A Riff Gone Too Far: Jess and Tom

I put on this dress this morning. It’s a modest, sleeveless, black maxi with a blue and purple floral print that looks sort of like watercolor. When I say “this morning,” I mean just about 10:45 AM—not my best, not my worst. Late summer depression has held me tenderly in its grip this year, and anything before noon feels like a win—a win that I tend to celebrate with my daily Facetimes to my just-about-as-depressed-as-I-am friend, Kate.

Kate congratulated me on managing to get dressed (minutes earlier, when I had called for a clearly premature victory lap, I had still been in bed, unclothed; only when she had to hang up on me to get her bagel delivery did I take a cue that it was about time to arise). As trans women may be wont to do, we fell into a dissection of the dress I had chosen. For a variety of reasons, it’s not difficult for us (Kate and me, but perhaps other trans women, too) to fixate on how our choices of personal presentation may affect how the world perceives us: what kind of woman wears this dress? What signals does this dress give to an observer? Where in a complex matrix of archetypes of femininity does this dress place me? How do I succeed and fail to embody those archetypes, and what impression does my combination of gendered successes and failures leave on a passerby?

We arrived at: elementary school art teacher, but hot. She’s not outright slutty, but she certainly knows how to flatter herself. The dress is full length, shows no leg, and doesn’t cling, but the fabric does hang delicately on her frame, and the length does wonders for a willowy gal. What’s more, it’s back-to-school, parent-teacher conference night, and around now, at the top of October, she rocks the last breaths of a Cherry Grove tan on her bare arms. Paired with some rose quartz beads and a playful little shawl that just won’t stop slipping off her shoulders, the overall effect is very sweet—perhaps a bit eccentric, edging on disheveled, and pretty, to be sure, but a far cry from femme fatale. And yet, a ring is conspicuously absent from her finger, and the Board of Education’s decision to hire a trans woman at an elementary school was not announced to zero stir among parents. This school district is maybe a blue-leaning purple suburb, full of tolerant folks who largely describe themselves as “the least prejudice [sic] people you ever met,” but around kids? NIMBY hackles have gone up, and many families have been forced to reckon with where they stand on this whole transgender business, in a very real way that feels different from the theoretical arena wherein they typically consider the matter.

Beyond that, this lady looks nice, in a way that has disarmed Jess and Tom, a married couple of thirty-somethings sitting at children’s desks at back-to-school night. See, the American imagination has a way of reducing trans women to sexual extremes: bombshells who exist as a porn category, or sexless oafs to whom the correct response is pity and polite indulgence in their “she/her” thing. Mainstream discourse has done little to prepare Jess and Tom for this more common reality, that this trans woman is simply a person living her life. Sure, she might like to be thought of as attractive and worthy of love, but no more or less than anybody would. And certainly, single and approaching thirty, she’s in the habit of presenting herself as someone who could conceivably catch an admirer’s eye. But mind you, she’s at work, as an elementary school art teacher, so the primary consideration for her dress choice was to strike a balance between professionalism, warmth, and approachability. She’s the person who teaches techniques to paint sunflowers and won’t bat an eye when they come out like lemurs. “I love them,” she always says.

But, still, she’s just friendly and put together enough to unmoor Jess and Tom. Regardless of presentation, a trans person’s very presence, intentionally or not, presents a challenge to their straight worldview. Seeing an ostensibly happy person who has forsaken the roles and goals designated to them by their body forces Jess and Tom to confront a bevy of doubts about their own life choices. Were their investments in marriage, family, and the other trappings of gender worth it? Be it the opinions of relatives, cultural mores, or messaging through media, Jess has been inundated with the idea that wife-and-motherhood is her only real respectable option, while Tom often feels like his entire worth rides on his ability to be man enough for any given situation (which, more often than not, means pretending he doesn’t have feelings). Now, here’s a person who exists outside of all of that, who, by most metrics, is failing to fulfill any gendered duties but still seems to be, all things considered, fine.

In an effort to win over the room and ingratiate herself to the parents, Miss Maxi Dress introduces herself with a joking apology for all the papier-mâché forest animals and kiln-baked clay mugs that will be cluttering their homes for years to come. The unexpected jest earns laughs (some polite, like Jess’s, others genuine, like Tom’s). It breaks the tension, she delivers her spiel about second grade art class, and she meets parents for individual check-ins.

