Former Redwood student’s gender transition from Lily to Miles

May 24, 2019

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Former Redwood student’s gender transition from Lily to Miles

Growing up as “Lily” for the majority of his life, Redpath made the final steps of transitioning to Miles after graduating Redwood in 2018.

Growing up as “Lily” for the majority of his life, Redpath made the final steps of transitioning to Miles after graduating Redwood in 2018.

Left photo courtesy of Miles Redpath. Right photo by Bella Roesler

Growing up as “Lily” for the majority of his life, Redpath made the final steps of transitioning to Miles after graduating Redwood in 2018.

Left photo courtesy of Miles Redpath. Right photo by Bella Roesler

Left photo courtesy of Miles Redpath. Right photo by Bella Roesler

Growing up as “Lily” for the majority of his life, Redpath made the final steps of transitioning to Miles after graduating Redwood in 2018.

After living the majority of his life as an inauthentic version of himself, former Redwood student, previously known as Lily Redpath, has recently come out as transgender. He graduated Redwood in 2018 and began his transition to Miles shortly after.


Redpath’s mother, Natalie Nesser, always supported Miles. She witnessed her son’s first signs of wanting to express himself as a boy.

“[Miles] was about two years old when she could finally tell me that she didn’t want to wear some of the clothes that I put on her. When she was first able to verbalize that she didn’t want to wear [dresses], I didn’t really know what it meant, I just knew that she wasn’t interested in the same kinds of things as my other daughter,” Nesser said.

According to Redpath, he never identified as a girl growing up. As soon as he knew the difference between boys and girls, he embraced his masculinity.

“When I was 10 years old, whenever I would hang out with my neighbors and guy friends, I would always find a way to play a game where they would call me a boy’s name,” Redpath said. “I was always just like, ‘I’m a little boy.’ I used to say to my dad: ‘Why do you have a penis, and I don’t?’”


As he entered the complicated world of middle school, he was increasingly exposed to uncomfortable situations.

“When I was in middle school, I was always uncomfortable in the girls’ locker room and in the bathroom. You go on those trips like Gold Country and I would always get called out in the girls cabins, like, ‘Why is there a boy in here?’ Everyone was always super confused, which made me feel confused,” Redpath said.

In eighth grade, Redpath discovered the meaning of transgender by searching the internet on his iPod. He never learned about the meaning of transgender in school, even during sex education.

According to Redpath, high school was challenging for him. It was a harsh environment for him to be himself, and he was too scared to begin transitioning there.

“I would be in the bathroom and people would walk in and walk out and double check the sign. I was just uncomfortable,” Redpath said. “I wish I had the courage to start transitioning in high school. Now that I have started, I always think about how it wouldn’t have been a big deal. But my mindset back then was a lot different.”

Aside from the passive aggressive commentary, Redpath experienced one major bullying incident in art class his junior year.

“[A freshman boy] would just make remarks under his breath like ‘choose your gender.’ I got so mad one day that I just beat him up. We both got suspended. That’s about the only time where it’s become an issue to the point where I felt like I had to act on it,” Redpath said.

According to Redpath, transitioning was in the back of his head through all of his high school years. It got to the point where he was always in bad moods because he felt uncomfortable in his own skin. After graduating, he finally took control and transitioned for his own health. In January, he started taking hormones. Later, on March 1, he got top surgery, a procedure performed on the chest as part of gender reassignment.


Graduating high school wasn’t the only thing that motivated Redpath to transition. His girlfriend Livie Mcleod, a senior at Marin Academy (MA), helped him make the first steps.

When Mcleod met Redpath, he was wasn’t out as transgender. They met at Mags in 2017, where they both work.

She first knew Redpath as a gay person presenting himself as a boy, which prompted her confusion.

“I was just like, ‘What pronouns do I use?’ This person seems to be expressing themself as a boy, but their name is Lily. As we got to know each other, I just got it and we started to know each other more as people,” Mcleod said.

When Mcleod became interested in Redpath, she started questioning her own sexuality. Unwilling to identify with the usual labels, she created her own.

“It was hard for me because I was like, ‘Am I bisexual?’ My sexuality became something that was really confusing. I’ve always been with guys. I like to consider myself as open-minded, because when we met, [Miles being trans] wasn’t something that stood in the way of me liking him,” Mcleod said. “I did see him as a girl for probably the first few weeks that we were talking, but it’s hard to know unless you experiment.”

When they began dating, Mcleod started adjusting to what made herself and Redpath comfortable, in part by determining relationship labels.

“I would never say ‘girlfriend,’ because I started to know what felt uncomfortable to him. [Saying girlfriend] started to feel uncomfortable to me. I was just his person,” said Mcleod.

