My Sexuality Is Not Loud and Proud — It’s Mine

My crooked path from lawyer to lesbian

Photo: Emilija Manevska/Moment/Getty Images

“Lesbian is irrevocably tied to failure in all kinds of ways.” — Jack Halberstam

“Latte thief,” Luis muttered while eyeing the butch woman who’d just stormed into the courtroom.

“Excuse me?” I asked.

It was 2009 and I’d just moved to San Francisco, mostly to smoke weed liberally following my graduation from college. I got an internship at the San Francisco Public Defender’s Office to please my parents and help me get into law school, and a nanny job for cash.

“Oh,” Luis whispered. “I haven’t told you about the latte thieves. They run this town — especially the Hall of Justice.” Luis was my boss.

“Huh?” I asked, not following.

“Shh,” he snapped; the judge was giving us a look. Luis and I worked in the research department, meaning we didn’t typically go to court, but today was the closing in a big murder trial and the whole office was watching. All the homicide attorneys were super hot, and this one was the hottest. His “trial name” — yes, like a stage name — was Phoenix Streets, and he rode a motorcycle blackout drunk every night.

The butch woman turned out to be the prosecutor. Stomping around in her boots (San Francisco Superior Court was very lax when it came to courtroom attire), she claimed the community would be in danger unless the accused was charged with the most serious charge on the indictment. Standard prosecutorial closing.

Looking back, it makes sense that law encouraged my straightness.

I don’t remember the facts of the case. By this point, all the rapes and murders were starting to blend together. It sounds callous to put it that way, but becoming detached was the only way I could survive. Otherwise, lawyers developed drinking problems or became violent themselves. It was a dark place, the Hall of Justice, but Luis made me feel safe, or maybe he just distracted me from all the madness. Really, he was my first California friend.

After the closing, while walking back to the office against a strong gust of wind, Luis explained the origin of the term “latte thief.”

“So a few years ago,” he told me, “this lesbian in a ‘Dykes for Hillary’ T-shirt stole my latte at Peet’s. It was very clearly my latte.” He was becoming red in the face, indignant. Suddenly his expression shifted to a playful grin. “I know a few women in the office who’ve stolen a latte… mostly in college… if you get my drift.”

Then my face turned red.

Luis often took me to expensive lunches and dinners. As a single, childless fortysomething who’d received a major payout on a recent lawsuit (he never told me the details), Luis was drowning in cash. He took taxis to work every day (this was pre-Uber) and often bought expensive French pastries for the office, which he never ate because he was always on a diet.

At one of our lunches, I confided in Luis that I too had “stolen a latte or two.” I was pretty uncertain about my sexuality at the time. I’d slept with a lot of men (what, like it’s hard?), but I’d also had a summer fling with a bisexual girl just before moving to San Francisco. It was in D.C., where I was living with my parents awaiting the West Coast move, teaching tennis to unathletic kids at a computer camp.

Like any emotionally stunted brat, I threw parties at my parents’ house well into my twenties. At the summer kick-off, I invited Emma the bisexual. She ended up being one of the last remaining guests. Dripping wet from the pool, I told her I was going to bed and she could sleep over if she wanted. This was not intended as a flirt, but more a polite gesture.

At least that’s what I told myself.

I went up to my room and immediately threw up in the toilet. Right after brushing my teeth, I got back in bed and Emma pounced on me. I’d made out with women before, but this was the first time my lesbian behavior wasn’t art-directed by lurky bros at a party. It was the first time I’d felt like a woman actually wanted me.

And I loved it.

“Have you done this before?” she asked.

“Of course,” I lied.

It was easy, though. I have a vagina, I know what feels good. Emma was very beautiful and theatrical when she came, a welcome relief from the revolting performance that is the male orgasm.

Emma texted me a week later to invite me to an underground rap show while I was at my camp counselor orientation. It was all very exciting; escaping my tragic suburban summer job to make out with a bisexual in a steamy dive bar bathroom.

Later that summer, at some basement dance party, this dorky man was all over Emma. I found it funny, the way he was trying so hard, completely oblivious to our flirtation. “Who is that?” I finally asked.

“Oh,” she said. “He’s nobody.” (They’re currently married.)

When I told Luis an edited version of this story, he assumed an empathetic expression and told me my secret was safe with him.

But back in the office that afternoon, Luis suddenly announced to a random group congregated in the conference room, “Anna told me she stole a latte!!!”

Luis was often shitty to me that summer, like when he made me write his briefs for him while he watched Deconstructing Harry in his office, or how he bragged about having once thrown a copy of the California Penal Code at a former intern’s head, or the multiple times he told me I needed to wear more makeup, or how he’d publicly announce that I was a lesbian in professional settings. But I could never be mad at him because I also loved him. He took care of me, and isn’t a roast the highest form of flattery?

