by Joe Berkowitz and Joanna Neborsky

It’s pretty hard to reverse engineer a meet-cute. These things either happen or they don’t. If you were really serious about it, you could probably arrange for, say, an errant shopping cart to go charging off in someone’s direction and then you could rush up behind it saying, “Sorry, sorry!” and that’s how you’d meet, but then you’d have to live with yourself for the next 50 years or so, knowing that, basically, you’re Elmer Fudd. Sometimes when a radiant single lady comes floating along the sidewalk like a dream, I think about stopping her. But I never would. It just seems as intrusive as a catcall — or an errant shopping cart. I might as well be passing out handbills for a shady-sounding sample sale. So instead I say nothing and then she’s gone. We won’t be accidental seatmates at a dinner party later. It’s a missed non-connection, a moment less significant than if we’d been on line together at Whole Foods buying the same artisanal sherbet. How-we-met stories are overrated, anyway.

When you’ve been single for longer than a pregnancy term, the people who love you start to get concerned. They begin to wonder whether you’ll ever impregnate anyone. Pretty soon they’ll ask some pointed questions about online dating. It doesn’t matter whether you’re single by choice or if you just lie and say you are, some Good Samaritan will always nominate the Internet as the answer to your problems (because you definitely have problems). Any resistance you show might stem from a previous experience with online dating, or from a novice’s view that these websites constitute some sort of Matrix of Loneliness, connecting romantic undesirables and allowing them to mingle badly. Either way, no single answer will ever satisfy the person doing the persuading. The last time I had to explain my aversion to online dating, I surprised myself by agreeing to try it out (again). It seemed like the easiest way to end the conversation.

Putting together a dating profile means performing a self-autopsy and reassembling the pieces into Sexy Robocop. You save what’s worth salvaging and shield the damaged parts with reinforced metal. You strive to find the middle ground between showing you have nothing to hide, and just showing off. You carefully curate your interests as if they were co-op displays in a Barnes & Noble, reveling in the understated complexity of liking both Nicki Minaj and My Bloody Valentine. Your picture gallery broadcasts a series of defensive messages: “See? Other females aren’t afraid of me.” “See? I go to museums sometimes and mimic sculpture-poses because Culture.” “See? I’ve been to a Halloween party so obviously I don’t spend much time alone, crying to The Cure’s Disintegration LP and drinking wine from a can.” Dating profiles reveal more about how you see yourself than how you really are, and more about how you want to be seen than how you will be.

With infinite choice comes infinite opportunities to judge. The more options that exist, the pickier you become. Scrolling through profile after profile, I am transformed into an imperial king, surveying his goodly townsfolk from a balcony on high. Those with minor perceived flaws are summarily dismissed (“Next!”) because surely someone closer to the Hellenic ideal is just around the corner. Anyone cute might be cast aside for the smallest breach of taste: a penchant for saying things like “I love life and I love to laugh” or self-identifying as “witty.” Yet even when I genuinely find myself attracted to someone, I’ll still react with skepticism. What’s the catch? What dark and terrible secret causes her to resort to this thing I am also doing? After scanning closely for red flags and finally deigning her regally worthy, I dispatch a message. But then the truth reveals itself: the king is not her type and also he is not really a king.

Messaging strangers on a dating site is a great way to dabble in Glengarry Glen Ross-style competitive salesmanship. Every hot lead is sure to have already attracted a multitudinous horde of Al Pacinos and Jack Lemmons offering the same bill of goods. You’re all sharing space together in an overstuffed inbox, so words need to be chosen wisely. Asking questions about a prospect’s profile is one way to go — except she probably wrote it months ago and so mentioning her affinity for Frank’s Red Hot now seems as dopey as it probably should. Another option is asking nonsense questions, like who’d win in a fight between Matt Lauer and Brian Williams. (Advantage: Williams.) Since such questions aren’t specific to each lady, though, she’ll probably assume you’re cutting and pasting, and let’s face it — you probably are. When an opening salvo goes sour in person, you can always keep talking. Online, you just get ignored forever. You can send a follow-up later on (“Do you HATE having an awesome time with handsome gentlemen?”) but that smacks of Jack Lemmon-level desperation.

