Street Smart Chicago

Cereal Romance: Adventures in the Brave New World of Online Dating

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Illustration: Beryl Chung

By Michael Workman

Breaking up is hard to do. It’s made even harder when it happens in the grip of a new social reality. I’m sitting on a window barstool at Café Selmarie on the Lincoln Square strip, where I’ve been summoned via text message through a flash downpour for the bad news, and I’m totally blindsided. How did this happen? It’s absurd, something out of an episode of “Bored to Death”: just three days earlier we were lying in bed discussing plans for a friend’s wedding two months out. I rotate my gaze floor to the ceiling. What did I miss? Everything slows down, then pauses a beat. My clothes are dripping wet, and I’m sitting with (let’s call her) Ramona, who I met through an online dating site called OkCupid. It’s a service I’ve been on for nearly two years now, since my wife and I split up (amicably) and after hundreds of therapy sessions, when I found myself confronted with a dating scene that has changed pretty radically. Almost ten years ago when I was first married, a few friends used to tell tales of trolling the personals section, a site that’s tumbleweed town these days. Then came Friendster, Myspace and finally Facebook, and social media has transformed online dating into a community experience unrestricted by geography or class. OkCupid,, eHarmony, all were profiled in a recent New Yorker piece that lays out the history and precedents of these dating services without describing the personal experience of using these sites (the author couldn’t do any actual dating, since he’s happily married, so he had to resort to interviews). It’s all legit now, and if you’re in your early twenties, it’s so accepted, it’s passé to debate. And not to mention the BDSM-themed FetLife, JDate for Jewish paramour-hunting or any of the hundreds of niche dating communities (I even have friends who are amusingly advertising for a “third” on a Christian-themed site). As a forty-year-old single person with a seven-year-old son, a devastated bank account courtesy of the fucking recession and the transition back to a single-income household, with few friends left who haven’t moved away or holed up in their own versions of family-life house-arrest, it’s a world that makes me feel like an eighties guy beamed into the future with a closetful of bad fashion. It’s all new, and I stand out like a sore thumb.

Ramona and I date for an intense roughly ten or so weeks at the start of the summer, and she repeatedly insists we define the relationship very early on, in the first few weeks. I’m confused by her sense of urgency but am in the mood for a real relationship after a string of disappointing one-offs, so I didn’t mind making it formal. It helps that we’re both into S&M and kink, and the honesty of our boundary negotiations feels good. Shame is relegated to the status of a foreign concept. We’re empowered by our mutual honesty: it’s all about openness, and constantly tweaking our self-awareness, identity choices, sex and play preferences to suit the other. We start to experiment with unrestrained zeal. She likes for me to slap her face while she’s performing fellatio. Hard. I mark her entire torso, thighs to neck, with the flat of my palms and a metal-tipped riding crop trying to get a “red dress,” leaving hand-patterned purpling hematomas that welt and fade into splotchy patterns of bruises the color of subcutaneous dried blood. She arouses me effortlessly. I yank her hair during anal pony play, splayed out on the floor, biting her abdomen hard enough to cause minor muscle damage. She likes me to threaten to burn her with cigarettes. Call her my slave. Rip out handfuls of dark black pubic hair during hour-long, marathon masturbation sessions. Fill the bathtub with water afloat with body soil and hold her head under in my fist until she can’t breathe and starts to flail. Life is good, and entertaining. Our toy collection grows to include some heavy steel butt plugs, his-n-her insertable vibrators, a nasty pair of nipple clamps with corrugated forceps hinges. Surgical needles. I tell her we have to watch Polanski’s “Bitter Moon,” and we spend hours trading discussions about our favorite cultural markers. We make the rounds at local dungeon parties and start advertising online for play partners. Craigslist Personals once again proves it’s still an effective place to meet horny strangers.

We spend weekends together at hotels in Lakeview, where I dress her up like a man, making out on the dance floor at Berlin past three in the morning. She’s on an impressive regimen of psychopharma, including Lamictal and Adderall, basically an artificial form of adrenaline in pill form. We bond together over Stephen Elliott’s “Adderall Diaries,” and she shares the little blue ten-milligram pills with me. I can only manage two and a half or five milligrams without developing a case of the shakes, and can’t take it regularly without developing a persistent nausea. We spend nights talking until the sun comes up about Habermas and art patronage, Judith Butler and BDSM scenes we’d like to try. We go to therapy together as a couple. She’s intelligent, more wellness-aware than anybody I’ve ever met, constantly critiquing my drinking and cigarette smoking while filling the room with pot haze. It’s high-maintenance, but I like it. After each BDSM scene, she critiques my aftercare, terrified of getting trapped in a subspace of intensely pinched depression. Pretty quickly, I start to fall in love with her, and tell her so. She tells me that she loves me, too. Our lives start to bleed into one another, the sharing of friends, introductions to family.

