The internet was a pretty magical place to find yourself in the late ’90s and early ’00s. So many people did so many weird and creative things as they explored this new medium, trying to figure out what it was, trying to determine what it would be. It was like a speakeasy, or a door under the stairs that led to an entirely other world. For many people it was scary, an unknown thing they were happy to not understand. But for a certain set of people, it was a new home.

Suddenly our social circles were widening in ways we never could have anticipated. People shared our weird interests! All over the globe! And now we could connect to those people, more easily and meaningfully than we likely ever could have in the real world. We established relationships; we made new friends; we formed emotional attachments through our computers; very quickly, the internet became an important part of our lives.

We wanted to share it with other people. We evangelized it and tried to explain why it was so great, but for many people it just didn’t click. They didn’t need a web site. They weren’t sure what they would write about once they signed up for a Tripod or Xanga site. We couldn’t wait to go deeper in to this world, but they couldn’t think of a reason to set foot in it.

“People psyched about the internet” was a very small segment of the population, and it stayed that way for a long time. Our ability to search for people with shared interests (it wasn’t known as Googling yet) had the weird side effect of making stark how many people were missing from this new conversation. What about the people we already knew, but who for whatever reason weren’t as excited about this new medium as we were? If the internet was so good at helping us meet new people, maybe we could also use it to reconnect with old people?

What had happened to the people we already knew and lost touch with? Friends from elementary school who’d moved away the summer before sixth grade, old neighbors, family friends, first loves. Maybe even bullies and enemies and exes. Especially exes. Where were they? What were they doing now? Could we discover how their lives had turned out after they’d disappeared from view? Could the internet please give us proof that the people we cared about were happy, and the people we hated were miserable?

Nope! We quickly learned that the internet was actually terrible for connecting us with people from our old lives, our lives offline. [...]