The Insanity Of Being Single

This sh*t is crazy.

Me. A very long time ago.

I dated a blonde boy once. Years ago. A tall blonde who sometimes wore glasses, knew how to build things, could keep up with me in conversation and used to play guitar in a band but now had a real job and a mortgage. I would have ordered him off a menu.

Back then flirting happened throughout the workday over Instant Message. Do you remember that? What an unproductive year 2008 must have been. Every time I’d dig into a task there it would be, the optimistic brrrring! on the screen tempting me with something much more entertaining than…you know, work.

In a sense we were spending our days together, constantly in communication, getting to know each other and developing an attachment, a reliance on that person always being present on the opposite side of the screen. He was funny, but witty funny…smart funny, my favorite kind.

I felt consumed by thoughts of him. These thoughts had power, and potential. It was so rare for me to think of someone in terms of an actual future. Looking back on it as an older, wiser, saltier woman, I know why I wanted him so much. He made me.

He brewed my affection for him like pour over coffee, tending to it, feeding it. He seemed so into me, that there was no visible reason for me to be cautious or apprehensive about developing real feelings. It wasn’t an ill-advised whirlwind romance, it was patient, and easy — I never wondered if he felt the same for me, he always made it clear. I so rarely felt safe in liking someone, and he was doing his damndest to fortify my heart.

One Chicago summer night he took me to a barbecue, a patio affair with string lights and all of his close friends from college. Until that point I’d had very few relationships (still haven’t) that involved meeting someone’s friends, and while he and I hadn’t had a state-of-the-union discussion to establish exactly what we were, the invitation to this event was another confidence-building move. I wish he’d just gone by himself.

It was one of the best nights I’ve ever had. A beautiful spot, people who were actual grown-ups. Confident pairs who, within 2–3 years or so, would all have kids. They were friendly, warm people who looked happy to see me, happy to see me with him. More than that, even. They seemed relieved. They looked triumphant that this guy was dating someone who dressed like she owned an iron and could carry on a balanced conversation and had a graduate degree. It appeared I was somewhat refreshing.

It wasn’t just my interactions with his friends that were so positive, he was right beside me. Holding my hand, laughing at my jokes, filling me in on the best stories this crew had amassed over the years. This wasn’t just a fun night, it was a good night— for both of us. When we left, as we walked down a stairwell he stopped one step below me, turned around, and kissed me. It was a genuine, happy kiss, like we’d just accomplished something. The kiss felt like a high five. I doubt he remembers it, but in my pillbox of positive male moments, that one sits near the top.

I didn’t hear from him for a couple of days afterward. I thought it was odd given the place I thought we were in, so I made plans to go over to his house to hang out for the evening. He seemed lukewarm about seeing me, none of his usual Golden Retriever-esque positivity. We sat in his backyard at sunset, I didn’t have to wait for it long.

“My friends really liked you.”

“That’s great, I really liked them, too.”

“No…they really liked you.”

It was his tone. He wasn’t congratulating me, he was accusing me. As if my behavior had been part of a plot to win over the friends he had asked me to meet. I was suddenly a grifter, falsifying a personality that attracted new friends in pursuit of ending his bachelorhood. He wasn’t going to let me get away with being awesome.

As he said the words he looked like the muscular hand of relationships was clutching him by the throat, scaring him senseless, while a kind, smart, pretty girl sat across from him in a sundress. I had never felt anything other than desire and affection from him until that point, but sitting across a plastic backyard table where our Goose Island 312s were getting warm, he felt like he was carved of ice.

He wanted me to like him, he wanted me to like his friends, he wanted his friends to like me. And once I’d accomplished all that, I was punished for it. In a lightbulb burst, he didn’t want me anymore. I didn’t understand it, I just knew that I’d done everything right, and had therefore done something terribly wrong.

I actually liked him. I probably loved him a little. It had been building for months, and it was hard to release. We also had a lot of mutual friends, so there he always was. I’d see him out at the occasional rock show, have stupid, desperate, drunken sex with him every now and then receiving the kind of affection a man might reserve for a fly swatter. But I missed him. I could never figure out why he was so scared to be happy with me.

Sometimes things happen in life that feel cruel in the moment. But now I know that what came next happened to make me move on, to force me, and many years later I’m very grateful that it happened: One autumn night at the Empty Bottle, I had to watch him meet his wife.

