Today I’m Going to Share a Sad Story

Twenty-one years ago today, I lost my virginity.

That experience itself is not a sad one, but it’s important; I was 14-years-old, and having already had my first sexual awakening a few months before, I’d known when I started dating Toby that he would be the one. He was three years older, an incredibly tall and thin brunet with long hair, graceful fingers, and the most prominent, lovely nose. We’d started phoning one another after he stopped me on the sidewalk outside my Taekwondo studio, where he’d told me he loved my smile and eyes.

What he didn’t know then was that I already had a crush on him. We’d both auditioned for Tevye and His Daughters a couple months before, and while I’d had to drop out of my miniscule role because I had too much homework that I took very seriously, he’d gone on to perform as Tevye in a manner that didn’t fit his 17-year-old frame. It was on that stage Toby struck me as different from all the other boys, as if hosting wisdom beyond his years, but also a presence that couldn’t be explained in any terms I understood then. It wasn’t that he was confident, or dominant, or anything we might imagine when we think of onstage presence; instead it was an aura of listlessness, of discomfort. He was a young man who struck like the gentle beat of the carotid through translucent skin—rich with life blood, and yet so faint you might miss the ghostly tick of who he was.

I discovered I was right about this feeling when Toby and I started dating. There was something about the way he gazed wistfully out the window, and the unusual things he chose to discuss and dwell on. Then there was poetry; long before we’d ever kissed, I’d read him one of my early poems when we sat together in the park. I’d stopped mid-line, suddenly embarrassed and thinking there was no way anyone would really want to hear this blubber I was writing in which I poured out my soul, my ache, and all my love—but Toby did. After, he begged me to write more, to read to him over the phone so he could savor the words and ask me all about what I was thinking when I wrote them. Occasionally—after much encouragement from me—he shared one of his own, and in time, this became our habit. Poems and letters formed our connection, the secret we’d found to express ourselves beyond the physical moments we spent cuddled in the dark, talking of dreams and the futures we imagined for ourselves. Mine were tangible and real, fantasies I could make happen if I set my mind to them. But in Toby’s written words I learned something with which I’d never been familiar: the idea that someone could truly find himself not fitting in this world, that his very existence, for him, was in question at every moment of every day.

By the time we decided to have sex, Toby had shown me more of him. There was a youthful playfulness that distorted his face when he tried to fit in, as if underneath something lingered, a quiet unease that only spilled out on paper when he spoke serious fantasies of living in different eras and places. He made it sound romantic, this obsession with running away from here and now—and this was part of the reason I asked him to be my first. It happened in the middle of the night after he snuck his long, lanky body through my window, kissed me while he slowly peeled off my clothes, and then laid me down on the carpet of my bedroom floor as the moonlight streamed in through the open window and over our skin. Toby kept his lips on mine the entire time, as we both tried, desperately, to stay silent lest we get caught.

In truth, the experience was not what I’d expected. I wondered why people made such a big deal out of this thing. All the other physical acts we’d shared had struck me as more pleasurable, more intimate—and what I wanted in that moment was something more meaningful, to light a candle by which we could whisper our poetry aloud, like we did all the other times we’d been together. I’d been trying to make sense of Toby for so long, and now, this close, this forcibly connected, I needed to understand him, to peer into his soul and see why—despite all his love, his caresses, and the way he claimed he felt happier with me—he still struck me as so lost inside his head.

Part of a poem once written for Toby

Toby’s Poem

Our lovemaking continued for only a month after that, each time better and attempting to draw us closer. It was a physical act to meet my ache for understanding, and perhaps one that represented his need for a world he couldn’t find in his family, friends, or the comings and goings of high school life. And when we broke up, it wasn’t because he was acting as the lost young man I’d come to know and treasure, but instead the laughing, joking boy he thought he was supposed to be.


It was almost four years later we ran into one another, and everything, while different, had stayed the same. Toby complimented my eyes; I told him I still loved his nose. He was thinner, lankier, and his eyes had grown darker somehow, like he’d taken on more of the world’s weight and it had sunk the skin around them as a mark of all he had to carry. But when he asked if I still wrote poetry and I flashed a reminiscent grin, he brightened up. He told me he missed my smile and that we should catch up over poetry and wine.

I honestly can’t remember much of the dinner we shared when we met a week later. The trials that had happened in our lives—rumors that had spread around town about me, and the rumblings I’d heard about him through friends of friends—were all irrelevant as we sat across from each other. We both pulled out the notebooks we’d written in over the years, eager to share everything we’d thought and felt about life, other lovers, and what the future would bring. After our meal, Toby bought a bottle of red while I stood outside the liquor store in the cold night air, wondering if the love we’d make would feel the same to an experienced 18-year-old as it did to the virgin he’d soothed and welcomed into his mystery all those years before.

