But Actually, What Does ‘Single’ Really Mean?

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Photo: J.V. Aranda

Welcome to It’s Complicated, stories on the sometimes frustrating, sometimes confusing, always engrossing subject of modern relationships. (Want to share yours? Email pitches to itscomplicated@nymag.com.)

I’ve learned over time that there are certain inevitable moments on dates, things I’ve come to always expect. There’s that moment after you finish your first round of drinks where you both wait for the other to suggest a second, because neither of you want to seem too eager. If you clear that hurdle, one of you will accidentally suggest something the two of you should do together in the future, and then have an internal meltdown while waiting to see how the other will respond. And just when you feel like you’ve somehow circumvented all of the awkward first date conversations, the sadist sitting across from you will ask the most stress-inducing question on the planet.

“How long have you been single for?”

I’ve always been self-conscious about my answer. By my count, I’ve been single for just about four years. I split with my last man boyfriend in April 2014, after nine months of arguing about money while he pressured me to move out of New York and back to New Jersey. It seems like a while to be sans-relationship — so long, in fact, that he had enough time to move on and get engaged. I never mentioned that part, but still, I couldn’t shake the feeling that there was some stigma involved in staying single as long as I had when it wasn’t a lifestyle choice.

But while a few months back, while on a date at Barcade with a handsome Brit, I was confronted with another wrinkle to that question. We were going head-to-head in Street Fighter when he asked me. When I told him, he glanced at me just long enough for me to sneak in a roundhouse kick. “You really haven’t been on a date in four years?”

I clarified that my most recent serious boyfriend and I broke up four years ago, but that I’d been on plenty of dates since then. “And I dated a few of those guys for a few months at a time,” I clarified.

“So you haven’t actually been single for four years,” he retorted, and then delivered a devastating KO to my digital doppelganger.

I felt like I’d been knocked out, too. I’d thought of myself as a single woman for so long — I’d been ambivalent about it at times, sure, but it was part of who I was, how I’d spent a significant stretch of my 20s. I’d even made a career out of it, writing about the ups and downs of dating in New York as a single millennial for the better part of two years. And now here was this handsome man with a delicious accent telling me that I was wrong.

“But those guys weren’t my boyfriends,” I pushed back. “We weren’t in relationships.” My date countered by saying that I’d had some kind of relationship with them, though. Didn’t those count for something?

He was right. In the four years since my ex and I had broken up, I’d had a handful of month-long dalliances with a handful of men. One was an older creative director who I’d see for a few weeks at a time before parting ways, only to start up again a few weeks later. Another was a trainer who would stay at my apartment two nights a week, and I’d cook him chicken dinners in my cast-iron skillet and keep his favorite wine in my fridge. That went on for two months. And another still was a man I met at a bar who I saw off and on for two years who then wound up living with me for a full month one summer. None of these men were secret, and when I was with them, I wasn’t seeing anyone else.

But none of these men were ever my boyfriend. And because of that, I’d written them off.

After my date, I started having conversations with other women about how they defined being single and the results were mixed. Most could easily state the obvious — someone who wasn’t in a relationship. But when I asked friends to define what a relationship was, things got hairy. “If you’re boyfriend and girlfriend,” was a common answer. But what if you were exclusive, but didn’t label it? What if you were committed to each other, but also allowed to see other people? When I started presenting these questions, answers became less sure.

I started to realize that my handsome Brit was right. Given how much dating has changed, and how complex our relationships have become, there isn’t really a hard-and-fast definition for what “single” is anymore. In my four-year period of self-declared singledom, I’ve met people and gone on dates and had connections that were important to me, even if they weren’t defined. As soon as I recognized this, “single” morphed before my eyes from a fixed category into more of a temporary state of being that I could define completely on my own. My dating life didn’t need to be a binary thing, in which I was either single or someone’s girlfriend; there was room to ascribe meaning to those dalliances and flings in the gray area, too.

Lately, I’ve been associating myself less and less with the word. I’m not seeing anyone currently, but it feels good to put some distance between myself and a label that I felt so self-conscious about. Instead, I consider myself between relationships, happily exploring what the world offers up, and open to everything it sends my way.

But Actually, What Does ‘Single’ Really Mean?