In 2000, I taught myself basic HTML coding so I could design a private chatroom to use with Tom, a fortysomething-year-old man who liked skiing and listened to the Fine Young Cannibals. I built us a room with a tiled background image of purple velvet curtains and a quiet Fiona Apple loop playing in the background, and gave him the URL so only he and I could access it. I told him I was in my late twenties, but I was 12.
I spent a lot of my adolescence talking to older men on the internet. It started off as an activity at sleepovers. My girlfriends and I would flit through AOL chatrooms, meeting guys (A/S/L: 19/f/Florida; we thought Florida was an exotic place to be from). Our early games were about how far we could push our weirdness before the guy would get fed up and block us: “Do you have oranges in your house, baby? Would you make some OJ for me and feed it through the floppy disk drive? That would be so hot.”
Over time, I began exploring on my own and talking one on one with guys, where things got more serious. I decided identifying myself as a teenager was not convincing (everyone on the internet said they were a teenager), so I said I was 27. And that was how I knew — or at least, I assumed — that these were not guys who were interested in me because I was underage. I worked hard at plausibility; I created fictional coworkers cobbled together from my teachers and classmates and did internet research and consulted my brother’s Dilbert books about what it would be like to work in an office. I complained about working in a cubicle instead of an office with a door, and they commiserated.
In those days it was rare to have a webcam; you could believably say you didn’t have a photo of yourself online and had no way of putting one there. Writing all of this makes me feel as old as a desiccated bog mummy, but it’s important to mention because the internet used to be completely different. Back then, there were no search results for me, no social media profiles. It was exciting and novel to find someone else on the internet; only 5% of the world’s population was online, rather than 57% now.
The men on the internet weren’t the ones that I needed to worry about. It was the men I met in real life.
If my life were a made-for-TV movie, I would have met up with one of these guys at a motel, where he would have kidnapped me, and it would have been up to my mother and my best friend to put together the clues to find me and bring the dude to justice. None of this happened. Instead, the relationships I developed with men online gave me a fix of being treated like the grown-up I longed to be, which made being among my peers in school more bearable. On September 11, 2001, it was a digital thirtysomething British bank manager who offered me support and comfort. These men were not predators. I took advantage of the utter anonymity of the internet and my precocious self-expression to deceive them. And in retrospect, I feel guilty about lying about my age so that I could experience what it felt like to be taken seriously.
It is easier and safer to conceptualize children on the internet as vulnerable, potential victims. Indeed, when I hear about a colleague’s 10-year-old niece who is a YouTube star, I want to slither into a storm drain and die. I’m not immune to the panic of imagining what kids might do with the internet, a portal of connectivity, power, and risk, and one that no one person can understand all of the contours of.
So where do I file my own experiences, which never felt like exploitation or abuse? I worry that when I talk about my early sexual life on the internet, I will be subjected to pity or scrutiny: Where were the parents? (Always around.) Was I working through childhood abuse or trauma? (None in my history to work through.) Either way, the men on the internet weren’t the ones that I needed to worry about. It was the men I met in real life.
I was a deliberately provocative, sexually precocious teenager, and was thoroughly bored by boys my age. In ninth grade I devoured Vladimir Nabokov’s Lolita, envying Dolores Haze, conspicuously reading the book on the subway to see what kind of attention that might draw. Once a month, my girlfriends and I met up at an all-ages Britpop and ’80s dance night, and the excitement of a guy smiling at me across the room fueled me for the rest of the month.
But I shied away from anything physical; I wasn’t ready. Plus, there was a kind of energy to the men who orbited me at that age: the men who wanted to talk to me about bands and movies, the men who told me that I was wasting my time with high school boys who wouldn’t understand me. They extolled me for my maturity, but unlike the guys I talked to online, they wanted me for my youth. Unlike the men online, they moved forward knowing full well how old I really was.
These men wanted me to know they saw that I was wise beyond my years, that they could see that I was different. And I was all too keen to prove my difference, how special I was: I wanted to talk to them about my anti-war efforts, my favorite Dischord albums, an article I published in Adbusters magazine. But when they drew close to me to touch my arm or my hair, I recoiled. The reaction was visceral and unconscious. I knew I did not want to be with the men who wanted to be with me at my age. I wanted attention, but I also knew that the guys who would give it to me were probably creeps.
I waited until my 18th birthday to pursue older men in earnest, because I assumed that by the time I was technically a legal adult, the power imbalance would be completely equal from there on out. I started dating a 30-year-old musician I met on Myspace (again, writing this sentence makes me feel extremely old!). He told me that I was wise and mature beyond my years. He said he’d never dated anyone as young as me, but he felt connected to me in a way he couldn’t ignore. Hook, line, and sinker. We kept in touch through my first semester at college and fell in love over emails and phone calls. I lied to my parents about where I was going over fall break, and I spent a long weekend at his apartment.
After six months of unsuccessfully sending nonverbal signals that I was ready to have sex, I called him up one day and asked him to take my virginity. He said he didn’t want to, that I was too innocent, and that he wouldn’t want to “ruin” me by doing that. I told him I thought my virginity was nominal and no big deal (I said something like “I wasn’t too innocent to suck your dick”) and that I really wanted the first time out of the way so I could enjoy my sex life. He agreed.