A friend dragged me out to a show when I was feeling exhausted, but I was still in my twenties so I went. I didn’t know the blonde boy would be there, but my friend did. My friend also knew his future wife would be there, too, and had fully planned on introducing them. In fact, I think he invited her, too. I don’t think he was trying to be mean to me on purpose. In the long run, it was for the best.

In between songs, my friend walked Future Wife over to Blonde Boy, and introduced them, inches from my face. It was one of those purposeful introductions where everyone knows why it’s happening. I had to watch their eyes meet when they said hello and I knew. I thoroughly knew. I managed not to visibly break, and disappeared home without anyone noticing I’d left. They’ve been married for years now. She’s really lovely.

There were more weeks of sadness and pain but at least that was the night they peaked. I’d eventually get over him and move on and move away and be grateful that my life looked exactly the way it did, and that he wasn’t in it. But the real “seriously?!” moment I’ll never get over is the knowledge that in any room I wasn’t in, on any night I wasn’t around, that’s when he could have met her. Literally millions of variables could have netted out a different sum. But it wasn’t enough for him to find everything I wanted him to find in me, in someone else. I also had to watch.

Being a woman comes with an assortment of challenges and difficulties. But being a single woman is fucking insane.


Single women are crazy. I’ll wear that badge. But not crazy in the societally depicted manner. We’re not obsessive, desperate, on a schedule, arriving at first dates demanding semen samples and current bank statements for review. We’re not society’s little lunatic leftovers, saving nail clippings and breeding rare feline colonies, screaming “where is my suitor?!” at the wall for hours.

Being a single woman is another kind of insane altogether, and you can’t understand it unless you actually are a single woman. And I’m talking single, for years now. Single well past the age you thought you’d be, when it feels like those nightmares where you’re late for a test. Single for enough time to learn how to put on bracelets one-handed. That’s what it takes to understand this state of mind, because this isn’t a headspace just anyone can grasp.

We earn our crazy, thank you.

The blonde boys are only a piece of it. There are so many things we encounter in single life that make no sense, are offensively unfair, or simply just sad and infuriating. Once you have 50 of those sad/infuriating things happen to you, you lose a marble or two in between the couch cushions.

The pursuit of no longer being single (the part-time job formerly known as dating) is insanity. It’s a fruitless struggle, an endless quest to nowhere, life’s little hamster wheel. And it’s dangling life’s most tempting carrot in front of our faces at all times: love. So we keep spinning, trying to get somewhere, usually just getting lewd photos and 5am requests for blow jobs instead.

Somewhere along the internet we decided to adopt a form of dating so lazy that it requires little more than the joint of your right thumb to participate. We physically and mentally distanced ourselves from dating so much that we’re essentially just one step above doing nothing. A passionless process where we barely have to think, much less develop feelings. Swipe, swipe, swipe.

For me, the core of dating’s insanity, the thing that really makes me feel like the Mad Hatter is at the helm, is that dating is an activity where effort does not match outcome. We’ve always known the equation: time + effort = result. Hooboy, not here. Not in dating. Here, time + effort = spatula. Does that not make sense to you? Welcome, now you’re gettin’ it.

Dating isn’t a climb up a professional ladder, it isn’t like learning and practicing a new skill. No matter how much you date, no matter how much effort you put in, variables you employ, it is still possible, if not probable, that you’ll end up with nothing. At least that’s certainly been my experience.

Eleven years. ELEVEN YEARS I dated, online and in real life. Eleven years of effort invested, zero results recouped. Can you imaging doing anything for that long without achieving your desired result? Do you think you could retain your sanity? Seriously, imagine looking for an apartment for 11 years without finding one.

Those 11 years are actually just since my last relationship. I have even more dating years under my belt. I have always been an early adopter of technology, and I was certainly one of the earliest adopters of online dating. I went over to a friend’s apartment when I was in Law School in Los Angeles in 2005 and she helped me create a profile like we were playing with a new, illicit toy. We ordered Thai food and watched Grey’s Anatomy and decided to see if this thing could find me a boyfriend.

