I met my first boyfriend, Rafa, in an AOL chatroom when I was 12 years old in what I now consider an elaborate piece of performance art.
Most girls my age had already had “boyfriends” at that point—nothing physical but merely a boy who hung out in their vicinity and would come over for parent-supervised hangouts. But I was a late bloomer, and save for chasing my first-grade crush into the middle of the soccer field during a recess game, only to have him tell me to get the hell out of the way, I mostly stayed away from the boys in their Adidas pants and Gap sweatshirts.
I was a chubby only child, the only Jew from New York that didn’t go to sleepaway camp. My friends would return at the end of each summer with useful knowledge, like the meaning of “hook up” and how to give a handjob, while I played with dolls and occasionally took a break to ride my bike.
So when puberty reared its ugly head, I decided to pursue a relationship in the most nonthreatening way possible: on the Internet. My best friend at the time, Leah, and I would go into chatrooms to talk with strangers and take on different, mostly harmless personas. Sometimes we were a cool 20-something girl. Other times we posed as a slick teenage boy. But one day, in a chatroom, while once again pretending we were older than we were, we started chatting with Dragon42145.
Rafa was the fingers and face and body behind Dragon42145, and if this chat was a game of poker, then his vocabulary and phrasing were his tell. They gave him away as a kid just like us, taking on a more mature persona and testing the boundaries of the Internet to see what would happen. His friend Dan served as his online flirting copilot.
And thus began a double online relationship.
Each day after school, Leah and I would hop off the bus, grab a snack, and scurry down the thickly carpeted stairs into the basement of her house where we’d flip on her iMac and huddle around the stout, clear-and-teal monitor while it went through the lengthy process of booting up. This minute or so often felt interminable, while we racked our brains for bits of information about our days to share with the boys. When all systems were go, we’d sign into one of our AOL accounts, and as soon as the login was complete, our eyes would dart to the buddy list docked on the left side of the screen to see if Rafa or Dan were online. If they were, we’d wait. And if they weren’t, we’d also wait.
The Internet as a starting point for relationships has always been my reality.
Unlike in later years, where the politics of texting and online interactions would inspire hours of conjecture over cheap bottles of wine, Rafa and Dan were as dependable as golden retrievers and would always establish contact first. They seemed just as excited to talk to us as we were to talk to them.
Leah and I would take turns helming the keyboard, telling our Floridian friends about drama at school, talking shit about our other friends, and flirting in the way that only 12-year-olds can—calling each other “losers,” exchanging poorly cropped photos, and making up fake boys from school who had fake crushes on us. In a matter of weeks, we had boyfriends.
I’d eventually go home, across the street to my house, and that’s when Rafa and I would chat alone. We’d talk about more serious stuff, like our families—his struggles being raised by a single mom, what it was like for me growing up as an only child, and how we missed each other even though we’d never met. It was strange to feel such an intimate connection and feel so close to a person I’d never physically laid eyes on. All the people I was close with up to that point were people I’d known most of my life: my parents, one of my babysitters, a few of my friends. But here he was, a new person entering my orbit without actually being there.
After some time, it turned out that I was going on a family vacation to Miami, and I’d finally get to meet Rafa and Dan. Leah, for her part, was insanely jealous. I’d been tasked with remembering every single detail about them for our post-meeting debrief phone call. It seemed like the most important thing I’d ever have to do—the climactic moment in our ongoing performance as two cool chicks with equally cool boyfriends who just happened to live hundreds of miles away.
A couple of days into my trip, the boys came to visit our hotel. They pulled up in a small white sedan driven by Rafa’s mom and climbed out of the backseat. I stood on the curb in front with my mom, who insisted she come along, lest I be murdered by some strangers from the Internet.
And there we were. Four strangers nervously shifting our weight. I vigilantly avoided eye contact because I knew that if I took even a moment to look directly into Rafa’s eyes, I’d be struck with the harsh realization that the last few months were a waste of time. That we’d fooled ourselves into thinking we’d been carrying on a meaningful relationship, as opposed to the truth: that we were two stupid kids who didn’t have any idea what it meant to be in a relationship.
