The first time I signed up, it was because I wanted to know what the fuss was about. I answered hundreds of questions and uploaded flattering photos. Crafted a witty bio, listed my favorite things in the categories of music and films and books and foods. I made my profile on the dating site and I promised myself I’d give it a week. Technically, I lasted five days.

My husband and I had opened up our relationship during the thick of the worst of Lev’s cancer treatment. We wanted to keep living together and to stay married as long as we could stand one another even if it meant quietly screwing around. Don’t ask, don’t tell, we said. How modern of us. Turns out, we both unwittingly joined the same online dating site. Because of course we did. The site immediately pegged us as a 98% match (exhausting!) and my husband messaged me within hours of my putting up a profile. I blocked him. In all fairness, I blocked a lot of people. In my recollection, my first stab at online dating was a non-stop barrage of attention from men who felt they knew me from a few photos and my carefully chosen words. The tone of blithe familiarity from these strangers was the same kind of unpleasant as a bug flying into your mouth while you’re walking. No self-awareness. No grasp of manners or self-deprecation or ice-breaking. I was too good for this nonsense. I had too much dignity. Not to mention, the prospect of meeting new people, of having to remember which things about my life I pretended to love and which parts I was allowed to openly hate, threatened to expose the sham of my existence quite handily. I couldn’t seem to get to the humble place or the shameless place. Just couldn’t get there.

Though I very much wanted to be ready, it was clear to me that I was nowhere near prepared to date; to explain to these probably perfectly nice men—who simply wanted to have dinner with a pretty girl and maybe feel her up—that I was separated from my husband, but we were still living together b/c our child was dying. After five days of feeling intense pressure to commit to an actual date with any number of strangers who seemed sort of okay, I shut down my profile and went back to hiding on the Iconoclast’s couch. In the wee small hours, I’d talk to him for hours about everything that scared me. He’d talk me down and then we’d screw till I was calm and calm and calm. At the end of my world, he was my fallout shelter.

I am way more attractive at 36 years old than I was as a teenager or in my 20s. The angles of my face have gotten sharper and the curves of my body have grown softer. I am dotted with a map of tattoos, mile markers of the things that have shaped me. My deeply ingrained awkwardness is well-mitigated by sexual confidence. I am certain that despite the near total ruin of my life, this is the best I’ve ever been. Humility, however, is not a quality I would ascribe to myself. I am vain and a know-it-all, dyed-in-the-wool.

The second time I ventured into the online dating pool, it was because I wanted to be humble. I had messed things up with (or fled from) all of the men I loved, the ones who’d loved me, and all of the men my friends had introduced me to. I was sick to death with myself and with the optimism of maybe-this-time. I had proven whatever I had to prove (mostly I proved I was excellent at hiding behind an armor of snark and disdain). Now I wanted to be quiet and docile and do things like everyone else. I needed the comfort of an algorithm, some kind of statistical formula that made it at least likely that I might jibe with some man in particular. I wanted to make statistical sense of it all.

Online dating is a unifying, homogenizing experience. It’s one of those things that, no matter how rich or posh or cool you are, you can’t send a minion to do it for you. You have to show up and be counted. It’s like the DMV. You are just like every other sad, broken socially awkward person you judge as you’re scrolling through your reject pile. And odds are, you’re in someone else’s reject pile. You’ve taken the time to make a profile on an online dating site and that makes you—in essence—just like the fat guy in the tank top and neon orange sunglasses holding a fish/deer/other dead animal he just killed. You’re on par with the guy in military fatigues who may or may not have shot his profile photo at Abu Graib. You hope, just like they hope, to be someone’s perfect match. Or maybe you think: It can’t hurt. And maybe, probably, it can’t. You belong there with everyone else simply because you made the choice to show up and be counted.

In version 2.0 of my online dating adventure, I made dates. Lots and lots of dates. I strategically set them up sometimes two per night to meet as many people as possible. To be open; to really do it. I met some lovely folks and some less lovely. Consider these, a selection of guys-I-went-out-with-once, for your reading pleasure:

There was the rockabilly Steve Buscemi, who I met up with once at 1 a.m. for one drink. Tattooed from neck to fingers, he was a touring musician. He teared up when I told him about Lev. We made out for a minute by the car. Sweet, but not for me.