Back then online dating was weird, dangerous, desperate, and all other sorts of unsavory terms society assigned to it before it became the norm. It really says something about the way single woman are made to feel about themselves. Back then we figured the chances of me finding love or being thrown in some guy’s trunk and driven out to Joshua Tree were about 50/50, and we liked the odds. Apparently anything was better than being single.

Eventually society changed its mind and decided online dating was okay because it was a tech-ified version of a thing and we were super into things being taken out of the world and put on an iPhone. The app version of anything was assumed to be better than one in real life, viewed as inherently more efficient. Online dating was there, it was an option, an apparent shortcut to love for all of us who were “too busy” to find someone the old fashioned way, which was through friends or colleagues or at someone’s random birthday party.

My unique perspective as a human being who has been using online dating so long that she’s seen it go from new, frowned-upon act of desperation to everyone’s go-to piece of advice allows me to claim the following: I also believe that online dating grew in popularity because it is the easiest way to give a single woman advice and feel like you accomplished something when really you’ve done nothing at all. People love being helpful.

“Have you tried online dating? What about that? That might work.”

Married people are so cute.

Actually, no…it won’t. Not for everyone, not for me. Instead what will happen is I’ll try every app, every photo, every bio description, every messaging tactic and still, after 11 years, I won’t have even had one relationship come out of the festering bog of ones and zeros that we call online dating. It isn’t online dating. It is nothing more than face swiping into the abyss.

But it’s there, it’s an option, it’s a way to meet people. And for single women over 30, a “way to meet people” is solid gold.

Being single over 30 is isolating. Hell, being a human being over 30 is isolating. Past the years of college or grad school, when friends are packed in all around you like balled up socks, it gets really hard to meet new people. There are colleagues, but they’re…work people. They’re a finite number of humans and we’re separated from them by a wall of professionalism and a desire to keep our jobs and pay our rent.

Honestly, as a grown up, how do you make new friends? I know I’m not alone on this, I have Twitter. We’re all wondering the same thing, convinced we maxed out on friends after college. And once all those college friends have kids, you never see them. Maybe you’ll have dinner with a group that includes some new people on occasion, but that actually turns into new friendships about as often as you replace your Brita filter. And if meeting new people you don’t want to see naked is tough, imagine how hard it is to encounter your partner.

Where do I find him? I’m honestly asking, heaven knows I could use the advice. The lies told to single women about where rich hunting grounds might exist, the seemingly normal movie scenes that actually amount to fairy tale, I’ve heard them all.

“Take a cooking class!” (All couples.)

“Volunteer!” (Single men don’t do this.)

“At the grocery store!” (Sure Jan, I’ll just hang out in the cereal aisle for an hour with a net.)

Men don’t “do” things, let’s not be coy. There are zero single men sitting at home right now with streaming TV and video games that look like real life and more free porn options than there are books in the library of Congress and thinking to themselves, “you know what, I’d like to learn how to make pottery.” It’s simply not a thing that happens.

But there are people who do see results from dating. Online, in real life, things happen to them. They’re the stories we’re supposed to use to open up our beliefs and quell our cynicism and remind us that there’s still the possibility of love in this life. There’s a name for them actually, they’re called: everyone else but me.

It feeds the crazy. My madness wants for nothing. People love sharing the success stories. “My coworker’s sister was single for like eight years, having the worst time dating, and then all of a sudden, she met him!” It’s always all of a sudden, out of nowhere, as if he was left on the doorstep in a giant basket. There are no replicable situations, no tidbits of information that are going to genuinely help me in the future. I’m just left sitting across from someone I’m sharing grilled octopus with listening to stories that bring me no closer to my goal, but really close to someone else’s.

How is a story of someone else’s happiness supposed to make me feel? And why are these the “success” stories I’m fed? People can’t wait to tell me stories of women meeting their partners but I never hear stories about their single friends under any circumstances other than when they suddenly weren’t single anymore.

Why are there never success stories with a single female lead? Oh that’s right, because the stories about single women alone, no matter how wonderful, always have a sad ending because you know…she’s alone. Promotions, amazing travel, creative pursuits, all single woman stories end the same sad way, until we end being single. Because that’s the only good ending we’re allowed to have.

