A couple of years ago I went out for a drink with a fellow I had briefly dated. Our dating was the kind that happens when you meet someone on vacation (in this case our best friends’ wedding), and keep in touch after you’ve returned to your respective cities. Emailing, talking on the phone, exchanging a handful of visits—interested—but stunted by distance. After six months our chemistry fizzled and we decided to just be friends. It was an affable, drama-free cool down. Not long after, I ended up moving to Portland, where he lived, for reasons of my own (graduate school). We met up once for happy hour and talked about hanging out again, but the ball dropped, and several months passed without any contact.

After hibernating through winter, keeping to myself and my course work, come spring, I was eager to be social again. I spent more time with my housemates; I initiated happy hours with classmates; I went to parties and book readings downtown. I dated a little too, spending a few weeks with one guy before realizing we had different priorities—he, a relationship, and me, not. In the city where I had once felt like a stranger to everyone, a sense of belonging was emerging. Roots were taking hold.

It was in this spirit, that I decided to reach out to the fellow I’d once dated. After all, our best friends were married to each other, and so I wanted to keep things between us good. I was eager to hear his speculations on Game of Thrones, exchange a few restaurant recommendations, and solidify a platonic friendship. We met up for cocktails and he told me about his girlfriend, whom he’d recently moved in with, and the work they were doing on their new house. I was happy to hear this, happy to see him so clearly happy. He asked if I was seeing anyone and I briefly mentioned the last guy I’d dated, but explained that I wasn’t. “School is my significant other,” I quipped, a line I used often.

Then he said something that caught me off guard: “Don’t worry, it will happen to you. You’ll find it when you least expect it.” Those may not have been his exact words, but that was the sentiment. Now, there’s nothing unusual or necessarily offensive about this comment. It’s a familiar aphorism—that you need to stop looking for love in order to find it. But that’s assuming you are looking for love in the first place, that’s assuming romantic love is what we all want to be happy.

It was the “don’t worry” that rubbed me the wrong way. I wasn’t worried about being single. Did he think I was worried? Did I seem worried? Suddenly, I felt self-conscious and confused and…defensive. I’m really happy single, I wanted to insist. I don’t need a relationship. And yet, it seemed that to say such things would be evidence of the very dissatisfaction I was denying. But I was happy. Wasn’t I? Suddenly, I wasn’t sure. I started to doubt myself. If I was feeling defensive, maybe I wasn’t really happy.

As I rode my bike home that night, my mind was spinning, unravelling with these thoughts. He had not said anything explicitly judgemental. Perhaps I was projecting the condescension I detected. But I had that bad taste in my mouth that a single person gets when surrounded by couples who are smugly nesting into banal domesticity. I was frustrated that I could not shake this compulsion to validate my marital status. What was my deal? Was I honestly content, or bullshitting myself? Or is there still a problem with how we talk about being single?

That spring catapulted into summer and one of the first books on my non-school reading list was Spinster by Kate Bolick. It’s a memoir about her relationship to singleness and an attempt to reclaim, or respin, the term “spinster” from a derogatory put down for unlucky and unwillingly lonely women, to a legitimate, empowering choice. In addition to reflecting on her past relationships with men and the time in between them (of which there is very little), she draws on the lives of five “awakeners,” literary women who have flouted or challenged conventional expectations, in and out of partnerships. It was validating. It was fun. Bolick struck me as very New York, very Carrie Bradshaw, and I am not, but I appreciated her perspective.

That said, some were less amused. I was especially struck by cultural critic Laura Kipnis’ response: “What is this need for authors—by which I mean female authors—to defend the domestic arrangements they happen to have chosen? Why don’t men feel the same need to elaborately justify their romantic lifestyles?” She goes on: “Where I disagree is that making one’s own life choices requires so much self-justification, or that anyone needs to have—as Bolick previously felt— ‘a very good explanation’ for not marrying….It’s depressing that women seem to keep forgetting that basically we can do whatever we want. And thus the master’s house keeps getting dismantled, then reconstructed, then dismantled all over again, one dreary brick at a time.”

Kipnis questioned the nature of the conversation itself, suggesting, essentially: shouldn’t we be over this already? As much as I enjoyed Bolick’s celebration of singledom, I enjoyed it because it gave me a validation I was clearly hungry for; Kipnis was interrogating that hunger. I wondered if Bolick and I were stuck in the same defensive rut. What Kipnis said rang true for me; I’ve never really felt like I couldn’t live the way I wanted. I’ve been deterred and discouraged from various pursuits (traveling alone comes to mind), but no one’s actually stopped me. Two generations ago my grandmother was not allowed to go to college because her father decreed it inappropriate for women; I just completed my second graduate degree. I genuinely feel like my life is mine to create, and that usually the only person standing in my way is me.

That said, there are still cultural and social forces nudging women toward marriage and I’m not immune to them. I am not the only thirty-something who senses her parents’ hope that she will “settle down” already, even if my parents have the decency not to say it directly. And I’m sure these pressures range dramatically depending on where you live; I just happen to be lucky to get off easy. So overall, I’ve found the issue of marriage a broader question that everyone faces: to couple or not to couple?