The only way for me to do this without ending up in an existential tailspin is to not take it too seriously. If low expectations can elevate so-so movies, perhaps they can also upgrade one’s dating life from a graveyard to at least a fancy graveyard with picturesque views and atmosphere and motorized carts for the infirm. But even casual maintenance of an Internet dating presence requires sending out the odd message, responding to same, and internalizing the byzantine rules about which topics are off-limits and when to take things offline. It’s a hefty time-suck and it makes it hard to keep up the illusion that this is all just a lark. But if I never get my hopes up, nobody can accuse me of being too invested in the outcome. That way, when we actually do end up liking each other, it will feel more like something that just sort of happened — rather than the result of actively engaging in an organized simulacrum of human mating rituals. “Whoops, I seem to have tripped over my laptop and subsequently bumped into you on the Internet!”

Some dates wheeze to a quiet end the moment you encounter each other in person. Then there’s still a whole night ahead to squirm through. A bad date, at least, leaves you with a fun new story about how everybody’s always a nightmare; a mediocre one offers just enough of a good time so that nobody face-plants the table. Going through the motions on a date feels like interviewing for a job you don’t want strictly to keep a parole officer off your back. The more such dates you go on, the more they echo each other and blend together into one amorphous person who’s into Wet Hot American Summer and brunch at Buttermilk Channel, but still incompatible with you somehow. Other times, it’s you who’s the problem. You say one dumb thing (“I would be incredibly easy to blackmail”) and it’s a deal breaker. The disappointment of not being chosen, however, is almost preferable to the Fellini-style ennui of manufacturing chemistry with someone whose interests map well to yours while every moment becoming less certain whether that’s what you even want.

Everyone has a friend who is so charismatic, brilliant or good-looking that the idea of him or her trolling OKCupid is mind-boggling. I am haunted by those friends. What is it that separates us? Is it gluten? I’m at peace with the fact that Drake sings about how jaded he is from being constantly propositioned by beautiful women — because Drake is crazy-famous. My friends who’d never be mistaken as online daters are not famous, but they also possess some ineffable quality that makes them forever F-able. As far as our social sphere is concerned, they might as well be Drake (or nearest female equivalent): They’re stars, and finding them on a dating site would create cognitive dissonance of Orwellian proportions. Personally, I’ve never felt as spectacularly anonymous as I have as an online dater, united with everyone else on the site in that we all have a reason to be there. I can rationalize about Internet dating for days. I can think up reasons for why the way my grandparents met is outmoded. But I don’t want any woman to think she was my last resort, and I don’t want to imagine that I was hers. When we say, “I’m so glad we found each other,” I don’t want it to refer to the way we had to find each other like hidden files in a hard-drive search.

Sometimes a person of interest will disappear from your online dating correspondence, as if whisked away by the Rapture. You just notice they’re suddenly gone and you’re left behind, exactly as Kirk Cameron predicted. The nature of online dating is ephemeral and temporary. It is designed to end and, one way or another, it will; either with a Mission Accomplished banner or an AWOL report. The longer your adventure goes on, the more you start rooting for every attractive person you meet to become the reason you will delete your profile. “I tried it for a while but then I met my lover on the subway,” is what you’d ideally say. Minus the word ‘lover.’ People always swear you only meet someone when you least expect it, which is not entirely true because you least expect it when you’re dead asleep and, personally, I’ve never been rustled out of bed by a stranger who became my new girlfriend. What if you always expect it when you’re supposed to least expect it? Relentlessly checking people out in the checkout aisle, walking down the street trying to force eye contact. Maybe then you gradually give up on Internet dating without canceling your account, and the most expected approach to meeting people somehow manages to surprise you. The person of your dreams reaches out to the profile you forgot you had, and it’s such a good fit that the way you met doesn’t even matter. It could totally happen! It just probably won’t! On the upside, I hear your grandmother has found someone perfect for you. She’s a Taurus with a soft spot for pugs, and she’s going back for her MBA.

Joe Berkowitz (text) edits books and writes stuff. He also has a tumblr.

Joanna Neborsky (art) is an illustrator living in Brooklyn. She makes books and animations about books.