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LABELED: Homeless Chic by Anna Dorn

I went to college in North Carolina where the girls have round faces and smile all the time. My face is angular and I hardly ever smile and I typically do what I want. I am not the Carolina boy’s ideal woman. But to be fair the Carolina boy is not ideal to me either. I mean, I like bros – they’re fun to drink – but I don’t want to have sex with them. I mean I will have sex with them – occasionally they’re okay at it – but I don’t want to date them. So in sum my four years in North Carolina were not the most romantic.

After college I moved to San Francisco mainly because I was over winter and wanted to smoke as much weed as physically possible. And when it came to dating I was pretty much in heaven. The Bay Area is one of the few places in the world where the men are consistently more attractive than the women (“earthy and unshaven” works better on men). Unlike the clean-cut pretty boys in North Carolina, the men were gruff and tattooed and edgy. And unlike the North Carolina boys who expect women to sit and look pretty, the San Francisco men seemed to care what I had to say. They liked that I wanted to be a writer and was generally sassy as fuck. And because the Bay Area is plagued by Peter Pan Syndrome, they didn’t mind that I wasn’t domestic and wanted nothing to do with a relationship.

I met Miles during one of my first weeks in San Francisco. He went to high school with one of my roommates and was over often. I lived with a couple from Craigslist – Molly, who owned apartment and paid the bills, and Adam, her younger boyfriend who did little aside from watch cartoons and hit his $400 bong. Molly and Adam had lived in San Francisco for years and had amassed a pretty cool crew. I thought all the boys were cute, but Miles was my favorite. He was tall and lean with black hair and piercing blue eyes. His face was pretty but he wasn’t a pretty boy. He had attitude and swagger and tattooed knuckles.

When I first met Miles, he was wearing a bedazzled green “R.I.P. Mac Dre” shirt. Miles, Adam, and I shared a bowl and discussed rap music. Miles was uneducated but smart. He had that depressed, jaded quality that I find irresistible. When he validated some likely inane point I made, I was smitten. We hung out a few more times and I felt some mutually flirtatious vibes. I learned that he had a “sort of girlfriend” which didn’t bother me because I’m drawn to the emotionally unavailable. After a few hangouts I received the following Facebook messages:

9/30, 5:02am

Miles Jensen

You have a new event invitation

to make out with me next time im at your house. if youre on your period its cool.

9/30, 6:54am

Miles Jensen


Adam wrote that msg to make me look like a creep. sorry.

Unfortunately Adam did not succeed in his efforts. While his message was genuinely creepy, I took it only to mean Miles was interested in me, which in turn made me more interested. And I like a man who isn’t afraid of the female period! Of course we were in weird territory because he was my roommate’s friend, but naturally as a 23-year-old I wasn’t thinking about the future consequences of my actions. Miles and I continued to flirt.

My sister visited San Francisco about a month after I met Miles. Naturally I wanted to give the impression that I was killing it in San Francisco, which I kind of was. Luckily my roommates had some friends over when she arrived. I walked to pick her up from the train station a few blocks away feeling buzzed. It was one of those rare warm San Francisco nights and the sky was that neon blue just before the sun sets. Olivia, my sister, emerged from the train and I gave her a big hug: “Olivia, I’m just so happy.”

When we returned to the apartment, Miles and his friend Clover were sitting on the couch: “Hey Hannah!” they said in unison. (My name is Anna.) I’d told them before I left that I wanted my sister to think I was cool, so they called me the wrong name to embarrass me, which I thought was kind of adorable, especially coming from Miles. I took Olivia to my room to drop off her bags. “Miles is my crush,” I told her. “Oh, he’s cute,” she replied.

Before returning to the living room, I had to briefly explain Clover, who I’d just met about half an hour before. “Fucking pigs, man,” she said when she walked in. She was a tiny white girl with black hair and feather earrings. She probably weighed about 75 pounds but had the self-assurance of someone much larger. Oh and had come to the apartment straight from jail – graffiti – with Miles and a bottle of whiskey. Miles and Clover had both been tagging the city for years; they were both at least 30, vestiges of the fading, pre-Google San Francisco. Within minutes I learned that Clover had been in jail numerous times, was raised by wealthy LA attorneys, and subsisted on very little. She was the prototype of an over-privileged delinquent, a type I know well.