Being left for a man with the charisma of a piece of toast, coupled with Luis’ constant tales of lesbian “brutality,” scared me straight for a while. Also, I couldn’t seem to find any lesbians that I vibed with. I don’t care about sports, or building things. I like my haircuts symmetrical, and my politics incorrect. My Great Experimentation of 2009 ended when a terrifying butch fucked me with a glass dildo that felt more brutal and less fun than any penis I’d ever encountered.

So when an old friendship with a femme boy from high school started to turn intimate, I leaned in. I won’t bore you with the details of my “straight period” (2010–2014), during which I dated three men fairly seriously, jumping from one to the next, often with some adulterous overlap. This was when I was seriously attempting to become a lawyer — working at the public defender and various criminal justice internships, going to law school, participating in moot court competitions and being a legal-writing TA, and even attending my graduation, despite my epic distaste for transition ceremonies.

Looking back, it makes sense that law encouraged my straightness. First, there was Luis, who treated lesbians like domestic terrorists. Then there was law school, where for three years I read court opinions stripping women of their agency, and where deviating from any kind of convention was a major no-no. If I were to be gay at Berkeley Law, it would have to be in a political way, like I’d have to protest or head an organization or something.

I resented the ego of the judges, particularly the histrionic alcoholic who made us listen to him rant for hours while he sipped bourbon as though his presence was a gift.

My only flirtation with lesbianism in law school was “Lesbian by Estoppel.” It’s not a real term; my friend Spencer and I made it up when we were drunk and studying for the bar — I believe it was Derivative Suit Day at BARBRI. The next day Spencer asked a friend who was studying for the bar in Texas if she had mastered Lesbian by Estoppel. Panicked, she said she hadn’t heard of it. Spencer went along with it for hours, explaining that the doctrine was likely prominent in Texas, as it was based on outdated assumptions about gender and sexuality.

We even created a Google Doc to define the term, which we eventually expanded into a larger document entitled: “Essential Principles of Lesbian Law,” alternatively “The Vagna Carta.” The terms are defined in outline form, the format we used to study for exams and the bar. Lesbian by Estoppel can be invoked when a woman claims a man sexually assaulted her. If the alleged assault survivor can produce sufficient prima facie evidence of lesbian tendencies, there arises a rebuttable presumption of lesbianism. Such evidence can include: 1) more than one pair of cargo shorts; 2) a Home Depot gift card; and 3) beyond de minimus welding or roller-derby experience. If the accuser cannot rebut this presumption, he is estopped from claiming that the woman acted in a heterosexual manner.

The Vagna Carta also defines principles such as “Dykeameralism,” “Bicurious Contracts,” “Lesbian Subject to a Condition Subsequent,” and “the Uniform Interstate Feline Support Act.” There are 26 terms in total.

My boyfriend at the time contributed significantly to this document.

My straight period and serious attempts to be a lawyer ended simultaneously, in 2014, when I moved to D.C. for a clerkship. If you use this word around lawyers, they’ll act impressed. But my clerkship was not prestigious. I worked for a pool of semi-retired judges in misdemeanor court. It was interesting but, as a brat, I resented working in a fluorescent-lit, windowless office for all the daylight hours. I resented the ego of the judges, particularly the histrionic alcoholic who made us listen to him rant for hours while he sipped bourbon as though his presence was a gift. I resented my cubicle-mate, Eva, who spoke in the vocal register of a small dog and did no work other than making constant unnecessary phone calls. I didn’t mind doing all her work for her, but I did mind that she never stopped talking to me, even when I radiated an unequivocal do-not-disturb vibe. On top of it all, I was living with my parents — at age 27, Juris Doctorate in hand, and no life to show for it.

Then came Tinder. Tinder was a shining light, a newish app promising a better life. My high school friend was swiping like mad one night at a bar, the first time I’d seen a normie act casual about internet romance. I downloaded Tinder the next night in my parents’ den, the same room where my dad used to smoke cigars. It was all wood paneling and fish-related art — very Boy, an aesthetic I protested by blasting Bravo, the network for women and gays.

Tinder’s routine registration presented a simple question: Are you interested in men, women? Without much thought, I clicked both.

I came across Nat’s profile that first night. She was wearing a silk black button-down in front of a white backdrop. Wispy bangs floated across her porcelain skin. She looked smart and angry.

I was smitten.

