Recently I stumbled onto a haunting old mystery I just had to share with my hopelessly romantic classic movie family.

In one of the few real bookstores left in New York, I was riffling through boxes of old postcards, looking for any from the 1939 World’s Fair, which I’m mildly obsessed with. I found one with a note on the back—from a woman to her brother, about a secret love affair. Sensing I’d come in on the middle of the story, I needed to know more! So I dug through every single box and pulled out every postcard from the Fair, and then asked if they had any more in the back. After sneezing my way through stacks of dusty boxes, I found a total of nine from the same woman!

All were written in a sort of frantic hand from Ann to John, telling him about this man she’s met. Below, I’ve typed them out in the order I think they belong in. The first two might be reversed though; it’s confusing because she mentions discovering his eyes are blue in the second one, but she mentions his name and sort of introduces him in the first one—and talks about his blue eyes there as well. Clearly she’s in a tizzy. I think we can all sympathize.

These were never sent as postcards; there are no stamps or cancellations. But Ann must have mailed them to John, perhaps in envelopes to conceal their contents—because in one, she mentions hearing that he broke his leg in a polo match, and how that would explain why she didn’t hear back from him.

John’s address is on one of them—and it’s in Beacon Hill. So they were society types. But Douglas, her secret love, lived in Winthrop, then a working-class fishing village.

Here is Ann’s story:

Dear John,

I’m in love it’s as simple as that and it’s one of the greatest things God intended us to have and to cherish. His name is Douglas and his eyes are blue.

Love, Ann

Dear John,

I met him again today and for the first time I realized his eyes were blue. Robin eggs blue. Let’s eat today at the most wonderful place in New York. Where’s that I asked. He shook his head, I don’t know but we will find it and I knew we would.

Love, Ann

Dear John,

What will mother think when she knows that her Ann has fallen for a man that never has appeared in the society column. Oh John we must never tell her.

Love, Ann

Dear John,

It rained to-day and so we went to the movies and saw Gary Cooper and Jean Arthur in “Mr. Deeds Goes to Town.” Douglas asked me to supper so I’ll have an awful lot to tell you.

Love, Ann

Dear John,

Mother arrived last night on one of her surprise trips. Of course Doug had to be with me. She wanted to know who he was and he didn’t care a damn who she was and said so. Oh come, I need you.

Love, Ann

Dear John,

Douglas has gone and I don’t know where he lives in Winthrop and besides I’m not so sure he went home. I must find him but mother watches me like a hawk.

Love, Ann

Dear John,

If you could only come and help me find him for now I realize I would never let mother stand in the way of our happiness but first I must find him.

Dear John,

I heard you broke your leg in a polo game. No wonder you couldn’t help me. Well John I visited the fair. I saw him but was unable to reach him. Perhaps I will see him again. It is my one last hope for tomorrow I leave with mother.

Love, Ann

Dear John,

I’ve seen him at last. He said for me to go home and that in August I must go to [she gives his address] and there I may see him and we will talk about what lies ahead for us two.

Love, Ann

There, maddeningly, is where the story ended—and the search began. I had the brother’s address and last name (a frustratingly common one), and Doug’s address, with no last name. I assume Mr. Deeds Goes to Town was re-released in sometime in 1939. (I thought maybe she meant Mr. Smith Goes to Washington, but that didn’t open until October.) So the movie reference didn’t give me much of a clue about when the postcards were sent. But Boston’s polo season starts in late May, so I’m guessing they were sent in June; if it were July, wouldn’t she have said “next month” instead of “in August”? That means Ann endured an agonizing couple of months to wait to see Doug again. What happened when she did?

 

He pored over Ancestry.com. He plowed into the Boston society pages on Newspaper.com. He dug and dug through all kinds of records, and now I know more about Ann than I know about my own family.

But first, the bad news about Douglas.

Dear Reader, she didn’t marry him.

It turns out Ann had plenty of reason to fear her mother’s wrath: these folks were Beacon Hill right up to their starched collars, complete with a household staff of maids, a cook and a nurse, with weekends spent racing yachts and attending cotillions. The year before her mad dash to the World’s Fair, Ann had debuted at the Tyrolean Ball, apparently to quite a splash.

 

But two years after her New York adventure, Ann, then 21, married a Yale man straight out of her own social set. They had two children, but eventually divorced. She later married a man nine years her junior (who, like husband number one, had a name so WASP-y it would make John Cheever blush). That was pretty daring at the time, especially in her traditional social circle.

 

But perhaps my favorite detail of everything Robert dug up was that Ann’s brother John—her co-conspirator, her confidante, the one she poured her heart out to about Douglas—was fifteen years old. Somehow I thought he was a wise older brother, but maybe he was just wise beyond his years.

 

Of Douglas, alas, we know nothing more. Did he and Ann meet again in August, as planned? I can’t bear to think he was a scoundrel. Did they reunite only to find that their feelings faded in the real world, away from the whirlwind of the Fair? Was the societal gulf too daunting? The Winthrop address almost hugged the shoreline, where lots of old brick boarding houses dotted the streets. Was Douglas a seaman or dockworker? Both were grueling, often dangerous jobs. Did something happen to him?

 

The rest of the story is destined to remain a mystery. I admit it didn’t end the way I hoped it would, but I still love Ann and her impetuous dash to the World’s Fair, with her worried (horrified?) mother trailing after her. And I love Douglas and his “let’s find the most fabulous place” joie de vivre. And I love them together, however brief their time was.

 

They may not have had forever. But they’ll always have Queens.

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• Tagged: 1939, beacon hill, boston, errol flynn, forbidden love, gladys cooper, new york world's fair, olivia de havilland, postcards