Hillary Thompson in Durham, NC

Skater Ladies Road Trip
4 min readJul 14, 2015

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Hillary Thompson, trans woman and skateboarder form North Carolina.

After seeing a feature written about Hillary from 2013 in Jenkem mag, I messaged her on facebook on the off-chance she would be available on the day I was driving through North Carolina and willing to do an interview. While she said she isn’t totally comfortable with all the attention she receives on the internet in recent years as one of the only out, trans, relatively high-profile skateboarders, she was kind enough to take time out of a hot Saturday afternoon to talk to me about her experience with gender identity and skateboarding over the past two decades.

Downtown Durham

I met up with Hillary at a skatepark, and from there we walked a few blocks to a low-key skate spot, locally dubbed “wallie street.” After some brief warm-up skating, we sat down to talk. Hillary started skateboarding when she was six years old, pushing around the streets of her suburban neighborhood. In middle school, she discovered street skating, 411 videos, and Alien Workshop’s Photosynthesis video, and immersed herself in the Durham/Raleigh skate scene.

A photo from Hillary’s facebook fan page.

In high school, confusion and uncertainty about her gender identity began to grow. When she turned to her parents for support, they sent her to a therapist whose philosophy with regards to gender was an outdated attitude that transgender folks have a “condition” that needs to be “fixed,” and essentially suppressed. Hillary sought a second opinion, and eventually found an experienced, reputable therapist who prescribed her hormone therapy and talked through a lot of the confusion and repression associated with growing up trans without a lot of information or support surrounding issues of gender identity.

I asked Hillary about the role of skateboarding in her life throughout her transition. She said it was definitely a constant, and that while she didn’t skate as much, it was always something she kept doing. However, she said that before her transition when she was prepared to give up skating in order to adhere to the gender norms of femininity. Before she transitioned, she felt intense social pressure to conform as much as possible to female norms, so as not to be “out” as a transgender person. She felt that if people saw her skateboarding, they would question her gender because, in the communities where she grew up, there are very few, if any, visible skateboarding women.

I asked her if she felt a difference in the way she is perceived when she goes to skateparks or skates at street spots since her transition. She said that at first it was difficult because she was working through a lot of issues of self-image. At the skatepark, she felt like everyone was looking at her, or thinking she was a freak. However, after more time working through issues of identity and self-image, she’s found greater confidence. She’s also found the skateboarding community to be overwhelmingly supportive. She says her current “skate friends” are people she talks with about anything and everything.

In her 20 years of skating, Hillary said she had only ever skated with one other woman, who had since moved to California, and couldn’t remember ever seeing young girls skateboarding. We talked a bit about the possible reasons for this, and I told her about all the support and community around girls skating I had seen in New York, and all the people I’ve been in touch with in California. She said her thinking is that, while Durham is a liberal city, it’s still in the south, and southern social attitudes with regard to gender norms have a real grip there. So perhaps theses social norms that say girls and women don’t skate go a long way to discourage them from every trying to learn. But Hillary’s own experience working through perceived social stigma at the skatepark could be telling of a more promising reality that skateboarders are actually supportive of all comers despite their intimidating facade.

I asked Hillary about her feelings towards her internet fanbase. Hillary has a facebook fan page with almost 7,000 “likes.” She said it’s definitely a weird part of her life. She talked about an internalized societal attitude that being transgender is not something to be celebrated, but rather suppressed or hidden. And so, it still weirds her out to receive so much attention and praise through the internet. She’s in the habit of declining most of the interview requests she receives in her facebook inbox. However, she said she will receive messages every once in a while from a young girl, or a young trans person, or a young queer person thanking her for showing them that girls, women, and people in the LGBTQ community can and do skateboard, and receive support for doing so.

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Skater Ladies Road Trip

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