It occurred to me that all these months, when we thought we were being our true selves, we were actually just putting on new elaborate personas.
I studied them carefully, observing that Rafa had more acne than expected and Dan was more overweight than he appeared in photos. I was also acutely aware that they were probably making similar mental notes about me at the same time. I wanted to duck behind my mom like a child and hide.
Mom took us across the street to Cosi for smoothies where she and I sat across from the two boys in a table flush against the floor-to-ceiling glass windows, interview style. My mom, a therapist, filled the hopeless silence by posing questions to the boys like what they did for fun and their favorite subjects in school. And true to pubescent boy form, they replied in broken sentences—“soccer,” “math, I guess”—while making nervous eye contact now and then. I, for my part, became completely mute. With the same obstinance I used to win a fight with my mom, I would not allow for a word to pass my lips. I was judging their lackluster looks and Rafa’s shabby car and feared that the kids back home were watching a livestream (if such a thing existed back then) of this mortifying encounter while hurling snack packs at the screen. I morphed into the perfect mutant preteen monster. Poor mom. Poor Rafa.
We somehow managed to pass the time until Rafa’s mom came to retrieve them. Perhaps it was 45 minutes or maybe it was six hours. I did everything I could to forget I existed that day, which left little time to glance at a watch. While we had felt so bold and grown-up, so adult, so ready for love online, here we were on a mature playdate at best, our youth so readily apparent. It occurred to me that all these months, when we thought we were being our true selves, we were actually just putting on new elaborate personas. This time, we were playing young adults who were ready for relationships.
We parted ways with awkward hugs—ass out, pat on the back—and that was it. The spell was broken, reality set in, and we never spoke again.
Months later, my next relationship would also begin online. Every weekend in eighth grade, my friends and I hung out at the movie theater in town, during which time we saw every film that came out between September 2000 and June 2001. One movie night, I laid eyes on a tall, dark, and handsome stranger who looked about my age and whom I’d never seen before. A sleuth from a young age, I decided to investigate. I gave a full description of him to my friend who went to a neighboring school, and she deduced that, without question, it had to be this guy named Sean. So she gave me his screenname and I sent him a message. Easy, peasy.
Well it turned out that Sean hadn’t been at the movies that night, but neither of us thought it was weird at all that I’d reached out to him completely out of nowhere, because this was becoming a normal part of our lives: strange names flashing across our screens at random, with no lengthy explanation necessary. We began IMing incessantly until we finally agreed to meet one summer day at 2pm to see a showing of Legally Blonde, and after he briefly felt me up, I had my first real kiss. When I replay the moment in my mind, the opening chords of the Beach Boys’ “Don’t Worry Baby” swell, and we’re in the center of a heart-shaped frame like the ones on stadium kiss-cams.
The spell was broken, reality set in, and we never spoke again.
Within a month, Sean and I were over. He broke up with me for a girl he met at his Greek Orthodox Church, and I was obviously devastated. Sean, a champion middle-school wrestler, was out of my league, by kid standards. But the Internet made this unlikely union possible. The best part was that I was 100 percent myself. I learned from the Rafa disaster that playing the part of someone else would get you nowhere. In the end, I still got dumped. But at least it was me, and not some version of me, that got the boot.
It’s natural to long for “the good old days,” before dating apps invaded our lives and made the quest for real human connection and emotion seem like a thing that would forever evade us. My parents and grandparents can remember a time before this way of life. But truth be told, the good old days never existed for me. The Internet as a starting point for relationships has always been my reality.
I try to think about how irrevocably different my early adolescence would have been without this medium. How many more years would it have been until I found a boyfriend? Would I have turned out to be the second coming of the 40-year-old virgin?
Despite the ways we blame technology and social media for the downfall of human communication and the breakdown of meaningful relationships, I don’t think we can unilaterally say it’s bad. It helped me meet a boy in another corner of the country and also one in the next town over. It helped me realize that I was funny and that I could be an object of desire.
And while most tales of Internet romance are far less innocuous, it can be a place for genuine connection. It can be the place where you find love, and for me, the place where I found my nerve.
Illustration by Max Fleishman