The Work of Dating Advice

Here's how to find love in the age of apps, ADHD, and AI

The work never ends

The guy from my old Dallas gym tracks his dates in a spreadsheet. Thirty-seven years old, medical device sales, decent college first baseman at Seton Hall back when he was somebody, leased BMW with very low miles on it. He slacked the spreadsheet to me while sitting in the sauna last week. Color-coded columns for height, career, something he calls "ROI potential." He updates it on his phone between sets.¹

He's not unusual. I know a woman who kept a notebook with 47 first dates from last year hoping she could get a "Millennial dating novel" out of it, something on "the way we live now."² Then there’s another sad soul who A/B tests their profile photos. A marketing manager who's been "in the apps" for six years and talks about peak messaging times like they’re discussing quarterly reports.

This is dating now. Spreadsheets and strategies and subscription tiers. Everyone's got a system. Everyone's optimizing. Everyone's alone.

My best friend's parents met at a bus stop in 1978. She was reading a pocket paperback. He asked about the book, Erica Jong’s Fear of Flying. She said it was terrible but had to finish it. He said he wasn’t much of a reader but understood completely. They got married eighteen months later.

"It wasn't magic," she told my friend once. "It was just Tuesday, Wednesday, Thursday." She never read another Jong book. He never read another book, period.

Same bus, same stop, same time. Two people in the same place often enough to become familiar. No algorithm matching them, just proximity and pocket books and the slow accumulation of ordinary moments.

That world, for good or ill, is gone baby gone. Now we've got infinite choice and infinite metrics and infinite loneliness. The spreadsheet guy goes on three dates a week. He's got his coffee shop routine down to a science: 7:15 a.m. arrival, oat milk cortado, table by the window where the lighting's good. He told me the baristas are his "key demographic." College-educated. Probably have around $20k-$30k in student loans. Looking for stability and still "fecund" in Sperm Wars-ese.

He uses AI to write all his messages now. Shared his conversastions with the app bots not too long ago. You feed the AI their profile, it spits out the perfect opener. The perfect follow-up. The perfect suggestion for a first date. He's got conversations going with twelve women and hasn't written a single word himself.

"Maximum efficiency and so very, very clean," he said.

I watched him at the coffee shop with a woman who kept checking her phone while he delivered lines his AI had scripted. When she excused herself to the bathroom, he pulled out his phone and updated her status from "high potential" to "warm, follow up in Q2." She never came back from the bathroom.

The thing is, he runs into others doing the same thing. Two weeks ago he matched with a woman whose responses had similar repetitive structures, lots of em dashes, and were mirroring his original responses. Turns out they were using the same basic tier of ChatGPT. Their bots were having a token-powered, compute-conserving conversation while they sat at home, watching Netflix, wondering why dating felt so empty.

The apps were supposed to fix dating. Make it efficient. Help us find "our people," whoever those might be. Instead they turned everyone into products and shopping into a full-time job. Swipe, match, message, meet, repeat. Like factory work but with small talk and overpriced cocktails.

My old roommate matched with a woman who worked customer service for one of these companies. Three years of fielding complaints from people convinced the system was busted because they weren't finding true love. Men wanting refunds because their catfishing scammer matches weren't responding. Women sure they were being shown to the wrong people, that these grey-haired old dudes with sunglasses couldn’t be the sum total of the Southwestern Pennsylvania dating pool.

"Everyone thinks it's supposed to work like Amazon," she told him over drinks. "Like you can just order the right person. Not at all. Most people are duds, like those cheap imported products with the stupid all-consonant names."

She ate napkins. Not nervously tore them, ate them. Little pieces at first, then bigger chunks. Called it a nervous tic. My roommate said she had Grey Gardens energy, like she hadn't left her apartment in years except to go to work. Here was someone who spent eight hours a day troubleshooting why lonely people couldn't connect, then went home to nibble paper products in solitude: "I'm selling people this service they don't want, when I don't know what I need."

