An exception to the rule: Barry Diller and Diane von Fürstenberg’s Jewish love story with a twist

Diller's memoir touches on many of Phoebe Maltz Bovy's interests: new Jewish books, pretty dresses, and the boundaries of sexual orientation.
Display of Diane von Fürstenberg's wrap dresses at LACMA in "DVF:Journey of a Dress"; 2014, photo by Bruce Monroe via Wikimedia Commons.

For convergence-of-interest reasons, the moment I knew there was an excerpt of Barry Diller’s memoir, Who Knew, available at New York Magazine online, I knew that this would be the subject of my next column. It is at the intersection of so very many of my interests: new Jewish books, Belgian-Jewish North American households, pretty dresses, and the boundaries of sexual orientation (the last of which is itself the subject of my own next book).

That’s the rational explanation. The real reason is that I am a nosy so-and-so and had always heard that Diane von Fürstenberg had a gay husband. I had not given this much thought, but once prompted, I was curious to know what was up with that.

The very existence of Who Knew suggests I’m not alone in my curiosity: “Much has been written about us, whispered about us, wondered about us. So I’ll just start at the beginning and let the story unfold.” Yes, I now plan to drop whatever I was doing and read the book once I have it.

***

Who are the people at the centre of this story? Diane von Fürstenberg, née Diane Simone Michelle Halfin, is a fashion designer. She invented the wrap dress. Even if you don’t think of yourself as a fashion person, you know these dresses.

She’s also just one of those iconic personalities always in the ether, even if you (like me) never gave her any particular thought. DvF, kind of like glamorous French-Jewish public intellectual Bernard-Henri Lévy (BHL) but with (even) better hair.

Barry Diller, for his part, produced Cheers and Saturday Night Fever, and went on to be an all-around mega-successful businessman in the entertainment field and beyond. Diller is, much like moi, of the Jewish persuasion.  

It is by no means a secret that Fürstenberg, the child of Holocaust survivors, is also Jewish. She and Diller were even featured in a Forward spread of Jewish power couples, in which I learned that they—like Barbra Streisandcloned their dog. But if the name “von Fürstenberg” failed to ping your Jewdar, this could be because it’s her married name. If you marry a German prince named Egon von Fürstenberg, you get to be a von Fürstenberg, should you so choose.

Of course, Ralph Lifshitz became Ralph Lauren without marrying any Egon von Lauren, and Calvin Klein just stuck with being Calvin Klein. For Jewish fashion designers, there’s no one path towards having your name on department store labels.  

***

It is generally assumed, when one hears that two people are a married couple, that these are people who have, or at least once had, an intimate relationship. That there are couples together for other reasons—companionate from the get-go—is indeed the stuff of whispers. The idea being that a couple’s secret is that they are not and never were involved in that way.

What we are looking at here are levels. A marriage, all things equal, is thought to be X. This marriage was guessed at as being Y. But it is in fact Z: a secret third thing.

According to Diller’s account, he and his wife are intimate. “I’ve lived for decades reading about Diane and me: about us being best friends rather than lovers. We weren’t just friends. We aren’t just friends. Plain and simple, it was an explosion of passion that kept up for years.”

But it’s not that he is a gaydar-pinging straight man, either, so the people who’d wondered, is Barry Diller gay?, they were also right, kind of: “And, yes, I also liked guys, but that was not a conflict with my love for Diane.”

It is my sense that female sexual fluidity is overstated, while male is underestimated. As in, for all the research and popular culture pointing to the idea that women are all basically bisexual, if you go out into the world, you will meet a whole lot of fully straight women, and a smaller but no-less-certain number of entirely lesbian ones. Women, that is, whose sexual and romantic interests are solely in men or in women. The notion that all heterosexual women are ‘a little bit lesbian’ is a straight male fantasy. (OK, also the fantasy of some gay and bi women.)

Men, meanwhile, are thought to be straight or gay. The popular imagination has little room for the existence of bisexual men, let alone men whose sexuality transcends labels. Apart from Jane Ward’s academic (yet spicy) monograph, Not Gay, there has not been a ton of exploration of male sexual fluidity outside lack-of-women-around scenarios.  

And yet there is Diane von Fürstenberg, whose first (royal) husband was openly bisexual, and whose current is… The Wikipedia page for Diller says that in the memoir excerpt, he “confirmed that he is a gay man,” but this is not how he describes it. What he confirms is that, in addition to his wife, he has been involved with men: “At that time the Europeans had a wiser attitude about this than us provincials. And today, sexual identities are much more fluid and natural, without all those rigidly defined lanes of the last century.”

This to me sounds like a man calling himself sexually fluid. He’s not denying he’s gay in order to claim he’s straight, but rather conveying that he’s not so easily categorized.

What I can’t decide is whether to look at this story, as he recounts it (it’s not like I know these people personally!), as modern, or as very much of another time.

***

Reading Diller’s account, I found myself wondering whether I’d have ever had the capacity to be so blown away by a Diane von Fürstenberg—by a glamorous, beautiful, captivating, jet-setting woman—that I’d have been able to transcend my heterosexuality and find a life partner outside of people I have the capacity to find attractive in that way. Would I have been able to make an exception?

That the answer was so clearly no led me to wonder what makes Barry Diller different from me. (Apart from business acumen.) Is it that he’s a little bit bisexual and I am not? Or is it about the difference between being a straight woman in a society that expects this, and being a quasi-closeted gay man in one that puts immense social (and legal, and economic) pressure on men to at least present as straight? Meaning: if I lived in a society where everyone demanded I partner with a woman, would I then have been able to round up however charming and interesting I found a woman platonically into something more?

Or! Does the fault here lie not (just) with homophobes of yore, but with, as Diller says, the rigidity of how male sexuality was and still is understood? The once-in-a-blue-moon bisexual, the man who mostly goes for men and likely identifies as gay, but the occasional woman makes the cut? The essayist Lauren Oyler wrote in Harper’s about having a gay boyfriend. Maybe this is just the world in its beautiful complexity! Even if this sort of rule-with-exceptions sexuality is more common among women than among men, there’s no reason to think such things would be absolute.

Is Who Knew a reference to those who did and didn’t know that Diller was into men, or more like, who knew he’d wind up falling for a woman? I will be reading to find out.

Where I land on this—not that it matters, not that I am responding to anything more than a famous person’s public writing—is that it’s likely a bit of both. It doubtless owes something to societal homophobia that Diller’s life partner wound up being a woman, when the pool of people he’s found interesting in that way did not have other women in it. But also, there are no shortage of gay men of Diller’s generation, including with social circles more conservative than Diller’s, who did not marry women. Maybe this is because their sexuality is less fluid, or maybe they just never met Diane von Fürstenberg.

The CJN’s opinion editor Phoebe Maltz Bovy can be reached at [email protected], not to mention @phoebebovy on Bluesky, and @bovymaltz on X. Subscribe to The Jewish Angle wherever you get your podcasts. We’ll have more updates on Substack and The CJN’s own daily newsletter.

Author

  • Phoebe Maltz Bovy headshot

    Phoebe is the opinion editor for The Canadian Jewish News and a contributor editor of The CJN's Scribe Quarterly print magazine. She is also a contributor columnist for the Globe and Mail, co-host of the podcast Feminine Chaos with Kat Rosenfield, and the author of the book The Perils of “Privilege”. Her second book, about straight women, will be published with Penguin Random House Canada. Follow her on Bluesky @phoebebovy.bsky.social and X @bovymaltz.

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