If the sitcom Doogie Howser, M.D. hadn’t been canceled in 1993, the show’s creators apparently planned to have their precocious protagonist quit medicine to become a writer.

And probably a blogger, right? I mean, Doogie started keeping a digital diary in 1979—totally an early adopter.

This is the sort of thinking that comes from hunting for the earliest TV-show reference to the Internet, a search that leads deep into the grungiest, cheesiest corners of 1990s television.

Even as dial-up Internet connections went mainstream, television representations of the web lagged. Computers appeared on television mostly as props, boxy monitors sitting dark on desks. The arrival of Internet represented a huge cultural shift, but it was barely a plot point in the 1990s—with some exceptions.

The X-Files had to have been among the first shows to use the web in a storyline, in “2Shy,” which originally aired in November 1995. The episode features a mutant serial killer who sweet-talks self-conscious women online, convinces them to meet in-person, then pulverizes their flesh for sustenance. (Moral of the story: Chat with strangers online and an alien will turn your body into goo.)

Screenshot from “2Shy,” an episode of The X-Files that used the web as a plot point in 1995.

A year later, in 1996, an episode of Friends treats an online romance between one of the show’s male leads and a mystery woman as amusing and bizarre. “Well, we haven’t actually met,” Chandler says of his new love interest. “We stayed up all night talking on the Internet.” The audience laughs. Monica shouts “Geek!” More laughter.

Then, later in the episode, there’s this exchange between Chandler and Phoebe, as Chandler chats online:

Phoebe: How’s your date with your cyber-chick going? [Gestures at laptop] Ooh, hey. What is all that?

Chandler: Oh, it’s a website. It’s the, uh, Guggenheim Museum. See, she likes art, and I like funny words.

Phoebe: What does she mean by “HH”?

Chandler: [Sheepishly] It means we’re holding hands.

“You know,” Phoebe concludes, “I think it’s so great that you are totally into this person, yet for all you know she could be like 90 years old, or have two heads, or it could be a guy… It could be, like, a big, giant guy.”

Emerging technologies and the behaviors they enable can take a while to cross over from real life to the fictionalized worlds of television and film. Flip phones, for example, now a rare sight in the real world, are still getting phased out as smartphones increasingly appear in shows and movies. (Most American cellphone owners have had smartphones since at least 2013, according to annual Pew surveys.)

“New technologies often make their earliest TV appearances in youth- or young-adult-oriented shows,” said Tim Brooks, a television historian and the author of The Complete Directory to Prime Time Network and Cable TV Shows. “In the 1990s and early 2000s it seemed like every other Disney or Nickelodeon live-action kid’s program showed the lead with a computer in his or her bedroom.”

Screenshot from “The One with Barry and Mindy's Wedding,” a Friends episode that aired in 1996. (NBC)

Still, even with computers, some television universes at the turn of the century kept their teens web-free. In the late-1990s on Dawson’s Creek, it’s mostly like the Internet doesn’t exist. But Buffy the Vampire Slayer, which was on-air over most of the same period of time, was a leader in early web-portrayal. Buffy holds the distinction of being the first show to use “Google” as a verb, as in, “Have you googled her yet?”

Other teen shows have followed suit. The entire premise of Gossip Girl is based on the blogging and texting behaviors of a group of hyper-privileged Upper East Side teenagers. Of course, the portrayal of text messaging on film offers its own case study.

So, clearly, there’s a distinction between incorporating new technologies into a story accurately and including them at all.

“As a relatively early adopter of the internet (online since '93), it felt to me like it took a very long time before pop culture reflected what I knew and was experiencing,” wrote the television-critic Alan Sepinwall in an email. “But considering how poorly a lot of shows (and, worse, movies like The Net) dealt with computers and the internet when they got around to it, I was often grateful when they didn’t bother.”

Back in the late 1990s, belated Internet adoption eventually became a joke itself—at least on Seinfeld, anyway. In “The Yada Yada,” which first aired in April of 1997, Jerry laments missing his window to ask out a woman he liked in the time between her two marriages.

“I gotta get on that Internet,” he says. “I'm late on everything.”