Dorothy Green. Photo by: Philana Woo

Dorothy Green likes to ride hands free, sometimes while standing on her pedals, cruising down the middle of empty streets. She’s the kind of cyclist who will zigzag into a packed car lane and chance red lights at a busy intersection. Her ride is a restored vintage blue Schwinn with yellow handlebars, her bag of choice a reflective fanny pack she slings across her chest, and her soundtrack—at the moment Australian post-punk—blasts from a mint green portable stereo she bought for $10. 

Her riding style reminds me of her standup comedy: combative, playful, haphazard. As she tells it, she used to do a bit where she picked a random man in the audience and started screaming, demanding he answer whether he would be able to fight the army of sons she planned to sire with multiple women. This was a few years ago, when she still lived in St. Louis and before her transition, when she presented as male. “I started being like okay, I’ll go to weird open mics as a weird skinny little eighteen-year-old and start doing what’s funny to me, and unfortunately what’s funny to me is just weird shit,” she said.

In a way, this is the Dorothy I know, the performance artist who likes to challenge strangers to a fistfight while simultaneously daring them to love her, or at the least, to acknowledge her. Dorothy is twenty-two and five-foot-ten; she has shoulder-length wavy hair with bangs dyed orange, and a Cheshire Cat grin. She speaks with the languorous drawl of an old Hollywood actress and chain-smokes like one as well. Her fashion sensibility is part hippie cowgirl, part riot grrrl. She captioned a recent Instagram selfie: “Goes to the goth night dressed like a slutty country bitch.”

I first met Dorothy at Open Produce, where she works. Open Produce is a compact grocery store two blocks from the apartment I sublet in Hyde Park. I had moved here from New York City in the middle of the pandemic to attend graduate school and missed late-night bodegas. Open Produce is open until 2am. With little else to do during lockdown, I found myself stopping in nearly daily, sometimes just to browse.

I looked forward to seeing Dorothy on her shifts, a few times a week and usually in the evenings. She posts a new handwritten index card by the register every shift she works; it bears the tagline “The clerk is a girl,” followed by a punchline. A classic one reads: “The clerk is a girl. She was also surprised when she found out.” Sometimes the vibe is sad: “The clerk is a girl. She’s already cried 3 times today.” Other times defiant: “The clerk is a girl. She’s wearing a dress + has a big knife.” I like all her index cards, but perhaps my favorite are the slightly wistful ones: “The clerk is a girl. If you keep quiet, she’ll stay like this forever.”

When my writing class assigned us to profile a local shop worker, I instantly knew whom I would pick. Like me, Dorothy moved to Chicago for school; she is studying journalism. She isn’t too keen on being labeled an artist, at least not when it comes to the pressure to create. “If I try to be pretentious, everyone will just figure me out to be dumb,” she says. “The art I used to make was directly related to the fact that I felt very uncomfortable in crowds.” She recently started a blog and is focused on relaxing and riding her bike for the summer.

The first time Dorothy and I sat down for an interview, in our respective apartments a few blocks apart via Zoom, was the first time we saw each other’s faces sans mask. That was about half a year ago. On this day, we are out for a bike ride. It’s been over a year since Dorothy started her transition. Her skin is glowing, and she is confident as ever. She wants to show off her body, to get trashed at dives and take Ubers she cannot afford home. This is her hot lesbian summer. 

We make a pit stop at Walgreens on 51st because Dorothy needs sunscreen for her delicate Irish skin. We lock our bikes together since I forgot my key and walk by a fried fish and chicken shop. I am hungry. We pass a busy nail salon, and for a split second I am surprised to see its Asian staff. I feel silly, like a cat fascinated by its own reflection in a mirror. After all, seventy-six percent of nail salon workers in the United States are Asian, according to the UCLA Labor Center. Still, we’d been riding through a predominantly Black part of the city and hadn’t encountered anyone who looked like either of us.

It occurs to me that this is the first moment of our ride off our bikes, interacting with other people. Whenever someone looked at us, I wondered why. Was it because Dorothy is white and I am Asian, because Dorothy is trans, or perhaps because we were cyclists? Did they assume we were affiliated with the university and thus gentrifiers?

Or maybe they weren’t thinking anything. As an Asian American, I’m used to having these thoughts of unbelonging. There’s a constant calculus that involves accessing my surroundings for potential hostility, the expected reaction to my perceived foreignness. The last time Dorothy was on a train, another passenger got up real close and asked her what she was as she gripped the knife in her pocket. Sometimes the hostility is imagined, sometimes it is unexpected, but always, it looms.

I end up buying sour cream and onion Pringles that I munch on while Dorothy slathers her face. We bike around some more, along tree-lined streets past churches and abandoned lots. On her blog, Dorothy writes: “Your body stops being a thing you’re self-conscious about and starts becoming a tool for you. It does what it’s told. Pedal faster, speed up. Don’t pedal, slow down. The only universal truths present in bicycling.” The temperature is in the seventies and slightly humid. All in all, a pleasant day for a bike ride.

Dorothy tells me a story about how she told off someone proselytizing downtown by the Bean. He called her a homosexual as she walked by with a friend, to which she replied, “At least I have better sex than you!” Her friend was mortified. Dorothy still likes to yell but there is a part of her that is demure. “I’m trans but I’m also annoying,” she says matter-of-factly. 

She is the genre-defying heroine of her own sci-fi novel yet to be written. I imagine her protagonist to be inspired by Cayce Pollard of Pattern Recognition (Dorothy’s been reading a lot of William Gibson lately), Kiki from the Hayao Miyazaki film Kiki’s Delivery Service (the story of a young witch who moves to a new town and a personal favorite), and Barb, the main character in Isabel Fall’s controversial short story “I Sexually Identify as an Attack Helicopter,” about a woman whose gender is reassigned to “attack helicopter” to make her a better pilot. We talk at length about Fall and how Dorothy wants to write about a mechanically enhanced character.

She recently reread The Chocolate War by Robert Cormier, a novel assigned by her Catholic high school that had a traumatizing effect. The story, which takes place in a Catholic high school, depicts students ganging up on an outcast who refuses to conform to its internal politics. The way Dorothy sees it, “It’s mostly about how it’s better to go with the herd, because if you dare disturb the universe you will end up getting beaten by a closeted gay kid.”

Dorothy has dealt with her share of rude customer interactions. She’s been heckled on the street. But she’s also reveling in her newfound freedom, cruising through the city on her bicycle in flowing dresses. “I think I dared disturb the universe at this point,” she says, before taking another drag.

✶ ✶ ✶ ✶

This is Philana Woo’s first piece for the Weekly. She is from San Francisco and arrived in Chicago via Honolulu, Beijing, New York, and Shanghai.

Join the Conversation


  1. Dot was all but run out of STL for being a serial sex pest and abuser. She has been called out for this more than once and rather than taking accountability, she just protects her tweets and deactivates her Facebook for a few weeks until it blows over. There is a ton of info available corroborating my claims here, but unfortunately it is under her dead name and I’m not going to include that here.

    If you are reading this, please think twice about including her in your scene. She is not safe.

  2. This is a really great concept, however it would be nice to hear from actual born and bread or longtime Hyde Park residents + community members… namely ones who are Black or who aren’t affiliated with the university. I promise, they exist! Most people with a university affiliation just forget about them/don’t consider them. Would also be nice to have someone who is actually from the South Side writing these types of profiles. That point of view is beneficial as this neighborhood and its surrounding areas have changes quite a bit (and very quickly) in the past couple of years.

Leave a comment

Your email address will not be published. Required fields are marked *