At 18, I left my conservative home in Charlottesville, Virginia, and went to Oberlin College in Ohio, where my housing lottery number landed me at Harkness Co-op, the scene of confusing sexual and romantic mores and practices: bisexuality always assumed, monogamy shunned, clothing optional. 

I was confused by all this but could hardly ask my parents for advice. Only decades later did I realize that the person I should have consulted was my great aunt Dorle, already in her mid 80s and peculiarly well-versed in complicated matters of love and sex.

She’d been married to Uncle Dario until his death a few years before, and I knew only fragments of her earlier relationships. 

I know that a man at Columbia Journalism School named Mowgli after Kipling’s “The Jungle Book” accused her of being a “demi vierge”—half virgin, when she wouldn’t go all the way. 

But all my assumptions about her exploded when I was tasked with clearing out her Midtown Manhattan apartment after her death. First, I had searched in vain for letters from the famous people she knew. Nothing from Maria Callas or Leonard Bernstein, though Benny Goodman and Diana Ross were in her rolodex.

Concealed under old newspapers inside a filing cabinet, I found hundreds of letters from a man named John Franklin Carter, who had been her lover for five years in the 1930s. 

“Dear Dorle, by one of those last-minute flukes which makes reason real, I am to be accompanied [by his wife] on my next trip to New York. I don’t think I’ve ever been so miserable in all my life.”

Continuing to scour her apartment, I discovered four other sets of love letters from the same era of her life. She met Carter, an FDR ally and journalist; Albert Coates, a conductor; and Bill Barker, a British policeman who commanded much of Mandatory Palestine, aboard ships, but I don’t know how she landed in the same orbit as J. B. S. Haldane, the famous British geneticist, and Georges Asfar, an antiquities dealer from Damascus responsible for the Damascus room in the Metropolitan Museum. 

No serial monogamist, Dorle once left Carter behind in America to meet Asfar in Damascus, hooking up with Barker along the way on a ship from Trieste, Italy to Haifa, Israel. 

And she was startlingly open with her lovers. Carter describes her journey to Damascus as “curing love with love,” and complains about “Mr. Asfar” and his “hashish cigarettes,” revealing that Dorle had told him her intentions. 

Later, Asfar complains that your “policeman in Palestine is quite assiduous in his correspondence,” and that “others too worry my heart,” as Dorle had also been transparent with him. 

He also admitted his own struggles with fidelity. “I confess to you, Dorle, that never before in my life have I enjoyed the pleasure of being faithful (even though it was relative faithfulness in the beginning)!”

Perhaps the revelations in the letters should not have been such a surprise. 

One evening, about a decade before Dorle’s death, I asked her an innocent question involving Uncle Dario in the 1970s over cocktails, only to learn that she couldn’t answer because he’d left her for an old lover in Rome.

“Go,” she’d told him, and “return when you can.” 

Perhaps she had learned from her own dramatic affairs that we can’t hope to keep our loved ones locked up with us if they desire to stray. We can only give them freedom and hope they return.

Thus Dorle imparted, after her death, timeless wisdom about relationships and intimacy. About the desires and sexual norms of a generation that has been labeled as prudish, its behavior—especially women’s—shaped by restraint and taboo. 

Born into a wealthy Orthodox Jewish family, she was slated to be married off young and serve her husband. But the collapse of the family business, a mismanaged bank on the Lower East Side of Manhattan, liberated her from all such expectations. 

The real lesson, though, that I think Dorle can provide us is the absence of absolutes. Despite all her love affairs earlier in life, despite her husband’s infidelity, Dorle had one of the warmest, most beautiful marriages that I have ever witnessed. Our lives can be long, if we’re lucky, and we can live them in different ways at different times. Leaving one man for another and hooking up with a third along the way in one period, steadfast and faithful in another, and a Penelope figure, calmly waiting for her husband to return, in a third. 

And in that gray area beyond absolutes, Dorle has also shown the existence among her generation of a mindset that might have lent itself well to candid conversations, an offering of valuable guidance and wisdom still valid today if only those of us in my own generation had known to ask. 

David Winner is the author of a fiction/non-fiction mashup, “Master Lovers,” and three novels, “Tyler’s Last,” “The Cannibal of Guadalajara,” and the Kirkus-starred “Enemy Combatant.” The story of Dorle and her lovers is detailed in “Master Lovers,” released in November 2023.

Is there anything that you don’t want people to see after you’re gone? 

What are you going to do to make sure that happens?

Send us your questions and comments and look for a more comprehensive article on what to do with your “stuff” in next month’s issue.