What my 99-year-old friend taught me about the joy of living

The first time Robina Asti opened the door of her New York City apartment to me, I was struck by how tiny she was. Her white hair was swept up in a barrette and her turquoise earrings dangled above her gently sloped shoulders.

Her slippers made a soft sound against the wooden floorboards as she padded into the living room of her Upper East Side apartment, which was filled with her late husband’s art, including a portrait of her next to an airport runway – a nod to her love of piloting planes, even at the age of 92. In another corner, a computer screen was ticking away with the prices of stocks she was keeping an eye on, a relic of her life as a trader.

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“So, what do you want to know about me?” she asked with the swagger and distinctive accent of the rare bird that is a native New Yorker. It was my first clue that her petite frame housed a larger-than-life personality.

The second came when she rattled off some of the places her nine decades on Earth had taken her: the Pacific theatre during World War II as a lieutenant commander in the United States Navy, Wall Street as the vice president of a major mutual fund and behind the makeup counter of a department store in the early days of her life as a woman.

But by far her favourite place to be was cruising thousands of feet above the Hudson River as a flight instructor, a pastime she still indulged on most weekends, despite her age.

I first met Robina in February 2014 when I was working as a reporter for Al Jazeera America. I had heard about her battle with the US Social Security Administration to receive widow benefits as a trans woman and had come to interview her. As she settled onto an antique red sofa embroidered with flowers, she picked up a photo of her late husband, Norwood Patton, as a young man and passed it to me with a cheeky grin.

“I’m sure the women chased him like mad when he was younger!” she laughed. “I’m very pleased with him. I loved that man.”

Robina’s love for Norwood was at the centre of her fight with the US government. The couple fell in love in the early 1980s and spent decades together before marrying in 2004. After his death aged 97 in 2012, Robina applied for the benefits she was entitled to as Norwood’s widow.

A year went by with no response from the government. Then, instead of a cheque, she received a letter in 2013 saying that her claim had been denied because she was “legally male” at the time of her marriage. All of her documents – including her Veteran’s Affairs card, pilot’s license and driver’s license – stated she was female. Robina was incensed.

“I lived my life as a woman,” she told me. “I am a woman.”

Up until then, she hadn’t spoken much about her transition, which she underwent in 1976, “at a time when prejudices were many times greater than they are today”. But the benefits denial lit a fire in her, and she contacted Lambda Legal, a nonprofit working on LGBTQ rights, for help. The group fought for Robina and won, and she received the Social Security benefits she was owed in February 2014.

“I checked my accounts on Valentine’s Day and there was a big bit of money in there, and I said, ‘Thank you, Norwood!’ It was a gift from him – and on Valentine’s Day, because that’s the kind of man he was,” she said. “All through our lives together, there was always that little sparkle from him coming forward.”

Robina’s life up until that point had been one lived quietly. She was born in New York City on April 7, 1921, and bragged that she grew up in Greenwich Village when it was still lit by gas lamps. She left high school at 17 to join the Navy, becoming a test pilot during World War II.

Few people outside her inner circle knew about her transition, and to the people in the apartment building she called home since 1965, she was just a sweet little old lady with an outsized laugh.

But speaking publicly about her battle with the Social Security Administration changed Robina. She realised that she had something very important to share with LGBTQ people struggling to find acceptance in the world: proof that things can get better with time. She began marching in the New York City Pride Parade, gave a Ted talk in 2016 and became a vocal advocate for LGBTQ rights in her 90s.

Studies have shown that the suicide rate among trans people is higher than the general population. Robina had credibility when she told young people life was worth living – she had found acceptance with her friends and with her mother, who was initially confused and upset by her decision. And she had experienced what it was like to exist in the depths of despair – and make the choice to keep going.

Robina’s decision to transition came after the death of her son, Pepe, in a snowmobile accident in Utah in 1972 when he was only eight years old. He died in his 12-year-old sister Coca’s arms, and Robina and her wife, Eva, were devastated.

“When my child died, I felt there was no way I could use that as an excuse to end my life, but I also couldn’t find anything to do that would justify my living,” Robina said. “I eventually came upon the idea of changing my life and becoming a woman.”

For the next three years, Robina began dressing as a woman in the evenings after coming home from her job as the vice president of a mutual fund.

“I would drive there and go to work as a man, and then I would come home at night and I would be a woman,” she said. It felt, she said, like “tearing myself apart.”

Robina longed to live her life fully as a woman, but the decision to transition was more than an emotional and physical one; it also meant leaving her lucrative finance job, which was not held by women – or trans people – in 1970s America.