Smart, funny, lived forty miles away. Neither of them wanted to drive that far for maybe. That's another thing about modern dating, how everything's maybe. Maybe this will turn out okay.³ Maybe someone better's in the next swipe. Maybe if I work the Post Hand (PH) harder, try another app, get better photos. Maybe the person across from you eating napkins is exactly as lost as you are.

My cousin met her husband on Match.com in 2011. They tell the story at parties like it's a Disneyfied fairy tale. What they leave out is the Brothers Grimm reality: three years on the site, over a hundred first dates, crying in her car after half of them. "Lightning only has to strike once," she says when people ask for online dating advice. Like telling a drowning Titanic passenger that they only need to find one life preserver.

The real problem isn't the technology. It's what it's done to us. We've forgotten how to be bad at things. How to be awkward. Once upon a time not too long ago, you had to approach someone at the cramped record or comic store not knowing anything except what you could see. Had to stumble through conversations about Erica Jong’s Fear of Flying without prepared talking points. Had to invest time in getting to know someone without being able to check their LinkedIn first. It was messier. Less precise. More human.

Now everyone's got their eleavtor pitch ready. Their best stories rehearsed. Their red flags hidden like seborrheic dermatitis under concealer. I watched two people meet on a date last month, both on their phones, each browsing the memetic piggy slop in their own newsfeeds. Not talking. Just doomscrolling with their Post Hands while their Goon Hands remained hidden under the table, doing goodness knows what. They looked comfortable enough, a pair of American dreamers sleepwalking through another drowsy evening.

As for the spreadsheet guy — well, he’s still optimizing. Last month he told me about his new strategy. Something about market segmentation, moneyball, and AI-powered personality analysis. Value over replacement dater (VORD) and ultimate wingman rating (UWR). He's middle-aged and alone and can't see that people aren't rational actors, that connection isn't a conversion rate, that the best things usually happen when you're not tracking them in columns. Was this how he played first base, back when he used to be somebody? Maybe it was, and that’s why he isn’t anymore.

My friend Marcus quit the apps two years ago. Takes Chinese cermaics classes now, where he says he "throws pots," whatever that means. Mandarin lessons in case he decide to make the East into a career. Parkour club. He's terrible at all of it. His pots look like abandoned bird’s nests. His Mandarin sounds like he's speaking into a payphone receiver through a mouthful of marbles. But he's here for it, in the world, doing the work badly with other people who are also doing the work badly.

"I figure if I meet someone, we'll already have something to talk about," he says. "Like how much we both suck at Mandarin, if she happens to be another expat."

That's probably the answer, if there is one. Stop strategizing. Stop treating people like data points and connections like conversions. Don’t be afraid to make a fool of yourself doing something in public. Show up to the same places. Talk to people without an agenda. Build an oddball life someone would want to join instead of a perfect profile someone would want to swipe.

The guy at my old gym will keep his spreadsheet. Keep letting AI write his loveless letters. Keep running into other people doing the same thing, two bots a-courting through their human proxies. The woman with the notebook will start a new one, still searching for the raw⁴ material needed to write the (So 2000 and) Late American Novel. The napkin-eating customer service rep will keep explaining why the algorithm isn't broken while quietly consuming her paper hors d'oeuvres. And somewhere, maybe, two people will meet at a bus stop or a pottery wheel⁵ or an unhelpful Mandarin lesson.

It won't jive with Lean Six Sigma. It won't be scalable or exportable. But you know what? It might actually work.⁶

1. While you’re at it, check out all the cool non-Substack stuff I’ve written recently:

“Make the Most of Aaron Rodgers’ Last Run in Pittsburgh” in RealClear Pennsylvania and Pittsburgh Tribune-Review

“Zohran Mamdani Heralds a New Era of Democratic Politics” in UnHerd

“Make America Fit Again: The Case for a Civilian Fitness Corps” in Pirate Wires

2. We need another one of those almost as much as we need a second round of lockdowns.

3. “It’s okay by me,” a student once told me when I pressed them about whether their subpar work was acceptable.

4. “Rancid” might be more apt here.

5. Like in Ghost!

6. Your own harshest (inner) critic: “Probably not for you, though. But for somebody who isn’t you, sure. It might work wonders for them!”