In the year I broke up with someone I had loved and lived with for nearly a decade, I attended four weddings over a period of six weeks. This fluke of timing belied a cosmic indifference that felt so on-the-nose, I couldn’t help but laugh. How funny it was to come out of a nine-year relationship at twenty-eight, I thought, and to start all over at the precise moment when everyone around me was choosing ‘shit’ over ‘get off the pot.’ How hilarious to get sloppily drunk and dance all night in celebration of forever-love when the evidence suggests you’ll die alone. I laughed at all of it, the animatronic caw of a person whose muscle memory has unlearned, over a course of months, passable vocalizations for joy.

I’d spent my twenties watching girlfriends date their way through a succession of assholes, slackers, softboys, and duds, before eventually landing on lovely people who did not meet those descriptors and settling down with them. I’d gone the other way and gotten serious fast with a kind, brainy housemate at the beginning of my second year of university, functionally a hausfrau before I’d even exited my teens. The messy trial-and-error of a dating phase was something I’d escaped, perhaps unfairly, and I wondered at the time whether my lucky roll of the dice had clouded my perception of the actual odds against what I seemed to have won.

My relationship ended for any number of reasons, but a dearth of affection wasn’t one of them. I was unhappy for reasons that felt trivial when I said them out loud, which was almost never; I barely had the language to describe my predicament in the first place. More than anything else, my uncertainty manifested as a physical sensation, a gut-level insistence I no longer had the option to ignore. I was privileged enough to recognize a value in my own happiness and the integrity in making a sacrifice to achieve it. I also knew that to do otherwise would be, at the act’s core, a selfishness of its own.

The truth was that my on-paper reasons were there, and they still make sense after the fact. The timing was bad, for one. My dreams for myself were bigger, louder, more insistent than my dreams for an us – any us, even hypothetical pairings that would never exist. I was ambivalent about marriage, period, and about children even more so. I’d just put in an iud that I vowed not to remove until it expired in my mid-thirties. Above all, there was too much I wanted to do, too many windows that my sanity demanded I keep open. The trappings of permanence made me feel uneasy, and for years youth had let me push them away, until the day it abruptly stopped being enough.

The relationship might not have ended at all if I’d been born even a generation earlier. The kind of life I wanted lacked precedent among the women who had shaped me, by their own choice but also by their more limited options. I didn’t have much money and my professional prospects were limited within a dying industry of ideas and words. Yet I intrinsically grasped that my life could be an adventure of my own making; this seedling of a vision felt too precious to set aside, even as it rendered my heart ugly and wrong. I suspected that nobody in my family understood, nor anyone in his. I steeled myself to be hated.

That summer, during the worst of it, I paced outside a Chicago McDonald’s while waiting for a train to cart me home from a music festival whose details the anguish of that period has all but erased. The July heat was oppressive, just like everything else.

My father was to pick me up from the train station in Milwaukee, my hometown some two hours away, where I was hauling my corpse for an annual summer visit. In the shadow of the McDonald’s sign, I phoned him my whereabouts. On the other end of the line he sounded almost as deflated as I felt. My grandfather was slowing down, he said. His memory wasn’t so good. His heart, even worse. My father’s pained resignation to his own father’s mortality was taking a toll, despite the distributed support of a half-dozen siblings and my mother, his wife of thirty-four years. I thought about how, in thirty-four years, I would be five years older than my father was at that moment. I thought about how, one day, much sooner, he would be old, too.

‘Life is hard,’ he said, pointedly, ‘and harder if you’re alone.’ Don’t make a decision you’ll regret for the rest of your life, he added. Or maybe I’d inferred it.

Life is hard, and all the harder because of decisions like the one I ultimately made: to walk away from a sure thing. Nuts! Pause for a moment to consider the tremendous novelty of that choice within a society whose institutions continue to uphold the nuclear family as its foundation. The primacy of personal growth and self-actualization overrides consideration of the collective yet counterintuitively sets us up to risk thwarting our own self-interest – that is, it sets us up to do what we want in the moment. And so, this terrifying leap I ultimately made was the only thing I could talk about for many months, daring anyone at all to talk some sense into my hungover husk.