Before long, we were texting about Miley Cyrus’s Bangerz and Bravo’s Shahs of Sunset and literature. Nat had been the poet laureate at her college and was getting a Masters in cultural studies. She was taking an extra year to finish her dissertation on solitary confinement and had written her application essay about the Real Housewives franchise.

Swoon!

Our first date was eight hours long. We met on a Saturday afternoon at a dive bar — I ordered Fireball on the rocks — and ended up at a basement club, where we almost got hate-crimed. We were grinding to Missy Elliott when this man started charging at us out of nowhere. “Is that a chick?” He shouted in my face, pointing toward Nat. Some of his friends rushed over and held him back.

It was all so exciting!

On Christmas day that year, my mom cornered me in the kitchen. “Is there anything you want to tell me?” she asked.

“Um, no?” I said. My mom isn’t one to ask personal questions. She’s a distant Libra, a WASP. Interested in my outfit and my job performance, but not my emotional life.

“Are you dating anyone?” she asked.

I swallowed hard and said nothing. She’d never asked me about my dating life before.

“You know I support you no matter what,” she said. She was being really creepy. It was starting to feel like the Hollywood version of a coming out scene, a narrative I deeply resent. (Perhaps I’m abnormally resentful.) There’s something fascist about it. Like, “Announce yourself, witch!” No thanks. My sex life is nobody’s business but the select few to whom I compulsively overshare — and not in a dramatic “I’m gay” way, but more like, “Ugh this bitch is ruining my life!!!”

Maybe my mom had overheard me overshare.

“Yeah,” I said. “I’m dating someone.” I told her about Nat in about as few details as possible, but was sure to include that she was a graduate student at Georgetown.

“You know,” she said, eyeing the toast she was buttering, “… it would be much easier for everyone if you dated a man.”

While I was happy that the conversation hadn’t taken the corny turn I’d feared, I was still upset. Not because my secret was out — it was never really a secret anyway — but more because I was losing control. Of what, I wasn’t entirely sure.

A year later I was back in California, working for a criminal justice nonprofit and going HAM on Tinder. (Nat and I had long broken up, opening my lesbian Pandora’s box.) One afternoon, my mom called because she “needed help finding a psychiatrist.”

I was surprised. When I’d recommended therapy in the past, she typically expressed fervent skepticism of the entire mental health profession, or told me about her former psychiatrist who had died.

“What’s going on?”

“Well,” she uttered with caution. I pictured her searching for the right words.

“You.”

“What?” I’d asked. She was silent for a while.

“Why did you send me that article?”

I paused to think. I didn’t recall sending her anything. “What article?”

“The one from that website,” she said, “there’s a picture of you at the beach.”

Fuck.

“I didn’t send you anything on that website,” I said, pushing down my panic.

The way my mom talks about my career is similar to how she talks about my sexuality. I am meant to be a lawyer just as I’m meant to be straight.

At the time I was writing personal essays under the pen name “Margot Fontaine” for a now defunct website which no one read. My editor would send me an email whenever someone left a complimentary comment on one of my posts. I sent one nice comment to my mom to show her I wasn’t delusional for pursuing writing, which she’d implied on numerous occasions — once comparing me to a “basket weaver.”

I thought I was careful to include only the comment, without any reference to the article or website. But I’m not the world’s most careful person.

“There was a link,” she said, “when you sent me the comment.”

“Oh,” I said. “I never meant to send that to you.” I swallowed hard, afraid of what was to come. The article was called, “It’s Raining (wo)Men.”

“Well I was horrified,” she says, voice steady but tension brimming, obvious even from 3,000 miles away. “Anna, did you really steal a mink?”

I couldn’t help but laugh, only for a second, at the fact that this was the detail that gave her pause. In this same essay, I had written about consuming amounts of Adderall that “would make Lindsay Lohan jealous.”

“Anna,” she said, voice beginning to shake, “You stole someone’s mink coat?”

“‘Borrowed’ is a more accurate word,” I explained. I said that my writings were loosely inspired by actual occurrences, and that the characters in my stories — myself included — take on lives of their own, once my fingers start to hit the keys.

Her responses were expected:

“Your subject matter is frivolous and disturbing.”

“You come off as a psychopath.”

“You’re throwing your life away.”

“You sound… unwell.”

The way my mom talks about my career is similar to how she talks about my sexuality. I am meant to be a lawyer just as I’m meant to be straight. It doesn’t matter that I spent my childhood writing stories and never felt particularly drawn to men. Quitting law and dating women ended the same way: failure.

Not only am I gay (automatic letdown), but I’m the wrong kind of gay. In fact, I’m not even convinced I am gay. I’m indecisive, flexible, a Kinsey 3.4, queer — a word that originally meant “freakish.”

