In 2001, I was 16, sitting at the computer in the family room when my best friend, MarlaM12, found me on AIM. I hid a smirk with a frown so my mom wouldn’t wonder what I was up to — at that moment, trying not to be turned on. MarlaM12 was instant-messaging me a guide to phone sex: “Practice saying things like, ‘You make me so hot’ … the basics can be extraordinarily arousing when they’re said out of context or in a different situation.”

For women like me who were teens and preteens in the late 1990s and early 2000s, that “different situation” was AIM (AOL Instant Messenger). Chatting online was our “out of context,” because interacting fact-to-face meant awkward, eyes-on-the-floor self-consciousness that defined middle or high school. Online was better. You could “…” through an awkward silence; draft messages in consultation with your BFF; study your chipped nail polish instead of looking straight into the eyes of the person you hoped “like-liked” you. You could pretend to be a grown-up, because you were at a computer and not surrounded by lockers and classrooms. 

AIM was always a way to talk. But when you’re an adolescent, talking is a way to flirt and flirting is a way to figure out who you are. AIM created “a safe space,” genderqueer writer and performer RE Katz tells me. “I could reproduce normative femininity … mostly faking, some experimenting, performance.” That performance — complete with the costume of a font and the character of a username — was an attempt at being clever or sexy, at crafting a self. Katz credits AIM as helping shape their own gender expression today. Maybe that’s why news that AIM will be discontinued on Dec. 15 has yielded such an emotional response from millennials who grew up while IMing their friends about their homework or their crushes.

The technology was new, but it wasn’t that different from what adolescents have been doing for ages. “Teens used the service to flirt through text, engaging in a form of written flirtation that looked a lot more like letter-writing practices decades before,” says Danah Boyd, author of “It’s Complicated: The Social Lives of Networked Teens.” That written flirtation allowed young women to construct their identities as carefully as their away messages. Were you fun? Dirty? Bold? Brainy? Did you identify more closely with the lyrics of Dashboard Confessional or the writings of F. Scott Fitzgerald?

On AIM, you didn’t have to choose. You could sign off with “ciao” one day, “peace out” the next. “Having the Internet as a catalyst for learning how to interact with your peers was invaluable, and it was also pretty innocent,” says Caroline Moss, a co-author of the upcoming “Hey Ladies!: The Story of 8 Best Friends, 1 Year, and Way, Way Too Many Emails” and the Twitter account @YourAwayMessage. “I think it helped young women feel like they could come into their own in a lot of ways,” Moss says.

For me growing up, AIM was a release. In class, I was the person with the right answer — or the person constantly competing with the other smart kid who said it first. But online, my friends and I who fashioned ourselves as budding intellectuals who didn’t need to always talk like characters in a Woody Allen movie. We planned Halloween costumes and epic homecoming sleepovers. We talked about our eating disorders with a candor unavailable to us at the lunch table. When I messaged boys I liked, I learned to have conversations where there was no pressure to arrive at a right answer. Chatting online, rather, the goal was just to banter. I got to see that bandying ideas around for hours could be a path to intimacy.

It was in those unstructured conversations that I could be typing so fast my guard came down. “It was pleasurable to meet new people and learn that you were ‘attractive’ somehow,” Katz recalls. “Do you remember what it felt like for a relative stranger to be like: ‘I see you’?”

Yes, I do remember. It felt like cartwheeling down a moving walkway, going with the flow and yet still sticking the landing. But developing a sexual identity was as difficult as choosing a screen name. Katz told me AIM “was a way we learned to enact pleasure or demonstrate that we were feeling pleasure, even and especially if we weren’t.”

At the same time we were using AIM, my best friends and I were also listening to NSync. We were fans, but we made fun of one song: “Digital Get Down.” We thought it was “awkward” how NSync made a song about asking some girl to touch herself on a webcam. Today, such requests seem tame compared to the sort of sexual coercion marking Harvey Weinstein and other sexual harassers. Exploiting yourself on the quest for attention was one risk with AIM. A friend of mine reminded me of the way, at sleepovers, we used to go into chat rooms, pretend to be in our 20s, and try to get men to “cyber,” the AIM version of phone sex. Another friend recalled the time a boy we knew from school told us to get drunk while we chatted.

My friends and I played sexy on AIM because, in real life, we were bound to the rules of our parents, Catholicism, and the code that tells “smart kids” that sexual experimentation is for screw-ups. We lied and pretended we got drunk, laughing at our crafty misspellings. As Boyd notes, “AIM came on the scene at the height of the first large moral panic around online sexual predators and so the media and many parents panicked about the service, deeply frustrating teens.” We heard stories of women and girls who got raped or murdered by guys they met in chat rooms, lechery that now seems like prelude to the Craigslist murders and Tinder rapes. Our response to these horror stories was to be judgmental. Weren’t we smarter than those people? Probably not. We were lucky.

Still, the risks of AIM were some of its greatest rewards, especially for teenage girls. “You had middle school students getting brave,” Moss says, “asking one another questions about sex, experimenting with language, acting in ways they knew to be inappropriate for school.” For young women who were told that their pleasure was inappropriate, the opportunity to develop a sexual identity online was invaluable. AIM helped us become everything our screen names promised we could be: clever, corny, simultaneously over-the-top and understated expressions of ourselves.

Today, we might not need to be secretive about learning how to have phone sex. There seem to be no limits to the sexual explicitness we consume in music and TV and film. But some things are still hard to do, and maybe they’ll only get harder the more digital intermediaries pop up, giving us alternatives to face-to-face intimacy.

A few months ago, a friend from graduate school asked if I wanted to Gchat (which has since folded into Google Hangouts). I found myself asking questions that reminded me of being a teenager, the sort of things you could only ask in the middle of the night, and he always responded candidly. I began to feel like I really knew him. It had been years since I got to know a relative stranger that well. Recently, I have wondered what would happen if I were to run into this friend in person. Would I be bold enough to look him in the eyes and say: I like you?