My experience with Ramona stands in somewhat marked contrast to my other dating experiences, almost all of them online and mostly through OkCupid. There’s the twenty-eight-year-old artist with the pixie cut who I had passive vanilla sex with in her studio bedroom beside piles of cut paper swatches for her “painting drawings.” There’s the frumpy blond-haired architect who, on our very first date, announces that she’s only interested in finding someone to have a baby with, suggests we trip on mushrooms together and then stops answering my calls and text messages when I don’t call her while away on Thanksgiving. There’s the industrious Kansas City transplant who works as a theater audio engineer and has a friends-with-benefits arrangement with five other guys. These sites have also, surprisingly, become a place for striking up new friendships, among whom I count a polyamorous animal biologist and a twenty-year-old language student who moved to Argentina for a year of study abroad. I met them all online, including a lesbian couple with whom I was in a relationship last summer. They lived in a Hyde Park high rise at the time, and one of them was a nurse who I let insert a long surgical steel probe down the length of my urethra. They broke up after twenty years in an exclusive relationship together when they both decided they wanted to be involved with men as well. One of these ladies is still a very good friend of mine, and remains an ardent adventurer in modern love.

Online dating has made it much different out there than I remember it from single life in my twenties. But how it has really transformed dating is that it’s redefined the process by instilling a sort of informed consumerism, the amorous equivalent of eating only organic-farmed vegetables and free-range chicken. It goes roughly like this: a) the more specific you are in how you think what you say about yourself will appeal to an ideal partner when filling out your profile self-description, interests, answers to user-generated questions, what you do on a typical Friday night, etc., then b) supposedly the more accurate the “secret formula” each of these sites uses to statistically generate your compatibility will be, resulting in c) a more likely successful pairing. No muss, no fuss. Conscience clean, life values successfully correlated and matched. That 99 percent compatibility rating at the top of the profile you’re browsing is meant to indicate that, through the magic of online dating, you’ve managed to discover that mythically elusive, individually tailored, nigh-perfect match just for you.

Except it doesn’t, because it’s all just on paper. All of this is to articulate that these sites, in this writer’s experience, have a similar design issue, written about over the past year by literary luminaries including Zadie Smith and Jonathan Franzen, whose recent essays on the subject more or less boil down to the fact that the virtual will just never be able to supplant or at best enhance the splendor and infinite complexity of real life. That is, the internet and its consuming “social networks” have functioned to fundamentally redefine our sense of how we interact as human beings, with some pretty serious limits built into these new models of our own self-perceptions. People have only recently, it seems, come to a definition of what you can and cannot say on Facebook, for instance. It’s considered somewhat unseemly to post anything with any real troubling human emotion behind it in a status update, preferring instead an information-sharing protocol of news and homogenous, largely sterile personal preoccupations. Similarly, the experience of browsing through the scrollable page after page of usernames and profile photos on, OkCupid and eHarmony is an experience not unlike browsing through aisle after aisle of cereal boxes. Indeed, you’re not meeting a person, as Chris Rock once brilliantly described it, you’re meeting their “representative.”

As a caveat, I’d like to state for the record that there are some notable good things that have come out of and been usefully propagated in this environment, such as the new concern with gender identity definitions (as opposed to sexual identity, mind you), and the new ability these sites give people to meet others who just flat-out exist beyond the reach of their usual social circles. But in this self-idealized world, if you pay any credence to recurrent concerns voiced in a vast cross-sampling of online profiles, it sounds as if people are overwhelmingly obsessed with such critically pressing shit as moustache memes, craft-brewed beer, ziplining across jungle canopies, and the noble notion that potential mates had better goddamn well know the grammatical difference between “their” and “they’re” and “there.” Or… maybe it’s just another example of commodification and homogenization, the introduction of a new form of dehumanizing and depersonalizing groupthink like, for instance, that which took place in the early nineties to consolidate the media. Except that now, transparency has risen as a value in the culture of our public lives to such a degree that it almost eclipses the concern for accountability. A deleterious result of media consolidation, to stretch the analogy, is that it’s hard to find good coverage of any local news, it’s all just too big-picture, too centralized and lacking in the informed context of a lived environment. Debates take place cloaked in anonymity on comment threads, infinitely parsing each other’s meaning to the point of meaninglessness. Even our notions of intimacy have been transformed by this new way of relating to each other, applying this depersonalization to our very human need to fill that felt void in our lives with someone we can love. It’s the long-standing problem of life in a viciously atomized society, now available for even your most stubborn relationship needs.