Jess and Tom learn that Timothy’s doing fine in art class—one should hope; the stakes are pretty low here. She lets them know that he enjoys painting and he does a good job of cleaning up after himself at the end of the period, which is pretty much all that matters at this age. What’s of greater interest to Jess is the easy rapport that this art teacher succeeds in establishing rather immediately. She’s charming without being too needy about it, but it’s still clear that she wants Jess and Tom to like her. It makes her unthreatening. She obliquely but transparently references the fact that they probably care more about reading and math at this point, and they really have nothing to worry about here. She’ll encourage any enthusiasm for the arts that she notices from Timothy, and she’ll make sure he’s not coming home with paint all over his clothes (but, she adds with a wink, they stick to the washable stuff, just in case).

The rest of parent-teacher night went by without incident. Timmy was doing well in math, but seemed a little unmotivated in reading. Jess and Tom were asked to make sure he’s keeping up with his homework, but overall they learned that their son is a bright kid and a pleasure to have in class.

On the drive home, Jess and Tom compared notes from the night over 106.7 Lite FM. Fergie’s “Big Girls Don’t Cry” is about halfway through the bridge when Jess asks, “So what did you think about the art teacher?”

Tom shrugs, “Seemed fine. Kind of a glorified babysitting job, yea?”

“Yea. People were making such a big deal about the whole thing, but she seemed totally fine. I mean, good for her, you know?”

“Yea. Seemed like an art teacher.”

“...need to be with myself and center / Clarity, peace, serenity,” Fergie bemoaned, perfectly.

“She was funny, too!” Jess offered, generously. If she was being honest with herself, this new hire at the school had been a bit of a point of gossip among the moms, and she was eager to get her husband’s take. “And, you know, pretty!”

“Mm,” Tom responded, neutrally. “Seems like a cool person. I’m excited for Tim to give me a mug for Christmas this year.” He said it like he was being sarcastic, but he couldn’t suppress a bashful, childlike smile. That mug would proudly hold the pens at every desk Tom would ever sit at again in his life. He remembered the one he made for his dad as a kid. He didn’t do a great job at sealing it, so the thing couldn’t really be counted on to hold liquid, but pens it could handle. After his parents divorced, Tom’s dad bounced around a few different apartments before finding a place that could work long term, and he made a point of showcasing that splotchy green, glazed mug on his desk in every single one. When Tom saw it, all of those sad, otherwise undecorated one-bedrooms felt at least a little bit like home. At the time, he viewed it as something of a hollow gesture. It didn’t take the place of the actual care and quality time he needed from his dad in the wake of the divorce, but goddammit if that mug wasn’t still sitting on his dad’s desk to this day. He fully intended to cherish Tim’s mug the same way, and earlier that night, he visibly lit up when he learned that this would be the year he could start.

“…It’s time to be a big girl now / And big girls don’t cry…”

Jess had noticed Tom light up at the art teacher’s joke about the mugs. After fourteen years together, she could tell the difference between his cadenced chuckle that acknowledged a funny joke and the breathy scoff-giggle that escaped from the back of his throat in sincere, physical response to delight, surprise, or joy. Now, while Fergie was finishing out her “La-dadadadada”s, Tom had just brought up the mugs again, then fallen quiet with a moony glow. He had also, it was clear to her, deliberately declined to comment on whether or not he thought the art teacher was pretty.

Now, Jess and Tom were a cool couple. They didn’t make it this long without being realistic that they would both find other people attractive. They were married adults, and neither was the jealous type. Since their early twenties, they both prided themselves on their ability to “just be chill.” In fact, it’s one of the things that drew them to each other. Over the course of their entire relationship, there was only one instance of anything approaching infidelity, and that was really just the result of a miscommunication between messy twenty-somethings (basically, Jess had started a separation-anxiety fight right before she left town for a childhood friend’s baby’s christening, leaving Tom with a barbed “I just need some time to think about us,” which he took as “We’re on a break,” and he half-heartedly hooked up with this chick Kerry, who was like his work wife from a previous job, but the whole thing blew over pretty quickly, and if anything, it affirmed how much they meant to each other—they were engaged within the year).

All of this to say, Jess had ample faith in the strength of her marriage, and her mind wasn’t lingering on this art teacher out of some basic insecurity. So, why then? She found herself cross-referencing Miss Maxi Dress with the night’s other players. None of them burrowed into such a cozy spot under Jess’s skin as she had, but perhaps they could offer some illumination by contrast.

