Dana de Milo

January 29, 2023 Harper-Hugo Darling

Content note for police brutality, incarceration

“Nowadays I think that people still think they're alone and in those days you even felt more alone. You know, I had heard of Christine Jorgensen. [...] I would have been 6 years old when I read about it.

My mother asked me to set the fire, and I was crushing up the paper into balls and I came across this on the front page. GI swaps sex or changes sex or something, and had a photo of her with her hat on the side as a GI and a photo as a woman, I remember ripping it out, putting it in my pocket, and every night reading it under the blankets with a torch and thinking, well, I'm not the only person.”

– Dana de Milo

In the telling of history, certain names are linked together. This is the case for Carmen Rupe and Dana de Milo, two transgender women from New Zealand. In the later years of her life, Dana was often interviewed and quoted in discussing Rupe and their friendship, which has led to the story of Rupe eclipsing that of de Milo. But Dana, as a woman who ran away at 13 and lived openly as a transgender woman, is an interesting person in her own right and deserves more attention in the discussions of New Zealand’s queer history.

Born in 1946 in Aukland, one of the more notable facts about Dana’s life is how early she left home. She knew from quite a young age that she was a girl. Being the first grandchild in the family, she remembered a doting grandfather who died when she was quite young, but he knew that she was different:

“I was always like that. I mean, at three years old, my grandfather knew. He said to my grandmother, I was different.”

Unlike many other queer people in and before her time, Dana had some semblance of who she was and that there were other people like her out there. In an interview she would describe the first time she learned about transgender people, saying:

Dana would often dress up in women’s clothes and get a “hiding” from her mother as punishment. At school, she knew that her other classmates saw her as different and they put her down because of these differences. She tired of this treatment quickly and ran away from home with the help of family friends. Dana and her mother would later reconcile, and her mother would admit the punishments came from a place of fear that Dana would be bullied for who she was. Dana forgave her. In the note she sent her mother to restart contact and explain why she left, Dana would write:

“You know, mom, I've always been a sissy.”

Almost immediately after leaving home, Dana would begin regularly dressing in women's clothing, and she said of this:

“I thought, well if they're going to giggle at me, I'm going to bloody dress the way I feel. So I put on a dress from that moment on more or less.”

Though she had moved to the much more queer-friendly Wellington, things still weren’t perfect for Dana. Like many other queer people around the world, she found herself in trouble with the police. Throughout her life, she would describe being on the receiving end of constant police scrutiny and violent police brutality because of her gender. There were no laws against cross-dressing in New Zealand at the time, but that did not stop the police, who harassed her and made up charges to bring her in. This was not a unique experience, and Dana would warn against police as a general rule, saying that:

“If you're different, you don't go near a policeman because they’re God onto themselves.”

This, in addition to the poverty she experienced being a thirteen-year-old transgender woman, led to quite a few arrests. Often she was forced to steal to eat and survive, and she would end up in prison multiple times throughout her life. Thankfully, her experiences in jail were rather different than the usual narrative of a transgender woman in that environment, and she would go on to recall that the men treated her with exceptional care, saying:

“I always got a pack of cigarettes given to me. I got chocolate cake and coffee at night and all sorts of things through the window. I was spoiled in jail, very spoiled.”

She even remembered a time when she was sent to a harsher punishment and the men in the area would refuse to work until she was returned to her previous accommodations. These men were not alone in their treatment of Dana, and she was lucky enough to find a good amount of people throughout her life who supported her with full knowledge of who she was. While the prevailing knowledge in the medical community at the time was to keep transgender identities secret, Dana would outright refuse to do so, maintaining that anyone worth being in her life would be accepting of who she was. In contemporary times, this is accepted wisdom, but in the 1960’s it was a brave stance. It likely lost her friends and lovers; it also gained her close and honest relationships all throughout her life.

While she initially ran away from her home because of her mother, the two would reconcile and her mother would be a great support to her in her gender expression, attempting to help her get on hormone replacement therapy. Dana also had a close-knit set of friends who she would keep in touch with all throughout her life, some of her friendships spanning over 50-60 years.

One particularly notable friendship she had was with Carmen Rupe, who she was interviewed about quite a few times in the later years of her life. Carmen Rupe was a Maori drag performer, brothel keeper, and well-known transgender activist in the New Zealand community. Dana would work for Carmen in her cafe and nightclub for some time, and the two would maintain a friendly relationship up until Carmen’s death in 2011. Dana said of Carmen:

“You couldn't meet a kinder, more loving, generous person you know.”