I don’t remember much of what went down in the living room, likely because several cocktails and bong rips were involved. At around midnight, someone suggested going out. I had to wake up early for work, so I decided to stay in. But I encouraged my sister to go out. Perhaps a more protective sister would have discouraged this. My roommate and their friends were, as you may have gathered at this point, a bit sketchy. For one, they hung out with people who treated jail time as casually as a parking ticket. They had another friend who once tried to break into our apartment while we were all asleep – wasted, apparently with nowhere to go. And whenever I’d gone out with them in the past, we typically ended up in some seedy coke den.

While I don’t know what a lot of my friends do because I simply do not ask (snooze), I believe for the most part that they make their livings doing things are not illegal. I could not say the same for my roommates’ crew, which is fine, but perhaps they weren’t the sort of people I should be encouraging my younger sister to hang out with, without me, after midnight. But Olivia does not take well to being told what to do. “Good luck reigning in that thunder!” an ex of hers once said to me when I told her to put down an expensive looking vase she was balancing on her head at a house party. So I told her to go because I knew she would anyways. And she went.

They left and I curled up in my bed with headphones, my favorite buzzed activity after dancing and sex. I woke up at about 4 or 5 in the morning, cord wrapped around my neck like a noose, hearing a noise I at first assumed was coming through my headphones. I took off the headphones and put them on my bedside table, but the noise persisted. I soon realized I was listening to the sounds of fornication. It wasn’t Adam and Molly, but the voices were familiar. I soon realized, horrified, that one voice belonged to my sister; the other to Miles. I snatched my headphones and put them back on, but I could still hear them. I turned the volume up further, and further, but the noises persisted. At a certain point I couldn’t tell if I was hearing them have sex or the sounds were just persisting the way a cell phone continues to ring in your head even after it’s stopped. Regardless, I was furious and beyond uncomfortable. Hearing my sister have sex was bad enough, but hearing her do it with my crush was unbearable. I dug my headphones deeper into my ears, put a pillow over my head, and willed myself back to sleep.

I honestly don’t remember whether I confronted Olivia. I have a problem - or virtue, depending on how you look at it - where I physically cannot stay mad for more than an hour or so. So the night’s fury had dissipated by the morning, and when I met my sister after work, I mainly just wanted to know how her night was.

“Anna, last night was weird as fuck,” she told me. I knew that coming from a girl who once smuggled ecstasy for 10 into Mexico, this meant something. She said they didn’t really go “out,” but instead ended up in a dilapidated studio apartment where they did massive amounts of cocaine (surprise, surprise) and then Clover started tattooing people. “Clover called me a pussy because I wouldn’t let her tattoo me!” I could tell that even though she was complaining, Olivia had enjoyed the adventure. We shared a laugh and spent the rest of the weekend getting faded with Waspier, less sketchy delinquents. At the end of the weekend, we parted tired but on good terms.

I ended up hooking up with Miles eventually, after trying my best to erase the sounds of him and my sister having sex from my head. I can’t remember if we hooked up more than once, but I remember that he smelled to the point that I had to wash my bedding afterwards. I remember the next morning we shared a spliff and coffee on the balcony. He asked me if I was a Christian — obliviously his way of asking why I didn’t fuck him. I laughed and told him I just like to take things slow. He said that was cool in a condescending way and said it was cute that I wanted to be a lawyer in an equally condescending way. I think maybe we made out a few more times, but we never had sex. His pungent smell and the way he asked me if I was Christian caused my interest to wane. Eventually I started dating someone else and he started dating someone else and sometimes we would all hang out together in the apartment, everything copasetic.

At some point after we hooked up I casually asked Adam where Miles lived. He became quiet for a second before evasively responding that he was “between apartments.” Later I asked Molly and she laughed, before saying that he just lived wherever the girl he was sleeping with lived. So I’d hooked up with a homeless person! How bohemian. My friends will attest to the fact that even today I love to work into a conversation the “that time I dated a homeless person,” even if dating is a stretch.

I’m still friends with Miles on Facebook. Like many troubled individuals, he posts often, compulsively. While I stopped wanting to date Miles, I remain intrigued by him. So I know that he eventually got a job as a sign artist for Trader Joe’s and an apartment in San Jose. I know that he joined AA and became sober, but that recently he posted a picture of himself drinking a beer. I know that he and the girl he was dating broke up, but that she got pregnant and had his baby. While normally young parents who fill their Facebook pages with baby photos fill me with the urge to vomit, Miles’s child, Jagger, is pretty fucking adorable. And I’m happy for him. My homeless lover.

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