Mrs. Moore, a veteran math teacher in slacks and a dowdy blouse, looked like a sweet grandmother because she was one. She was something of a legend at the school, and every parent was grateful that she’d be eking out one more year for their kids before she finally retired. She and Maxi shared in common their warmth and ease, but age was an obvious difference.

Mrs. Kinney, the chipper young ELA teacher, sported some khakis with a white button down under a rust cardigan. She had grown up in the area, but attended the neighboring, not-quite-rival elementary school, which she relied on as a bit too heavily in a way that became annoying. Both arts teachers (language and fine) were sunny, eager to please, and relatively young. Kinney, though, who led hard with the “Mrs,” narrated her own story too rigorously. She came off as deeply invested in being taken seriously as an educator, or maybe just as an adult. The art teacher was easier-going and didn’t demand so much from the parents.

Miss Davis, the administrative assistant, was clearly the faculty’s agreed-upon knockout in a nearly pornographic combination of pencil skirt, backseam nylons, button-up, strawberry-red lip, and updo. She posed silently next to the principal during his address to the parents, and relished all the eyes on her. Those in the know whispered about her thing with the principal, but the real inner circle had moved on to her triangle with the computer science guy and the custodian. When Miss Davis perched by the podium, Jess made eyes with the mom who had looped her in on the scandal, but she truly hadn’t given her another thought until now. The secretary and the art teacher were definitely both hot, but the latter lacked the former’s empowered vampiness.

Could it really just be that she’s trans? That felt so boring to Jess—or maybe it made her feel boring. It had to be more than that. She gnawed softly at the inside of her cheek while she ran the data. The woman in the floral print dress had made bold choices that flirted with the boundaries of “business casual” without violating any of its tenets. In fashion, word, and deed, she was operating according to her own set of rules, but managed not to break any of those silently enforced by her peers. Maybe that was it—above all else, the art teacher was self-possessed. She knew exactly who she was, to a depth that imbued her every move with the sense that she was sharing her most terribly intimate, vulnerable, authentic self.

Just as Jess was arriving at this gem, Tom pulled the car into the driveway. They had been quiet for just shy of ten minutes now, each on their own journey whose first step began in the art class. They paid the babysitter and sent her home before they started getting ready for bed. Tom volunteered to check on Timmy while Jess hopped in the shower.

He peeked through the door to see his son sound asleep. He watched his little shoulders heave softly up and down, in sync with tiny snores. As he lingered, a memory came to him of his father doing this same thing. He was still awake while his dad hovered just outside his bedroom, but he pretended to be out cold. He wondered if Timmy might be pretending, too.

Meanwhile, Jess had just finished her quick rinse and beheld herself in the mirror as she dried off. Like the art teacher, her arms were holding on to this past summer’s final sun kisses. She traced her fingers along her collarbones, then aimlessly around her torso, and tried out a smile. She decided that she loved how it looked. She tried out a few other faces: adoring, excited, powerful, serious, pouty. The last one coaxed out a laugh that landed her back at that smile of hers, and she felt beautiful. She slipped on a satin chemise, hoping that her husband might notice his wife’s beauty.

When Tom came to bed, Jess gave him her smile. When he received it, she fell into his embrace. There, she pressed against him in that old way, seeking. Tom, though, held onto Jess too tightly to allow any undulation to begin. He buried his nose into the hollow between her neck and shoulder and he breathed her. In his arms, now in his lungs, was the woman with whom he had built a life, the mother of his son, his best friend who had given him more than he realized he could hold. He couldn’t possibly pull her close enough, but he would try, and in that, Jess found what she sought.

“Okay, so you’re going to wear this dress and it’s going to put you at the center of a straight couple’s psychosexual melodrama?” confirms Kate.

“Yea,” I say, pleased. Some silence, two small smiles. “Well, I’m gonna brush my teeth and get an iced coffee.”

“Okay. Have a good day, Daphne.”

“Yea, you too. Good talk, Friggle.” I salute her like a sergeant, which she hates, and we hang up. I go through the motions of brushing my teeth and narrowly dodge a meltdown when some errant toothpaste foam barely avoids splashing onto the crotch of this black floral maxi dress. It lands on my feet instead. Fine.

Half past noon, I finally leave the house and walk one block to the coffee shop. The barista tells me I look pretty.