But even with the supportive people she surrounded herself with, she was not part of a community that was unquestioningly supportive of her and people like her. In one interview, she discussed how gay men in specific would abandon her and other transgender women to keep themselves safe, saying of transgender women:

“We were the face of gayness, even though I wasn't gay [...]. But we were the face of gayness because gay men would run, and I might be at the party with them the night before, but they see you on the street, they're shot into the shop, they don't want to see you because they could hide behind the male clothes. Whereas, you know, we were the face of it. And we were the ones that got picked on. Unless you were overtly gay, then you got put down too, but if you could sort of, you know, if he was a guy that could sort of scramble up a bit, acting a bit Butch well, then they didn't get picked on. But if you were different, you got picked on, you know.”

Dana de Milo would persevere through, continually going to the medical community for some support in her gender journey, and the support that came was mixed at best. She would be on the bad end of many clumsy and bigoted attempts to understand transgender people by doctors, but she would not complain about her poor treatment for fear of getting in the way of another transgender woman getting support. When describing a negative experience that Carmen Rupe had in seeking gender affirmation surgery, Dana said:

“That's what we always used to think, we'd never say anything to these doctors that used us as guinea pig [...]. We never said another word with they even if they absolutely, you know botched us up is because we didn't want to step it up for another girl coming along. You always thought about your– your sisters that were coming along.”

Eventually though, after receiving continual impediments to her progress and rejections for silly reasons such as her height, she would decide to give up trying to get surgery and support at home. Instead, she went to Egypt. There was a particularly well-known doctor there that other transgender people she knew had gone to, and she would go to see him as well. Unlike the many other doctors she had met in New Zealand, this doctor was an accepting and supportive carer. Known as professor Beharry, he was entirely on Dana’s side when it came to her vision for her future, and would even say the surgery itself was not necessary outside of Dana’s own desire for it. She would describe him telling her this, saying:

“He said to me, ‘de Mila, there's nothing I can tell you. You're already there.’ I said what do you mean? He said ‘You are already there. This will be just a little, a little thing that will just carry you on your way.’”

This would reflect her own belief about her body, when being encouraged to take voice lessons by psychologists, she would say:

“I just want to change what's down there, I don’t want to change anything else, I'm happy with who I am.”

That being said, the surgery was a great moment for Dana herself, offering a change of mind as well as body. She later described this revelation:

“It wasn't until my change that I realized I'm not a dirty person. I'm a good person, you know, but it took 30 years, you know, till I was 30 to realize that.”

After receiving surgery at the age of 30, Dana would go on to live openly as a transgender woman in New Zealand for the majority of her life. Befriending and supporting other transgender women and queer folks of all kinds, she would work in sex work, as a waitress, dancing on the stage for a short time, and she would have a storied life full of unconditional support and love from the people around her.

Dana would die on February 12, 2018, at the age of 72, having lived a full and beautiful life surrounded by people who knew her and loved her for who she was. She is now mostly remembered as a bit of a side note in the story of the much more dramatic life of Carmen Rupe, but she was an interesting and valuable person in her own right, with a story that reveals a different type of life that a transgender woman could have. While her experiences were by no means always positive, she was able to live authentically and fully as herself, and people responded to that in a variety of ways. For some, it was violence, the police being a thorn in her side through the majority of her life, others reacted with derision. But many saw her for who she was and loved her for that. She would find and grow connections with both transgender and cisgender people throughout her life, and people from all walks of life found their way to her and built with her a legacy of community and support.

REFERENCES AND FURTHER READING

Disclaimer: some of the sources may contain triggering material

Congratulations Gareth on NZ Radio Awards Nomination – Gauge. (2014, April 9). https://ngataonga.org.nz/blog/sound/congratulations-gareth-on-nz-radio-awards-nomination/

Dana de Milo. (2017, November 3). Aunty Dana’s Op Shop. https://auntydanas.com/dana-de-milo-aunty-danas-transgender-op-shop/

de Milo, D. (n.d.-a). Dana de Milo. https://www.pridenz.com/ait_dana_de_milo.html

de Milo, D. (n.d.-b). Dana de Milo on Carmen Rupe. Retrieved January 29, 2023, from https://www.pridenz.com/ait_dana_de_milo_on_carmen.html

De Milo Dana. (n.d.). Tapatoru. Retrieved January 29, 2023, from https://www.tapatoru.org.nz/demilo

Wilton, C., & Taonga, N. Z. M. for C. and H. T. M. (n.d.). Dana de Milo [Web page]. Ministry for Culture and Heritage Te Manatu Taonga. Retrieved January 29, 2023, from https://teara.govt.nz/en/video/28841/dana-de-milo