According to Redpath, Mcleod helped normalize his transition and accept his true identity.

“[Livie] just made [the transition] feel a lot more normal. To me, in my head, it was so weird and different to be transgender,” Redpath said. “[She] just made me realize that it’s normal, and helped me accept it and be able to look at myself in the mirror and be like, ‘You’re trans.’ Before, I could never do that. She helped me a lot with getting myself to talk to my parents. I wouldn’t have done that without her.”

Photo by Bella Roesler
Redpath’s girlfriend, Livie Mcleod, has been one of his main supporters throughout the transition.

Mcleod experienced more bullying than Redpath during high school, as she was easier to target. Students at Marin Academy would make fun of her and say homophobic things.

“I really think that people were more scared to go up to Miles. Having [bullying] happen to me made me be open about [myself and my relationship], and be like, ‘This is who I am.’ I don’t even know who I am in that regard. But this is us and this who we are,” Mcleod said.

Mcleod and Redpath even got excluded from MA’s main pre-prom because students didn’t approve of Redpath.

“We went to prom, and the whole grade [at MA], a bunch of kids, were invited to this one kid’s pre-prom, and they just didn’t let us go. So we had a pre-prom with four of our friends because we were excluded and they didn’t want me there,” Redpath said.

Photo courtesy of Livie Mcleod
Mcleod and Redpath were excluded from Marin Academy’s main pre-prom in 2018, as students didn’t approve of Redpath. The couple ended up having their own pre-prom party with four of their friends.

The bullying eventually subsided when Redpath came out as trans.

“After I came out, no one really fucked with [our relationship] anymore. No one really gives [Livie] a hard time anymore,” Redpath said. “When you’re really confident about something, it starts to feel like the person who’s beating you down is losing.”


Redpath had been thinking of potential names for two years.

“The name was the hardest part. It’s like how are you supposed to pick that? You know, it’s like branding yourself. I had a list of names and [Miles] was always one that felt most comforting to me,” Redpath said.

The reason Redpath was able to finally make a decision on “Miles” was by trying out names with Mcleod.

“I went by Liam for two weeks and I didn’t really like that. [The name Miles] is really comfortable. I think about [my name] a lot actually, like maybe I want to do something else. It used to be such a big deal, like, ‘What’s my name going to be?’ But now I don’t really care as long as it’s not some feminine name,” Redpath said.

As a mother, Nesser had been calling Miles “Lily” for the majority of his life, and occasionally messes up.

“I slip up [with his name] a lot, and for a long time, I didn’t even notice that I made a mistake. I usually catch myself sooner now, like before I say Lily, I’ll stop and say Miles. But it’s still hard,” Nesser said.


“It’s been a process over the years discussing [transitioning], talking about taking hormones, talking about top surgery. I’ve always been supportive but I was also kind of encouraging him to be a little patient because it’s something very permanent, and you’re still maturing as a person. He never wavered on [the transition process],” Nesser said.

Redpath’s mother helped find Miles an endocrinologist, a doctor who specializes in hormones, as well as going to appointments with him. One of Redpath’s first steps was a consultation at UCSF’s Women’s Health Center, where his doctor is transgender herself.

“[The doctor] just asked me questions, like, ‘Are you sure you want to do this?’ [Trans doctors] always want to meet face-to-face, just because doctors who have been in that field of study just kind of know. They just catch the vibe,” Redpath said.

In order for insurance to cover his top surgery, Redpath had to get a letter from a therapist stating he had gender dysphoria, the condition of feeling one’s emotional and psychological identity as male or female to be opposite to one’s biological sex. Redpath went to see a therapist at a trans center called The Spahr Center, located in San Rafael.

For the duration of his recovery, Redpath couldn’t move his arms for one month. However, starting hormones proved to be easier. At his first consultation with the doctor at UCSF, he got his blood drawn and then went back a month later to start hormones. According to Redpath, the final step was making his transition known to the public.

“I posted a baby photo of myself on Instagram and changed my username. I was just like, ‘This is me now, respect it.’ I got 120 comments or something, from a bunch of my friends from high school and other people. The best part of it was getting comments from people that I just didn’t even think would be supportive, people who I thought would’ve been weird about it. They were showing me love and support,” Redpath said.


“How you get respect from other people is by being confident in yourself. Because if you’re trying to hide, [you won’t get that respect]. Don’t be afraid to be you. I’m so much happier now that I’ve done all of this. Yeah, I get weird looks and it’s scary, but at the end of the day, who’s happier? Me being me or you judging me?” Redpath said.

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