‘There were times I was a horrible friend’: How James and Olly kept their friendship alive for decades

A series of comings-out for City of Sydney deputy lord mayor Olly Arkins, 37 – the first trans woman to be appointed to the role – cemented a childhood friendship with events manager James Declase, 36.October 22, 2026 — 11:00amA series of comings-out for City of Sydney deputy lord mayor Olly Arkins (right), 37 – the first trans woman to be appointed to the role – cemented a childhood friendship with events manager James Declase, 36.James Declase (left) and Olly Arkins: “We’ve travelled the world together; we’ve been through heartbreak together; we’ve grieved together.”Brent LewinJAMES: Olly and I met in year 5 at an all-boys Catholic school in inner Sydney. Both of my parents were born in India and I was a bit of a nerdy outcast. Olly wasn’t interested in video games, Pokémon or Dragon Ball Z, but she didn’t quite fit in with everyone else either, so we kind of fitted together.In year 8, I threw a sleepover birthday party where we’d play video games and watch movies. Olly said point blank, “I don’t want to be seen at your party.” I was so upset by that and we didn’t speak for a couple of months. I think she was worried about being judged by the other kids for hanging with a bunch of misfits. We went to a high school where they’d say “You’re gay!” as an insult; they said it to me. Olly was probably thinking, “I don’t want to take that chance.”A few months later, I said, “I’m still hurt that you didn’t come.” She apologised and our friendship actually became stronger. We started to hang with the skater kids and, among them, were the two openly queer kids in our year. Olly wasn’t out at this point, but probably took solace in that. When she’d say, “I’m straight,” I’d think, “Well, that’s who you are then. Why should I say otherwise?” We trusted each other.When, in our early 20s, Olly called me one day to tell me that she was gay, I was thrilled for her. Later, she came out as non-binary. I remember us being at a music festival with two of our closest friends, Rosie and Holly, when Olly said, “While we’re here, do you reckon you can try calling me Olly?” then added, “I feel more comfortable being a woman.” I was like, “Yeah, of course.” And she has identified as a woman for the last couple of years.A while back, someone came up to her and said, “Why are you wearing a skirt?” I was like, “Why the f--- is it any of your business?” In those moments, I’m so protective. Why does my friend have to be subjected to that? I get so upset for her, even though this is her day-to-day. I hate that this is a reality of our society. On the flip side, she’s having an incredible impact. Olly recently told me about a beautiful interaction she’d had with a young trans girl, who – from seeing Olly now as deputy lord mayor – had wanted to meet her.Bless her beautiful ADHD brain, but Olly will often forget to respond to my texts, which does my head in. Lots of people want her attention now, but hello? Best friend over here! Eventually, she’ll be like, “Hi, I’m so sorry!” Then, “I’m here, I’m present.”Now she’s a high-flying deputy lord mayor and I have a young daughter, so we need to plan ahead, but the great thing is that when we’re together, it’s like nothing’s changed. I acknowledge that I’m a straight, cis, brown man; Olly is a trans, white woman. On paper, that doesn’t seem like it would make sense, but it does for us. We’ve travelled the world together; we’ve been through heartbreak together; we’ve grieved together. Why wouldn’t I support her in everything?OLLY: At primary school, which was co-ed, I’d often cry myself to sleep, wanting to wake up in the morning to a wardrobe full of girls’ clothes and to be able to wear the girls’ uniform. Later, at our all-boys school, the whole point of that environment was, “Give us your son and we’ll turn him into a man.” But the truth was, I felt no affinity with any form of masculinity.From day one, I was accused – rightly, I guess – of being gay. Those taunts weren’t necessarily even about sexuality: it was about gender-policing. Not acting like a man “should be” was social suicide. But with James, there was never any question that I couldn’t be myself around him.James was friends with the nerds and misfits and there were times when I was a horrible friend to him. I’ve got privilege in some aspects and could’ve been there for him as much as he was for me. We’ve had difficult conversations at points, but there was never a question that our friendship would end. James is an amazing human: so competent and capable and yet so unaware of his own talent and capacity.‘I’ve had many years of not living my life as myself out of fear … The fact that James defends me is beautiful and impressive.’Olly ArkinsWhen I told my mum I was gay, she started bawling, which I expected. Then I told James. There was no question that he was going to be anything other than excited and happy for me. Later, when I told Mum I was non-binary, she wasn’t that supportive again, but James always was.At the end of 2024, I was identifying as non-binary when I was elected as a City of Sydney councillor. I found myself sitting in the council chambers staring at my [former] name plate. I didn’t know if it fitted any more. Soon after that, James and I drove to the Strawberry Fields Festival [in NSW’s southern Riverina region] in a campervan with two close girlfriends. On the way, I was like, “Maybe we can try out a new name this weekend?” James was like, “Of course!”I’ve had many years of not living my life as myself out of fear. There are many times where I get comments about my appearance. The conversation’s either not worth it or you don’t have the mental capacity. Do I use this as an educational moment? Do I insist on being respected? From a safety perspective, it might not end well for me.The fact that James defends me is beautiful and impressive. It’s been helpful for [cisgender] friends to realise what it’s really like living as a trans person. I love being reminded of how many people are actually in my corner.James has had his different stages, too: his emo phase, his Dragon Ball Z phase, his bass guitarist era. The cutest thing is going over to his place now and watching his evening process: cooking and having dinner with his wife and daughter, playtime, bedtime. It’s the biggest transition that I’ve seen him make and he’s taken to it so easily. I think, “Wow, we’re not ratbag 20-year-olds, partying every weekend and sleeping in the same room. We’re adults.”From our partners