Today, we have the liberty to step away from relationships, to start over. It’s a licence many of us may not even think of as a freedom, having gulped our first breaths knowing in our bones that we exist to follow our bliss. Don’t know what your bliss is? Fake it ’til you make it – the late capitalist mantra that’s arguably the central proverb of contemporary wisdom.

It seems almost retrograde to regard individual relationships as critical pivots in the grand scheme of our self propelled stories. It’s unlikely someone will deny us a job on account of a domestic partnership that didn’t work out, much less lock us up, though both have been true within the last century. As of the 1970s, we no longer have to prove mistreatment in order to obtain a divorce, and we don’t even need to marry in the first place. It’s taken for granted that a majority of us will form multiple romantic partnerships over our lifetimes.

And yet, we agonize over our cultivation of meaningful human connection. We make couple selfies our avatars on Facebook and Instagram-post our friend groups with the zeal of paparazzi. Our intimate freedoms are startlingly new, and they absorb us in exhilarating pursuit. But the basic blueprint of Western partnership – a marriage between two people until one or the other is dead – remains tethered to a time that was not so free, nor so distant. Our grandmothers’ mothers were not likely able to own property, to economically support themselves, or to vote. For my contemporaries plumbing the uneasy depths of semiyoung adulthood, the burden of history hangs in balance with the tightly bundled load of our personal needs and desires. The archetype of successful adulthood still rests on finding our ‘other half.’

The person with whom I broke up those years ago was (and is) kind, sweet, smart, and good. The dictionary definition of a mensch, he also made (and, as far as I can guess, continues to make) much more money than I do. I adored his family and knew that, even after the months and years that would inevitably pass, I would continue to miss them; they had become my family, too. It felt cruel that I had been raised with a set of expectations about partnership that would make this terrible outcome also, ironically, the one that was best for everyone.

That gruesome irony is what this book endeavours to unpack. I wanted to get to the bottom of the cultural and economic developments that have enabled women like me to break up with stable and decent partners, or with any partners at all – and why, despite those developments, the decision to stay or go has remained so charged. When did it become so damn difficult to figure out not only what we should want, but what we do want? I wanted to understand where the material concerns and emotional ethics of partnership had historically diverged in the first place – where and how it had become impolite to mention money and love in the same breath, as though their symbiotic relationship isn’t gleefully reinforced by holidays that celebrate consumption or karat counts on rings.

The road to our status quo was paved by history’s haves. Marriage was about the allocation of stuff, and its backstory is a timeline of wealth-preserving demands by white, property-owning members of Western society. In many respects, our love lives continue to be governed on a presumption of heteronormativity, whiteness, and material comforts.

Romantic love in long-term partnership was, itself, invented alongside the market economy. The partner choices we have as women and femmes of any sexual orientation are a direct inheritance of the conditional freedoms we have gained as a by-product of capitalism, made ambiguous by the inequalities that this system continues to reinforce. My generation of women and femmes might be the first with the unlucky privilege to weigh the contradictions of an ideal partnership and choose outside the conventions of shared wisdom. We are, whether we like it or not, pioneers. What do we do with this mantle we’ve inherited?

For those of us who are not straight-leaning, who are not gender-conforming, who have crossed the threshold of middle age in the absence of a partner, this question probably feels a bit dull. The heteronormative rites of middle and upper-class adulthood are small existential potatoes, all in all. But never before in history have we demanded so much of our significant others, such complex criteria along

social, economic, emotional, and sexual lines. To complicate existence even further, the parameters of an ideal life have never been less clear. It’s hard to know what we want when the potential stakes are higher than we might want to admit. And despite the widely accepted notion that personal happiness is paramount above most other things, the liberty to accept this as truth is so new that it isn’t always apparent when we do or don’t have it.

Just as the flaws of past relationships become clear once viewed through the wisdom of hindsight, the developments throughout history that have allowed for men, women, and everyone in between to have some semblance of romantic freedom seem obvious when traced backwards from the now. Nothing is natural. We are a pragmatic species. At the same time, these bread-crumb paths through the forest of our past aren’t necessarily the ones we might have guessed. This book is a forensic investigation of the material conditions that have led us, particularly as women, to the present moment – the political, religious, and economic shifts that have made breaking up possible, yet still so hard to do.