25: The Death of the Single Girl
And the journey of a writer
This fall, I achieved a goal I’ve had for years. I got an article I wrote published—a piece about the app Feeld that ran on Mashable. I grew up worshipping online media—Jezebel shaped who I am as a person and writer—and I’d long dreamed of contributing my own essays to websites. After years of toiling a way, it finally happened.
But I found myself almost immediately moving past the win. I tend to undervalue my successes. I move past good things because to celebrate them seems to suggest that I may never climb higher than that again. I want this article to be the first of many, so within hours of publishing it, I’d moved on, already focusing on my new goals, berating myself for new essays and scripts that I didn’t think were good enough.
Now it’s two weeks until the end of the year. Even though my inclination is to look back at 2024 at the ways I’ve fallen short, I want to celebrate my accomplishments, to not be afraid that to appreciate them is to mean that they’re the best I’ll ever achieve. And maybe to do that, I need to look further back, beyond just this year.
Below, I’m publishing an essay I wrote at 25. At that age I was uncertain about both my writing skills and my new role as a girlfriend. I write about my trepidation with this new title. I had just started dating Ross, my first boyfriend. And although he was everything I’d ever wanted, I struggled with the sudden shift in identity. I was in a partnership, I was a girlfriend, and it felt new and uncertain. I’ve been with Ross for so long now that I’ve lost that sensation, and finding this essay was like dipping back into that age again, that summer where I felt so excited and fearful.
And this piece serves as a time capsule both in terms of its content and where I was in my writing journey. I’d pitched it to several places after I wrote it, and I only heard back from one. Haley Nahman of Man Repeller told me that the essay wasn’t a right fit for her, but she believed it could be published elsewhere. That was enough of a push forward for me to keep writing, even though this piece didn’t end up published. And rereading it now, although I see phrases I’d sharpen or ideas I’d rearrange, I can recognize my skill.
Maybe the key to appreciating my success is acknowleding the steps I took to get here. Not just that I wrote an essay at 25, but the decision to stick with writing. With deciding to start a Substack in 2020 because I was unemployed and bored and sick of my writing only being for me. For taking the essays on my Substack more seriously, for putting in hours of time tweaking and editing not because I’d get paid or it would be widely seen, but because I’d get better. For facing my fears of rejection and asking for help, for naming this dream out loud, for talking with my friend who is an editor, for tweaking my pitches and working outside my comfort zone to get my work published.
So I present this essay, as a moment in time and a step in my journey. A reminder of how I felt early in a relationship, as a signifier of the writing I’d had yet to do and the work I’d already done. Of an uncertainty to claim the signifier of girlfriend, and in this meta narrative, as writer. And my journey to choose to embrace those titles.
September, 2019
I made being single my identity. Then I found myself with a boyfriend.
…
When I was 22, I moved back home to NYC after college with one purpose: to meet and fuck as many guys as I could get my hands on. I was coming off of four years at a small liberal arts college where I had razed through all of my potential hookup partners by the time I reached my senior year. To be a single woman in New York City was a rite of passage, as immortalized by Sex and the City, and armed with with Tinder, Bumble, Hinge, and The League, I was ready for this to be my time.
I took to the Single Girl lifestyle with a vengeance, going on at least a date a week. I’d meet them at bars, or go on walks in the park, or meet for lunch during my internship. I’d have phone sex with guys I’d never met, or invite tinder prospects to my house for wine. And whenever it was over, I’d text my friends, rehashing the awkward, titillating, exciting, weird moments in detail. I quickly became a dating expert among my friends, editing their profiles, looking over texts guys had sent them. I was so riveted by modern dating I created a podcast titled Millennials in Heat dedicated to it. At parties, I doled out my dating stories, gleefully reciting the time I had sexted with a former child actor, watching peoples’ eyes widen when I shocked them with the time I got seduced by a high-end male escort. It was my drug. It was my identity.
And two years into mastering this, I met my boyfriend.
I met someone who I liked and who liked me, who made me feel good and safe, and I wanted to be with him. It was great in the beginning. I rarely thought about my former life. It wasn’t until a few months in, when I got a late night DM from a guy I used to sext with that I started to feel rumbles, remembering the thrill when he would ask me if I was getting fucked recently. I kept noticing my former self creeping in: when I saw a cute waiter at Jon & Vinny’s, I would catch myself fantasizing about him grabbing me on the way to the bathroom and us passionately making out. When I see acquaintances at parties who ask me for my latest escapades, I just shrug and mention having a boyfriend. No late night rendezvous. No hand jobs with a 20 year old in a dirty toyota on a random street in Silverlake.
When I feel the remnants of my single life slip in, I think about Courtney. See, Courtney is the girl who’s only known relationships. She met her boyfriend in high school—the story of how she lost her virginity definitely has rose petals or prom involved—and stayed strong while doing long distance at college. Now they share a lofted apartment their parents bought them in downtown Brooklyn, and have an Instagram account for their dog Peggy. Courtney has never known the draw of singledom, no late night DMs from the 40 year old executive. She has only known commitment, comfort, and couples Instagram posts. I picture her, petting Peggy, laying next to her boyfriend, ruffling his hair, to push away the thoughts of a waiter. I envy her ignorance. I wish I didn’t know the draws of singledom, the excitement, unpredictability, and the weirdly addictive suffering.
Noticeably absent in what I miss is the men. Because, I don’t miss them, or the actual sex, or the painfully awkward dates. I have no desire to sleep with other people besides my boyfriend. And, evidence via my saved snapchats showing a picture of me drunk with the caption “haha deleted tinder I hate all men xoxo sarag freedman”, prove that I didn’t enjoy being single the whole time. So ...what do I miss about being the Single Girl?
Here’s the truth about the Single Girl. She isn’t actually the girl going on the dates. She’s not the one having mediocre sex with a stranger, because to leave a date without something happening is to admit a total waste of time, which is, to be a failure. She’s the girl in the stories that I tell at parties, that I would recite on my podcast. She is the girl I like to reduce myself to because she is fun and exciting and to accept myself at my fullest, most complex feels depressing and unrealistic at the same time. It’s much easier to reduce myself to the girl that’s always single, who’s always going on dates, who has fun tidbits. A guy could treat me like shit, but I was the one with the story. I had control over how people perceive me.
And without this new wall of an identity, I didn’t.
…
Over the phone the other night, I told my boyfriend about the essay I’ve been writing.
“Do you miss being single?”
I took a long pause. On one hand, I didn’t want him to feel like I didn’t absolutely love being with him. On the other, I didn’t want to lie.
“Yes,” I admitted, “Sometimes.” I paused. “But that doesn’t mean I don’t absolutely love being with you. I love being your girlfriend.”
“I know that,” he answered, confidently, “but you were single for a long time. It’s still a part of who you are, in some way.”
And maybe this is really the death of me, the Single Girl. It doesn't end with being in a relationship. It ends with someone who’s willing to accept all sides of me, who wants to see the complex person I am. I miss being a version that was easily presentable, easily understood, and always entertaining. And now? I can’t rely on click-baity stories. It’s time to embrace my whole, complex being. Single Girl included.
Thank you for reading! If you feel moved to do so, would love if you shared or subscribed <3
Love this!!