I’m super happy for these “success” stories, mind you. I do want any single woman who no longer wants to be single to find exactly what she’s looking for, but I need a little more insight. The details, not just about how two people met, but how they connected themselves together rather than just having two drinks, walking home, and never speaking again as I’ve done for about the last 70 dates I’ve been on — that’s what I’m after. I’m thrilled for these “how they met” stories. But I’m still trying to figure out why “they” is never me.

One of my favorite little moments of madness is what I call the Bucket of Nothing. It’s this super fun game where I swipe swipe swipe swipe for like three days and then I match with someone, which should suggest that they’re interested in meeting or at least speaking to me. Then after we match, I send an initial message, and then…they never say anything back. Ever.

And then I ask, from my padded cell, what is the point? Why bother with the swiping? Why bother having the app? Do they just enjoy looking at women’s faces with an opportunity for a little rigorous thumb work? Why bother swiping right if they’re not going to speak to me? My mind is in such tatters it looks like the contents of a jar of glitter that has fallen to the floor. This void of nonresponse hasn’t happened once, twice, or even three dozen times. We’re in the hundreds now, baby. A big Bucket of Nothing.

It wasn’t always this way. I think people actually spoke to each other in the flesh at one point. I think it was the 90s. I think before the idea that you could meet someone without leaving your couch or putting on pants and deodorant became an option, people had to work for companionship. We’ve now completely streamlined the process, removing all toil required. The Industrial Revolution of Dating. I’d like to take a flamethrower to the factory.

This dehumanization of us, this creation that’s turned single women into nothing more than one of millions of faces populating apps that don’t give a shit about anything other than how many of us they can advertise to, generates some low feelings. I often think of modern dating as essentially a conveyor belt of menu morsels rolling by. There are always more options coming, and online dating makes me feel like I’m nothing more than one.

In being single, I want to feel like a choice, not an option. It’s a hard value to hold onto, when the entire modern dating landscape tries to convince me of exactly the opposite. But what’s more important to hold onto in the face of dating insanity than our own self worth?

We’ve been taught to hold onto the “hope” that we’ll eventually meet someone and be happy. But what if instead we held onto the truth that we’re allowed to be happy right now? That we’re worthy of being happy right now? I think we should dedicate effort to not giving up on ourselves, versus not giving up on the idea of “him.” The ROI on that seems better, call me crazy.

The definition of insanity is repeating the same action over and over again and expecting different results. And I’m a grown, conscious woman with a sense of logic, so fine. I’ve been doing this over and over and over and thinking…what, eventually it will work? Like the dating gods will just get tired of me and say…fine, give her one? If dating isn’t working, why do it? Why waste my time? I’m not crazy, the hell with this.

But when I stop, when I walk away from dating, I’m overwhelmed with the feeling that I’m not contributing to my own happiness, that I’m letting this single state happen to me rather than taking productive steps to end it. My partner isn’t just going to fall into my lap. I’ll never meet anyone if I don’t try.

It seems like the burden is always on me. To put in more effort, explore more avenues, figure out the puzzle already. But this puzzle is fighting back, and there’s never any burden on anyone else. The dating apps never have to get smarter, the men on them never have to know consequences, the blonde boys will always do to me whatever the fuck they want.

And the insane societal message I receive is: Yes—all of this nonsense is going to keep happening to you, but you’re not allowed to give up. Because if you don’t put in effort, you’ll keep being single. And if you do put in effort, you’ll be single then too. And being single is bad and wrong. You are bad and wrong. People will convince you they want you and then throw you away. That’s probably your fault. Apps will show you a million men and you can’t have any of them. But keep swiping anyway, because we made this for you. It doesn’t work, but we made it for you. Fix your single, fix what you are, because it’s broken, you’re broken. We don’t have a way to fix you, but we know you’re broken. You’re getting older and less pretty and soon no one’s going to want you. Even though no one wants you now, either. What are you still doing here? Go, go find him, we don’t know where, we can’t help you, just find him, somewhere, you should really try. You should really try to not be single. It’s very bad, what you are. You’re bad, single girl. You’re wrong, single girl. Go, go fix you, we don’t know how, just try.

We’re all a little mad in here.


Thank you for reading, thank you for sharing. If you liked this, you’ll probably like , too.

NPR once called me a humor essayist, let’s go with that. Host of A Single Serving Podcast. shanisilver[at]gmail

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store