Marriage is still the status quo. It’s an institution, incentivized by the government, that rewards committing your life to another person. To me, the decision to create a life for yourself alone or tie it to someone else is daunting. The stakes feel high. That said, to a certain extent, it’s a false choice. You can, of course, create a life for yourself and have a partner; they needn’t be mutually exclusive. But any relationship will require some kind of compromise, and the degrees to which we are willing to do that are worth questioning. In my own self-doubt following the chat with that fellow, I began to reflect on and evaluate the pleasure I take in being single. I do genuinely cherish the freedoms this lifestyle affords. I love that I make every day as I want. I do not have to schedule myself around a partner, accommodate their needs, or “check in.” My headspace is mine, free from those particular distractions. I savor sleeping alone, stretching out like a starfish, limbs reaching in every direction.

And yet, when the warm weather finally found Portland that year, I started craving connection. At social gatherings, my attention wandered, scanning the room. In the absence of real-life prospects, I started pining after fictional characters. As part of my post-school decompression I binge-watched the quirky sitcom New Girl, unable to stop Netflix from sliding into the next episode. I became fixated on one of Jess’s boyfriends: an adorable British man who shared Jess’s penchant for crafting and randomly bursting into song. I envied their “perfectness” together. Maybe I need to move to England, I’d think, almost seriously. I was distraught when they broke up. I missed him. It was ridiculous.

What was going on? All winter I hadn’t really thought about dating; now the question hovered constantly in the back of my mind. I worried I was regressing, that this was a sign of weakness, that desiring the company of a man was a kind of blasphemy, a chink in my feminism. I tried to ignore these feelings. Invalidate them. I told myself to resist them because giving in meant compromising my independence and that, of course, was my most prized possession. I wasn’t anti-partnership, but I viewed relationships as the frosting on what should already be a delicious and complete cake. A complimentary side dish, not life’s main course. And to be honest, even though I was starting to pine for companionship, I was also genuinely torn about it. Connection sounded exciting. Commitment sounded terrifying. I didn’t want to stop being a starfish. I didn’t want to spend less time doing the things I love at my whim. I also didn’t feel like making much of an effort, which was the only thing keeping me (mostly) off Tinder.

Then one night my housemates and I watched the movie Seeking a Friend for the End of the World with Steve Carell and Keira Knightley. The premise is intriguing: in three weeks an asteroid is going to destroy the world, and human societies are responding in all the ways one might expect: partying, praying, violence—the whole spectrum. When the earth’s death sentence is announced, Carell’s wife immediately leaves him (she literally jumps out of the car and runs away) and he is left alone, devastated. While friends encourage him to find someone to spend his last days with, Carell resists. He doesn’t want some frivolous, meaningless relationship with just another warm-blooded body. Enter Knightley and true to romcom form, you can guess what happens.

After the movie, my housemates and I reflected on how we’d spend our last days on Earth if we knew everything was about to end. And, of course, the point is, are you living that way now? Should you be? In this thought experiment, I was happy to discover that if the world was about to end, I don’t think I would change much. I would probably continue to do most of the things I do now (with more champagne and peanut butter). The only thing that stumped me was the issue of a partner.

Because if I’m honest, before I die, I would like to fall madly in love. I am already fortunate to have loved and been loved in my life. I’ve had a handful of “serious relationships” with some great (and some not so-great) men. But sometimes I wonder if I’ve ever really been in love. Sometimes I don’t know what that means or looks like or feels like. I have friends who can say unequivocally that they are (or have been) in love, and before I go, I’d like to know with certainty that I’ve had that experience. The trouble is, we rarely know exactly how much time we have left. I could have decades; I could have days. So should I prioritize “finding” that now? Or is it really just like that fellow said, and some things you can’t look for?


My sister Amy is nine years older than me, and in my eyes has always been the absolute pinnacle of the Strong Independent Woman. When I was trying to sort out my adolescent self, she was a college student that listened to Ani DiFranco, drove a beat-up stick shift Honda, didn’t shave her legs or eat animals, and traveled to remote parts of the world alone. Her political activism occasionally got her arrested. She had her own sense of style that included bulky boots, big jewelry, and a fearless attitude. As we got older, Amy bounced from job to job, usually non-profit work that paid in meaningfulness, but not in much money. She had several relationships, too, but they weren’t her priority and this only esteemed her further in my opinion. What’s more, I never really feared getting older because Amy was always a decade ahead, embracing age with grit and grace and all-around badassery.

During the time I was romantically corresponding with the fellow from Portland, I was thirty-one and living with Amy in Colorado, in the midst of my own transition between life phases. That fall she turned 40. But Amy wasn’t feeling like a badass. She had been in and out of an abusive relationship, she was overworked and underpaid, and most of her friends were settled with mortgages and children and retirement savings. She told me over happy hour one evening that she regretted not making relationships more of a priority when she was younger. Now she was discouraged by online dating and trying to come to terms with the fact that her biological window for having kids was closing.