It’s about 8:30ish at TGI Friday’s on Erie about twelve months ago. I’m sitting at this roundabout bar jammed with thrill-seeking tourist couples, deflated businessmen and a roomful of guys in hoodies and sneaks waiting for Sam Yagan, the CEO of OKCupid to arrive. It’s like OkCupid exploded and all the people in those hundreds of profile photos have just spilled out into the restaurant. Suddenly, they’re all actually… real live people! Service men and women in the TGI Friday’s uniform of white shirts and black slacks or skirts dash around trying to handle all the beefed up volume in demand for alcohol. Given that it’s all on Mr. Yagan’s credit card, there’s an active speculative debate along the bar rail of what counts as the restaurant’s toppest shelf, followed by the ordering of copious amounts of the consensus beverage. Selections of high-end whiskey seem to carry the evening. That, and a cringe-worthy number of Key West Coolers and Beverly Hills Iced Teas. Lured by the promise of an open bar tab to demurely drink on, and out of a mixture of sheer boredom, irascibleness and a newfound fascination with online peer-bonding, I’m straddling the bar in a suit coat and tie, pen in hand. It doesn’t take long for the socializing to wind up to a fury pitch, and within an hour it’s an out-and-out drunkfest. The room is packed mostly with lonely guys, and the few women who identify themselves as “poly” or non-monogamous are swarmed as if they were forest kills surrounded by malnutritioned wolves. Two Goth girls out front, who have driven two hours from Indiana just to hang out with real-life OkCupid people, start working off the pitchers of frozen margaritas by puking their guts out onto the sidewalk. Not the image of all the liberated, smart-set successfulness you’d expect from the snappy profiles of the attendees. And it’s not surprising, really. Given the de facto magnitudes of distance between how people portray themselves online and the reality of their real, disappointing, hard-scrabbling yet hopeful human lives, it’s hard not to appreciate the scope of the challenge. I wend my way through the crowd to Yagan and manage to get in a few questions about the service, something about expanding the available choices to reflect the evolving complexity of different types of relationships in an era where divorce is well past fifty percent, that kind of thing. He replies that the majority of users don’t want it, and that the traditional off-the-rack marital-relationship seeker is their core audience, and in turn their core business. Again, it comes down to dollars and cents, business and the culture, the tug and pull of evolving social mores and the bottom-line mandate of people with something to sell not to alienate their best customers. Once again, a matter of the wants versus the needs, and we’ve got the dating culture we deserve.

Drenched, freshly broken up and sitting at this café on the strip in Lincoln Square some months later, this gulf-scale discrepancy between the ideal and the real quickly comes into sharp focus, and I feel it more acutely than ever before. I realize that Ramona and I haven’t actually been in love, that it has all just been a series of expectations we were living out together, a desultory, pretend relationship. Fantasy. Floating above my body, my mind telescopes through all the possible moments where I may have missed a signal, some little detail, some clue. Is it that girl she met online who wants a female playmate but isn’t interested in men? After all, Ramona told me they got physical even though she insisted she didn’t want to. But when I got them both together to discuss not respecting each other’s boundaries, she said Ramona never said it wasn’t okay and Ramona seized up and wouldn’t say a word about it. So, maybe. Or maybe it’s her blowhard ex-boyfriend of seven years who’s been experimenting with open relationships with his new wife? When Ramona and I discussed it, we agreed he was probably imagining a threeway. None of it seemed right, exactly. Then, what? When I ask her why, she simply says that I haven’t done anything wrong, it’s just that when she’s with me, she feels bad about herself.

For days later, through the unwise Facebook status update posts, the discussions with my kinky friends at the FetLife munch in Lakeview, any sense of figuring out the actual motive remains elusive, her rationale oblique. I can’t understand it. It vexes me, sends me into a deep, prolonged depression. Days later it finally starts to sink in, for the lenses to finish coming into alignment, for the realization to hit me. It’s as unsatisfying an answer as her explanation for ending it, as dissatisfying as the difference between expectation and the encounter with a fallen, harsh reality. I’m not real to her, I was never real to her, I was always just her own idealized version of who she thinks I am. Just a ghost in the online machine.

Then something else happens.

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