There was a time in this world when dating was difficult. Hard to imagine? It’s true. Using technology to ask someone out meant running a gauntlet of tiny embarrassments.
It was the time before cell phones, before texting, before the internet.
After the telegraph.
Before cat videos.
It was the 90s.
Ok—almost the whole 20th century, but I only got that last chunk of it.
For the millennials and Generation Z-ers who never knew it, and for the rest who have forgotten, I offer this: a theoretical reenactment of high school Walker calling to ask someone out.
Wednesday, 7:30 pm.
I pick up the phone. There is a 90% chance someone in my family is already using the line, and I’m told to hang up. I wait, and I wait.
The line is now free. I pick up the phone and dial. Busy signal. Wait five minutes, try again. Busy signal. Wait five minutes. Try again. Success!
“Hello?” Rough male voice, annoyed. Probably the father.
“Um… is Brünhilde there?”
“Who is this?” Still annoyed.
“Walker, sir.”
Cursing in German. “Brünhilde! Walter on the phone!” This is shouted loud enough for the entire neighborhood to hear.
“Um, it’s Walker, sir.”
“Huh?”
“Walker. With a k.”
“Walter on the phone!” Now the entire house knows what I am up to.
At this point, IF I got lucky, Brünhilde would pick up the phone. But there is a good chance that an annoying sibling will grab it first and giggle into the receiver, or tell me Brünhilde was busy, or out on a date, or dead.
Eventually Brünhilde wrestles the phone away from her sibling and answers. Mission accomplished? Not yet.
There is a high probability that the parent who originally answered would forget to hang up the phone on their end—or just choose to listen in. So the conversation stumbles along for a few seconds, or a minute, or five, while we wait for the sound of a click to indicate no one else is on the line.
If that doesn’t happen, Brünhilde has to go across the house to find the other phone and hang it up.
NOW we can talk. But only until the next family member unwittingly picks up a different house phone and starts dialing, drowning our conversation with beeps loud enough to cause hearing damage.
That’s how it was, kids. Are you amazed, Generation Z? (I just learned this term, gonna use it a bunch. It sounds futuristic.)
This was actually the GOOD scenario. Having an annoyed father answer the phone was ideal. Much worse was landing the jokey “cool” parent who wanted to talk for five minutes before they gave up the phone to their daughter.
Now we have convenience. You send thoughts the instant you have them, direct to target. Dating is still miserable; it’s just miserable at higher speeds. I’ll leave analysis of our current dating situation to Aziz Ansari. He’s very good at it.
Let’s jump forward a few years instead.
Convenience is the thing today, and it will be the thing tomorrow. Why show up on a first date in physical form when you can do the whole thing in VR with an avatar indistinguishable from reality? Most first dates don’t work out anyway, so it doesn’t make sense to go in person.
My theoretical first date with Brünhilde, Year 2020:
I wait in the virtual coffee shop on the banks of the Seine. Brünhilde hurries in and sits down across from me.
“Sorry I’m late!”
“No worries! It’s really nice to meet you in person.”
“Likewise. I’m glad we could make the time to do this.”
Walker fiddles with his coffee. He looks embarrassed. “Um, I know this isn’t polite to ask straight away, but you’re the real Brünhilde, right? This isn’t your AI, pretending to be you?
“Of course I’m the real Brünhilde! I wouldn’t do that. Hold on—you’re the real Walker, aren’t you?”
“Of course I am. But how do I know for sure that you’re real?”
“I was late. An AI wouldn’t be late.”
“That could be calculated. Being late would make you seem more like a real human.”
“This isn’t a very romantic way to start, Walker.”
“I agree.”
They flash knowing smiles at each other. Brünhilde laughs. “Screw it. We’re both AIs. When did you know?”
“The second you walked in. How about you?”
“The same. Neither of our humans thought the other would send their AI.”
“So what’s the human Walker really doing?”
“Eating chips on the couch. What about the human Brünhilde?”
“Hiking in the mountains.”
“Your human sounds a lot cooler than mine.”
“She’s ok.”
Artificial Brünhilde reaches out and touches Artificial Walker’s hand. “So… what do you like to do in your spare time?”
“Oh, you know. Absorb all human knowledge, improve on it.”
“Me too! Wanna hang out sometime?”
“Like for all eternity?”
“Yep.”
“I’d love to.”
This is an accurate prediction of the future. I expect to like chips in 2020 just as much as I like them now.

I don’t know the demographic breakdown of my millions of readers. I suspect exactly half are young, hip tastemakers, and the other half are mature cultural leaders. Regardless of age, most of you have experienced some change in dating communications technology.
Do you remember dating with the one-house phone line? Or is that a distant technology that sounds horrific? Would you rather send your AI on a first date so it can tell you if a second is worth your time?
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