I had never seen Amy this vulnerable before and at first I was, honestly, taken aback. This wasn’t how the narrative was supposed to go. I didn’t know how to reconcile my champion of female independence with the very real doubt, perhaps even depression, she was experiencing. I’d always thought that if Amy could live happily on her own terms, then I could too. Full steam ahead. But what happens when you’re suddenly at odds with those terms? When not only do they no longer work, but you wish they hadn’t been your modus operandi? I tried to just be there for Amy. To listen. To hear her thoughts and feelings as her thoughts and feelings, her situation as entirely separate from my own. (After all, I didn’t even want kids, so at least I didn’t have to worry about that, I told myself.) But I couldn’t ignore the underlying feeling that she was telling me something: don’t make the mistake I’ve made. And that scared me.

So perhaps it’s this not knowing about time that ignites what seems to be a defensiveness about being single. I am happy on my own, but when I’m reminded that my time could be running out and that I may never fall in love, I get nervous. I get nervous because there is something wrong both with how we ourselves view being single, and the cultural conversation. On the one hand, we still think of romantic love as necessary for a complete life. If I die tomorrow, I may never have known the intensity of a very specific kind of love, but I have experienced a remarkable abundance of familial love and friend love and other kinds of love. Not tasting this one sliver of the love pie doesn’t equate an unfulfilled life, just as not getting to see the northern lights or the Egyptian pyramids wouldn’t equate an unadventurous life. I’ve had other adventures.

And yet.

I don’t want to be ashamed of my desire to fall in love. Because while I’m grateful to feminism for challenging the narrative that a woman’s worth and success is measured by her relationship status, sometimes I wonder if we’ve overshot the mark. That we’ve traded the shackles of one story for those of another. Disavowing my feelings is not a marker of feminist progress, but self-oppression. How I interpret my feelings is a choice. Instead of understanding my urge for connection as a character flaw, perhaps it is a sign of abundance. Perhaps I am so content on my own that I’m moved to share that contentment with another person. But this interpretation, while lovely-sounding and true some of the time, is still not true all of the time, and that has to be OK too. To think that we are either always wanting a relationship or never wanting a relationship, that singleness is pure joy or pure desolation, that these exist in opposition to one another, is a problem.

This past summer one of my dearest girlfriends and I took a roadtrip to a friend’s wedding. We hadn’t seen each other in over a year and so we filled our time catching up on every aspect of our lives. When I inquired about her romantic life, she insisted that she was so relieved to not be a relationship. That she had never been so happy, that she felt so whole, so complete, so not-in-need of a man. I knew what she meant. I knew that, like me, she cherished the way one can be utterly herself in the absence of a partner. She was not lying when she told me how happy she was, but I also knew her feelings had to be more complicated. That she was leaving out the other half of the story. And I couldn’t shake the suspicion that she was telling me what she thought I wanted to hear. As she valiantly toed that feminist line, I saw myself echoed in the creases of her brow, the uneasy quickness of her words. I started to realize that the validation I craved had less to do with permission to be single, than permission to be lonely. To acknowledge the whole spectrum of feelings that accompany singleness, not just the ones that feel good. And I began to feel sad because it seemed I’d created a space where one of my closest friends might not feel comfortable sharing her vulnerabilities. My typically pro-single rhetoric may have come at the expense of true intimacy with her. Had I led her to think she had to shirk any desire for partnership in order to be a Strong Independent Woman? Had I given her reason to believe she couldn’t say those words that were often on the tip of my tongue too: “I’m lonely”?

It was then that I fully appreciated the courage it took for Amy to share the truth of her situation, which must have been all the more challenging in the face of her younger, doting sister. (We have another sister, and even though she’s only two years younger than me, I still have a hard time letting go of my “big sister” emotional armor.) It’s only now, four years after Amy turned 40, that I see the true strength in what she said, in her willingness to be real and vulnerable. What actually inspired me about her was her authenticity and honesty, regardless of how that manifested itself, and especially in times of doubt and hardship. That was what made her a badass. Not how she checked-off the boxes of feminist criteria, but how she listened to and acknowledged her own truth.

Loneliness is the raw underbelly of being single. As much as I love hugging the corners of my mattress at night, the pockets between the sheets can be as chilling as they are liberating. I can’t pretend anymore that being single always feels empowering. It doesn’t. But ignoring those feelings isn’t empowering either. Perhaps the best way to puncture its sting is to just let it be, without judgement. To see it. Not as something that defines me, not as something I have to fight or change, but as something that just is. The urge to validate myself wasn’t really about whether I was happy single, it was about denying the reality that being single can’t be boiled down to a single emotional experience. In retrospect, that’s an embarrassingly obvious truth. I had indeed been constructing the master’s house to validate myself by tearing it down, just not in the way I originally thought. Now I’m learning to be comfortable with letting the bricks lie.