When we arrived at my house, we uncorked the wine and sat facing each other, poetry in hand as we read, back and forth, for the next couple hours. There were many toasts, many utterances of encouragement, many awed shakes of heads at what each of us had expressed over these few years that felt like a lifetime of change. He stopped me, at one point, telling me he was so glad I’d never stopped writing. I’d dropped my notebook to my lap, beaming and blushing—no one but Toby had read so many of my words, and certainly no one but him had encouraged me to keep writing them. In the same way, I loved what he’d done with his own, and I told him so.

It was somewhere after our second glass we started to kiss.

The memory is ancient and tainted with the fuzzy haze of wine, but what I do recall is this: two naked bodies curling under the sheets, fingertips grazing each other’s sides, tracing memories and yet learning something new, something changed. There was more wine, then more poetry. We whispered it as we made love again, this time a little older, more sure, knowing it was the magic of the lines we read that fueled our fire, that maybe seemed to others strange—two people reading as they arched and bowed, breaths wavering between the words—but that for us remained the secret to our true selves, and what we sought to understand in one another. Our rapture was in poetry, and when we woke in the morning and he kissed me goodbye, I remember thinking it was the real way we were supposed to end: the writers who’d loved, not just the lovers who’d written.

I lost Toby after that night. I heard he moved away, somewhere strange, some other country he’d always wanted to visit. As close as we’d been that night, I’d read in him that comfort in his skin remained a diaphanous, tenuous thing—that despite his beautiful words and loving touch, he still wasn’t all that sure of the world or his place in it.

Wherever he was, I hoped he’d soon find the solace he’d been looking for.


It was over four years later I got the news.

My life was a vastly different one then. I was nearing the end of a five-year relationship that lasted five years too long, one that, without saying too much, broke me in ways women should never be broken. And it was while this boyfriend visited my apartment that my best friend called to tell me what she’d heard about Toby through some mutual friends. She’d dated him too, for a short while before I’d ever met her—but through the years, she knew who and what he was to me.

She spilled it all in a moment, her low tone signaling the gravity of what she had to say: Toby had been living in Europe with a pregnant girlfriend. No one had seen him in a while, but everyone thought he might finally be happy.

And then he killed himself.

My reaction had been stifled by the look I got from my boyfriend. I didn’t know how to act, how to feel. I’d never lost anyone before, but I found myself remembering Toby in that instant as I’d first known him—a lost young man, living in the wrong world, the wrong time, searching for something that fit and never quite finding it, writing letters and poetry that forever tried to make sense of it all.

“So he killed himself and he was your first. Big fucking deal,” was what my boyfriend said to me. “You dated that guy? He was your first? What a loser.”

And because my reaction would determine what came next between us, I didn’t say anything more.


They say you always remember your first, and I believe, for many, this is true. There is something to be learned in your first time—awakening, desire, love, pain, change. And yet, when I think back to my “first,” I hardly remember that moment with Toby on my bedroom floor. What I remember instead are those moments sharing ourselves in the poetic way only we understood, and, deeper than that, the lost man I tried so hard to understand but never fully could. With it all usually comes a sense of grief and loss, a feeling that rose and fell so fast then, never expressed in a way that suited the connection we shared every time we read our words.

Most of all, there comes the acceptance that sometimes, you can never truly understand what’s going on inside a person’s soul. You can encourage them, and you can empathize, but there’s always so much more beyond what they will let you see.

And the only thing you can do is treasure them anyway.


For Toby.

Posted in About, Confessions, Musings, Poetry and tagged , , , , , , , , .


  1. I feel for you, I really do. My first will always have a special place in my heart. We were young too and we split straight away but if I heard that something so tragic had happened to him I would feel terrible, luckily I’m in a supportive relationship so my reaction wouldn’t matter. But you are so right, treasure those around you.

  2. Jade,

    As someone who has experienced similar losses, I know the kind of impact they can have, even when they are folks who you cared about long ago. It’s so hard to get shut down in your immediate response, makes it harder to mourn. I’m so sorry that your boyfriend said those things to you. That was not ok. I’m glad you feel able to write about Toby now, and that I got to read it. A brave and vulnerable post. Thank you.

    • Dear Xan – thank you so much for all you’ve said here. It means so, so much. I agree that the shutting down is a difficult piece when it comes to the mourning process, and I really appreciate your thoughts. I admit I was nervous at first to write this, but in the end it had to be shared. Toby was a lovely soul, and I only wish we’d gotten to know him longer. XX

  3. Thank you for sharing such a poignant a part of your personal story. You write in a very relatable, heart-rending way.

  4. Oh, I’m so glad you just tweeted this again to remind me of it…I read this back when you wrote it but it was before I set up Exposing 40 and so only had professional blogging profile and couldn’t comment on any of the non work blogs I had bookmarked! I thought this was the most beautiful and poignant piece and I loved reading it then, and again now. Xx

Leave a Reply

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