He was followed by the guy who wrote freelance math problems and insisted intelligence was not a quality he valued in other people. He was in a competitive karaoke troupe and took the bus because his Mercedes was rusting out on his front lawn. We had lunch. I dropped him off afterward. We had no chemistry.

I ate a Cobb salad on my date with the former Mormon. He and I traded mixtapes (I still listen to his). I was impatient with his niceness which bordered on pandering. He was tortured about his ex-wife. Too soon.

The man who wore clogs to our date was a builder in his late 40s, depressed that his wife had left him after he’d constructed her dream house from scratch. He told me he’d biked through the sub-Saharan region in his youth and it seemed to him that every woman in Africa has a dead baby. He tried to kiss me.

The one I called Bright Eyes was cagey. We met up once in the evening to eat and drink and make-out (and once more in the afternoon because good chemistry bears revisiting). We were pretty much done after that. Though I proceeded to run into him no less than 10 times around town. With my kid. With my friends. With other dates.

The only man I dated more than twice showed up on my page a few weeks into my odyssey of online dating—an attorney who rode BMX bikes and built bike trails for fun; good looking, clean-cut but rough around the edges. We traded a few emails. He was a decent writer, not super witty, but he kept up. I was drawn in. At the end of our first date, he kissed me goodnight and there was a spark. Right there is where I got mind fucked by good on paper. Because with online dating, you’re invested before you ever even meet the person. You’ve invested time poring over their photos and texting back and forth and telling all of your friends about how perfectly their music taste matches yours. And if you’re me, once you meet the first halfway decent person in a month of trying and he gives you one good kiss, you give that person six too many chances.

Good-on-paper and I alternated planning dates. We saw music, ate great meals and attended culturally significant events in museum lobbies. After our third date, I found out that—in addition to being good on paper—he was also good in the sack. Somehow, though, on every one of our dates, even the ones I’d planned, I was maddeningly bored. He talked about nothing but hating his job and BMX and when I tried to lighten things up, it always seemed to me that he didn’t quite get my jokes. He would say: “Ha! That’s funny.” But not laugh? It seems Mr. Good-on-paper was a good time black hole. So the world class burlesque show bored me to tears. The reading of my favorite author (to which Good-on-paper showed up on his motorcycle) was a total snoozefest. I just kept thinking it’s GOT to be ME. He’s a lawyer. He rides BMX bikes and does tricks! He doesn’t have a roommate! Or an ex-wife! He’s so rare. Like a unicorn. I tried to make it work for two months.

Eventually, he asked me to help him redecorate his place. And I realized that he wanted to see more of me than I wanted to see of him. It seemed like a fitting time for an exit. I broke up with Good-on-paper without tears or even sadness. But I was discouraged. He was the only one out of all of my many dates who even threatened to have any potential whatsoever. We tried to have a drink after we stopped seeing each other, but it was a (boring) mistake. At the end, he tried to get me to come home with him. I had an early flight out of town in the morning and I was in no mood to relive the magic of rolling around with the past. I went home happily alone and took a much-needed break from treading water in the online dating pool.

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A week after my comedy debut in St. Louis, I’m on vacation in Los Angeles, visiting the offspring of my friends. (Like salmon, all of my friends spawned at the same time and during that five day sojourn in L.A., I visited something like eight babies of people I knew—all under 18 months old.) I’m holed up in my friend’s rambling Victorian house in Echo Park getting ready for dinner when a particularly clever message comes in via my phone’s online dating app.

I look up this clever fellow’s profile. His writing is wry and spare. He’s heartthrob handsome in his photo—jacket & tie, sandy brown curls, downcast blue eyes—but with the saddest face. It breaks my heart a little. I don’t message him back right away, but I do eventually. And we meet. He’s drier than dry. Funny. Razor-sharp. He’s cute and floppy haired and sullen like the boys in the posters on my high school bedroom walls. And his face in person—as on his profile—is sad and so worried. But in the rare moments when he smiles, his face opens like windows. It takes my words away. I see him again.

If the Iconoclast was my fallout shelter, this melancholy boy who found me on the Internet was waiting for me, hand extended, when it was safe to come outside.