Katy Waldman tells of her romantic experience with an unskilled sexter.

My Awkward Nights With a Bad Sexter

My Awkward Nights With a Bad Sexter

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Jan. 21 2016 11:59 AM

Talk Dirty to Me, Badly

He texted constantly, but he was lousy at it. A memoir of romantic ambivalence and self-abnegation.


Animation by Lisa Larson-Walker. Photo by michal-rojek/Thinkstock.

I met Miles online. Obviously his real name isn’t Miles. We had things in common: We’d both lied about our heights on our OkCupid profiles, and we hadn’t seen Breaking Bad. He was a texter. He texted constantly, but the spigot really opened around 11 p.m. Where are you, what are you wearing, did you miss me today, where should I kiss you? We’d been on several dates so far; we’d held hands and exchanged a chaste peck on the lips. Our digital relationship was hurtling forward at warp speed despite the leisurely in-person getting-to-know-you process.

Katy Waldman Katy Waldman

Katy Waldman is a Slate staff writer.

I had never really sexted before, and I was terrible at it. “Tell me your fantasy,” he’d say. “Be specific.” And I would feel lost, nervous, not to mention his wording reminded me of a college essay prompt. “I want to be touched,” I texted back, lamely. And then, because I thought it sounded erotic, I added: “On my body.” 

He was confused. “Like a full-body massage?” 

“Mmm,” I replied. It seemed like a sultry, enigmatic syllable.

“Just say exactly what you want me to do,” he wrote.

This was typical Miles—forcing me to do all the work. When I asked him about his fantasies, he demurred and pressed me to elaborate on my fake ones. I thought that maybe this was how adult relationships functioned. Thank God Miles was there to show me the ropes!

Plus when I saw him in person we had nice, banter-y conversations and told each other cute stories about our days. Sometimes I’d mention something I’d read and his face would go blandly attentive. “Oh, cool, cool,” he’d murmur and then change the subject. “Miles is a space cadet,” my friend told me. I thought perhaps I was boring him. He’d just moved to D.C. and was teaching tennis at a fancy country club. I imagined him instructing all the preppy, long-limbed teens and crusty bankers from my suburban childhood; when I pushed him to describe his clients, though, he talked about their tennis strokes: She doesn’t get under the ball, his forehand needs work.

Was it strange that he rarely wanted to hug goodbye? That he didn’t seem to understand when I was joking? The incessant e-flirting reassured me: If Miles weren’t into our “relationship,” I told myself, he certainly wouldn’t bother tapping out requests for “the dirtiest thought I’d had all day at the office.” (Which became another source of anxiety: Did most people entertain scandalous daydreams at work? I lied that I wanted him to undress me in a conference room.)

One night, Miles texted me: “I get so turned on when girls wear dark stockings.” I was lying in bed willing my phone not to buzz so that I could go to sleep, but when I saw the message, I threw off the covers and ran to my dresser. Long ignored, the diaphanous black tights rustled when I shook them out. I stretched them so I could see the delicate mesh of the threads, watch the opaque webbing go translucent. A boundary that wasn’t. From then on I wore stockings on all my dates with Miles.

* * *

The next evening, on the way back from dinner with a high school friend, my phone bleeped. “I think it’s hot when girls put on black nail polish,” Miles said.

“Reeeeally,” I typed back, confused by my sudden irritation and wondering if the CVS was still open. Surely they had black nail polish.

“Want to watch a movie at your apartment tomorrow?” he replied. “You pick the movie. Something good! You’re so sexy. Text me when you get home.”

* * *

He arrived the next night with wine and a little pumpkin and a bag of Skittles. After he complimented my nails—which I’d Sharpied black using a co-worker’s marker—we sat on the couch drinking the wine, eating the Skittles, and watching a low-budget horror film in which a farmer and his family were possessed by ghosts. Miles pulled me closer at the right times and made the correct ratio of sarcastic remarks to comforting noises. When he paused the movie and walked calmly into the bedroom, I followed him.

I was aware, with every layer of clothing we peeled off, of an answering layer sliding down like a glass pane, a curtain of denial somewhere between my mind and my body. That small rejection of Miles was the price I paid not to reject him completely—or, at least, not to reject him in a way he’d notice. I liked him, or liked going on dates with him, or maybe just liked going on dates. A few hours later, once he’d left and I was rinsing the wineglasses in the sink, I heard my phone purr. I set down the glass and trotted into the common room, where the ghost movie was still paused on my laptop, the female lead’s face frozen in an expression of horror.

“Hey,” Miles had written. “Tonight was fun. Let’s hang out again soon. Also, for next time: I think it’s super hot when girls are completely smooth ... everywhere. Sweet dreams.”

In the morning I stood in the shower with a fresh razor and methodically removed from my body every last hair I could find.

* * *

My brief, ridiculous relationship with Miles had no bearing on—not even any real contact with—the rest of my life. At a certain point he didn’t return my last text, and I didn’t care, and it was over.

But I did write the story down, out of some sense that there was a moral in it—about self-respect, and authenticity, and how refusing to articulate your desires to yourself can amount to withholding yourself from someone else. Those takeaways, though important, seem boring now.

What I remember most from that time is a fantasy I had. It’s not getting undressed in a conference room. I’m at a bar or show with someone. We’ve been there for a while. The stars are fading. The faces around me are made of something swirling, spot-lit, and porous, except for maybe his, which is dark. I could make a deal—either the obvious kind or a kind that’s harder to explain, a loosening of the weave of myself. Isn’t that the appeal, anyway, of not honoring your own wishes—the chance to become a person magically other than who you are?