Even in the history of gay writing and thinking we talk about on this podcast, it’s easier to find depictions of sex, yearning obsession, or doomed love than of two men figuring out what it means to be together.

In this episode, we talk about one exception to the rule: A groundbreaking 1978 feature in CHRISTOPHER STREET that interviewed two men, Philip and Neil, about the drama and power dynamics of their relationship. The article included the beautiful—and sexy—photos they took of each other while they were together. We revisit Philip and Neil’s story a half-century later as a springboard for talking about our own relationships and experiences, and cover topics including:

• How sex is different in a relationship vs. as a single person
• How sexual positions and gender expectations shape gay relationship dynamics
• What’s unique about the male-male couple
• How gay lovers are different than gay friends
• What you should NOT talk to your boyfriend about

Chapters
(00:00) Why love is a perfect topic for Pride
(06:50) A groundbreaking look at a gay couple
(22:27) Philip and Neil’s images of each other
(30:10) Cruising and hookups vs. relationship sex
(42:24) How neuroticism and overanalysis kills desire
(48:00) What’s unique about the male-male couple
(56:44) Boyfriend twins, similarity, and competition
(01:04:34) Sexual attraction vs. common interests
(01:09:54) How we decided Philip is the villain
(01:17:32) Should your partner be your "best friend"?
(01:22:44) Sometimes your feelings are boring and stupid

Sources

Michael Denneny, Philip Gefter, and Neil Alan Marks, “Anatomy of a Love Affair,” Christopher Street, February 1978.

Michael Denneny, Lovers: The Story of Two Men (1979).

Michael Denneny, Decent Passions: Real Stories About Love (1984).

Adam Mars-Jones, Box Hill (2020) and Waters of Thirst (1994).

Renaud Camus and Farid Tali, Incomparable (1999)

Jackson Davidow, “Two Lovers,” The Baffler, September 7, 2023.

Adelle Waldman, The Love Affairs of Nathaniel P. (2010).

Pillion, directed by Harry Lighton.
Don Jon, directed by Joseph Gordon-Levitt.
Annie Hall, directed by Woody Allen.