“Because I had a pretty good salary out of that outfit, I wasn’t necessarily ready to give it up,” she said. “I needed the money, I had a child to raise and all of that. But finally, I just said, ‘I’ve had enough. I can’t do it any more, something has to change.’ So I quit and I became only a woman.”

When she told Eva about her decision to transition, “she was shocked, of course, but she acquiesced to it,” Robina said. Eva wanted to have another child before Robina transitioned. They had a second daughter, Eamonn in 1976, and then separated.

Eva “helped me, and indeed, she became my role model”, Robina said. The couple divorced in the mid-1980s but remained friends, and Eva, Coca and Eamonn moved to Florida.

That left Robina to begin “another great adventure” as a woman on her own in New York City. She lived alone in the apartment a block from the East River and went to work at the jobs that were available to women at the time: cleaning houses, selling cosmetics at Bloomingdale’s, working as a typist, cutting hair, “all of those kinds of menial jobs women were doing”, she explained.

It was a far cry from her big job at the mutual fund, but “I learned an awful lot. When you’re out working, you’ve got to hustle a bit, and you learn how to hustle,” she said. Her evenings were often spent listening to a friend play piano at a bar in her neighbourhood. It was there that a man caught her eye.

“One night, this man comes into the bar and he’s very properly dressed, and it was Norwood,” she said of their meeting. “He says he has … [an art] studio right down the street. We talked a bit and became quite friendly. We went out on a couple of simple dates, and I was beginning to like him.”

But Robina struggled with how to tell Norwood about her transition.

“It wasn’t too long before I realised this is make-or-break for me – either I tell him and he leaves, or I tell him and he stays,” she said. “But he was very upset because he never expected anything like this. So I said goodnight and I said goodbye, and I thought surely I would never see him again.”

“Within a week he came back to me and he said, ‘Robina, I love you. I don’t care. You are a woman, I never thought of you as any other thing, and I will never think of you as any other person.'”

The couple spent the next three decades together. Along the way, Robina found acceptance with her mother and with Coca, who had been 16 when she transitioned and struggled with it, unlike Eamonn, who had always known Robina as a woman from the time she was a baby. It was that acceptance that made Robina feel comfortable telling young LGBTQ people things can get better – because she had walked that path herself.

“”Don’t lose patience, no matter what they do. If they throw you out of the house, or kick you out forcibly, go – but don’t close the door,” she said. “Send a birthday card to your mother, send a card to your father, remember Christmas and New Year’s. If you’re Jewish, remember the Jewish holidays. And always, even if you know that they tossed it out or they sent it back to you, they know you sent them a card.”

Robina also came to love marching in New York City’s enormous, vibrant Pride Parade, including with Dru Levasseur, the lawyer who helped her fight for her widow benefits and became a friend. Seeing her beloved city alive with music and dancing and celebrating the right of every person to love whom they choose brought immense joy to Robina.

Robina and I stayed in touch over the years, and I had the chance to interview her about her remarkable life again. During one of our visits at her Upper East Side apartment in 2017, I confided in her that I was hoping to become a parent myself. She laughed and looked me right in the eye and said, “It’s the most beautiful and terrifying experience you can have, all at once, all the time.” She was right.

During the pandemic, Robina moved to California to live with Coca, reading, laughing, practising yoga and reflecting. She did not spend all of her time on the ground, of course: in July 2020, she set two world records as the oldest flight instructor and the oldest active pilot.

As her legacy project, Robina launched the Cloud Dancers Foundation with her grandson in 2019. Together, they set the ambitious goal of raising $100,000 to grant the wishes of LGBTQ elders. “I realise how invisible I am,” she said of growing old. “The acknowledgement of me as me is lost.” She hoped to give other people who had seen so much hurt and adversity in life an experience that celebrated them for who they are.

So far, the foundation has raised $10,000 and granted two wishes: one to an 80-year-old man to complete a surgery related to his transition, and another to fund transcription services for a 57-year-old man who is compiling the stories of transgender elders.

The last time we spoke, Robina told me how much she was looking forward to getting back to New York City and meeting my son, whom she called her “97 years younger new friend”.

Robina died in her sleep on March 12, 2021, less than a month shy of her 100th birthday. Whenever I am out running along the waterfront in the morning and see a small plane buzzing above the Hudson River, I pause for a moment and think of Robina and the advice she gave me: “Go live and enjoy it. There is joy in all of living if we see it in the right way.” Through her extraordinary life, she taught so many of us the joy of living as your true, authentic self – even if it takes decades to get there.