As far as those in power are concerned, the right way to be homosexual involves falling into heteronormative patterns. For a femme woman, it involves partnering with a butch, who will perform masculinity with varying degrees of success. It involves “U-Hauling,” or becoming emotionally attached to your lovers hard and quick, falling into domestic patterns that resemble the nuclear family. It involves being grateful that the Supreme Court gave gays the right to marry, and listening to activist singer-songwriters. It requires being “loud” and “proud.”

It does not involve harboring romantic fantasies about being a closeted lesbian fashion icon in the ’70s, marrying a gay man, and being free to fuck around at my leisure. It does not involve feeling nostalgic for when marriage was a strictly heterosexual institution. It does not involve wondering whether you began dating women because you were bored, or as a subtle dig to capitalism or to your parents or to expectation, or because you were unstable, unconcerned… unwell. It does not involve viewing sexuality as a meaningless preference as opposed to an expression of identity.

It does not involve having more Shame than Pride.

Despite that I’m now living my “personal truth” — full-time writing and dating exclusively women — I still sometimes miss being in law school with a boyfriend. Not because I was happier (whatever that means), but because existing was frictionless. When I met strangers of any age, I always had the perfect answer. I was on the path to success, and dating a hetero who would go on to make loads of money in Silicon Valley. Dan Savage doesn’t take into consideration the psychic toll of being a failure. Your “personal truth” is a neoliberal myth, a favored concept of marketers and people trying to sell you things. It doesn’t exist in a vacuum.

I think I was drawn to Luis because he treated my sexuality as a joke, which was vastly more comforting than the grand reverence society had recently decided to give it.

And whenever society gives something reverence, my immediate instinct is to demystify. Maybe it’s my purpose.

My best friend from law school, Alice, started working at the San Francisco Public Defender after we graduated. On my 30th birthday, Luis texted me:

I heard from your spy (Alice) that you are doing extremely well. That’s all that matters. And you are not old. I would love to change places with you. I, on the other hand, am constantly under threat. I’m actually working in the Peet’s Coffee where my latte was stolen. My psychiatrist thought I should confront the horrific memory by spending time at Peet’s. Life is full of many challenges. We all have our crosses to bear.

Luis had been writing a latte-thief-inspired novel since I met him, and in my response, I asked him about it. He said he was taking his time, expounding, “It started out as a comedy but it had taken a turn to the horror genre.”

At the time, I had dated a very mean woman and experienced the horrors of lesbian Tinder. I said I understood.

“They are not much different from grizzly bears,” Luis responded, “I’ve been watching multiple documentaries on grizzly and polar bears. Apparently, these bears have similar mating habits as the latte thieves.” There were two spaces in between all the sentences in his texts, as if he were writing a brief.

How so?” I asked.

“The sheer brutality of the act and the horrifying groans. Latte thieves also fight with other latte thieves in order to mate with the woman of their choice.”

His behavior reminded me of writing the Vagna Carta. Like, it’s my rules now.

I said this didn’t really resonate with my own experience. The performative moan, I thought, was better suited to heterosexual intercourse, in which men expect a porny soundscape. Being territorial also seemed more masculine than not.

“There are always exceptions to the rule,” he texted back, “You are probably a panda bear type.”

I asked him what that meant.

He said he didn’t like to generalize, but could admit that some latte thieves are neither aggressive nor scary, like a panda bear. Who doesn’t like a panda bear? Everyone does.

He kept typing before I could respond, Go get a latte and enjoy this beautiful day!”

In The Queer Art of Failure, Jack Halberstam writes that there is “something powerful in being wrong, in losing, in failing.” I didn’t identify it as such at the time, but I admired Luis’ refusal to conform to society’s rules. He didn’t date or have kids, and he wasn’t ashamed about either. He defended criminals for a living. He wasn’t PC or woke. He would wear sweatpants to work and then change into a suit with his door open when he “had to talk to the boss.” He spent all his free time at the Jewish Community Center, despite being Catholic. His behavior reminded me of writing the Vagna Carta. Like, it’s my rules now.

Law’s main operating premise is, “It has been this way so it shall remain this way.” The law has a lot of reverence for the past, for convention, for predictability. But life isn’t predictable. We’re spinning in space! And no one knows why.

Life is arbitrary. There is no “reasonable man” — a standard found all over the law. People are mostly irrational, and when it comes right down to it, we follow our own laws.

Names changed for privacy.

Anna’s debut memoir, Bad Lawyer, will be published by Hachette Books in Spring 2021.

vagablonde (unnamed press, may 2020); bad lawyer (hachette books, spring 2021)

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