One night, he put on the movie Beautiful Girls, a movie where the main character, a 29-year-old man, returns to his hometown for a high school reunion and falls in love with his 14-year-old neighbor, played by Natalie Portman. I felt queasy as the credits rolled. Is this what he wanted me to be? Some kind of pliable, underage “cool girl” who could play second fiddle to his A-plot? Did he find me being off-limits more desirable than me being available and wanting? The movie ended and he pulled me closer to him. I had to stop him to insist that he use a condom (“Why? You’re a virgin, you definitely don’t have anything I could catch”). He dumped me two weeks later and his Myspace photos began featuring a new, vivacious 17-year-old girl.
Youth is a sought-after quality, particularly in women. This preference is reflected in our porn, our entertainment, our job market. A 2018 study of a month’s worth of data from one online dating platform found that among people seeking opposite-sex dates, the age of a woman’s peak desirability (based on the number of messages received from other users) is 18 — the first year she is legally allowed to use the site. The peak age for men is 50. Furthermore, a woman’s perceived desirability drops if she attains a postgraduate degree, even when controlling for age. Many evolutionary psychologists claim the reason for pursuing youth is biological and based on the age of peak fertility (which somehow doesn’t apply to men, who experience a drop off in fertility starting at around 40). But the preference for less educated women, with other things being equal, points to a different dynamic.
Bound up in the way female youth is packaged are ideas of innocence and inexperience, a deferential guilelessness. The less we know, the better. The state of not knowing is sexually desirable in and of itself, which begs the question: Why? Underage female celebrities are often subject to an internet countdown clock, which ticks away the minutes and hours until they are legally of age to consent to sex. This is the point at which it is no longer technically statutory rape to sleep with them, but there is no biological developmental difference between 17 years and 364 days old and 18. American culture is fascinated by the barely legal status of young women and the dewy wrongness the title confers.
American culture is fascinated by the barely legal status of young women and the dewy wrongness the title confers.
Of course I am painting with a broad brush. Not all intergenerational relationships are exploitative; they can be loving and mutually supportive. There are also many couplings between older women and much younger men — which have just as much of a chance of being predatory or inequitable as any other kind of relationship — but culturally, we overlook this possibility because women aren’t perceived to be threatening. Abuse in same-gender relationships can also be overlooked in the same way: Without the male-female gender dynamic, queer relationship imbalances aren’t as readily visible. But in the same way, many intergenerational queer relationships can be strong, equitable, and loving. All that said, it’s hard to deny that both data and anecdotal evidence point to a troubling pattern of older men who seek out very young and vulnerable women — one that’s reinforced by some of the most powerful and visible people in our society.
Many high-profile men swim in the waters of barely legal romance. Jerry Seinfeld dated an 18-year-old when he was 39. Woody Allen’s artistic obsession with relationships between middle-aged men and very young women has clear roots in his own life. Leonardo DiCaprio, now 44, hasn’t publicly dated a woman older than 25. Most recently, Moby made headlines for claiming in his memoir that he had a relationship at age 33 with a then-18-year-old Natalie Portman — and when she pushed back in an interview, describing her memory of him as “an older man being creepy with me when I just had graduated high school,” he doubled down before finally apologizing. “I accept that given the dynamic of our almost 14 year age difference I absolutely should’ve acted more responsibly and respectfully when Natalie and I first met,” he wrote on Instagram.
But of course this phenomenon isn’t exclusive to celebrities. When I ask around, most of my women friends have their own version of Leo or Moby, older men who pursued them at the cusp of their adulthood. These men praised their rebelliousness and presented themselves as the alternative to a teenage girl’s mundane life, as if there were no better way to stick it to the man than…sticking it to the man. These men paid attention to my friends because they were mature, “not like the other girls.” They paid attention to me, too.
I reread Lolita during my senior year of college. This time I saw Humbert’s mewling self-pity, his delusion, and his malice. There was something in the text that I had read the first time, but not understood. I had to date my own unreliable narrator to be able to understand the book’s subtext.
Because of my desire to be taken seriously, I was a mark for older men to take advantage of — not just my first boyfriend, but many before and several since. I don’t blame myself for my curiosity or interest, and at the same time, I believe that the way I positioned myself socially enabled encounters with older men. The line was clear when I was underage, but once I crossed that threshold, things got murkier.
It’s not illegal, so why does it feel so gross? Maybe because it’s hard to imagine what a man in his thirties has to say to a teenage girl. Why is he interested in her?
I don’t blame myself at that age for being interested in older men who were more worldly than me, who acted more self-assured than boys my age, who didn’t live with their parents or in a dorm room, who confirmed the image of me that I wanted to cultivate. I do blame my first boyfriend and the guys like him, men who had a hard time finding women their own age to date because those women saw through their bullshit. Men who returned to a certain age or stage of development to recreate or correct an experience over and over, using teenage girls as collateral. I still don’t know how to categorize the experiences I had — ones that I consented to, even pursued, ones that I thought I was ready for at the time, ones which now turn my stomach. I’m still trying to reckon with the idea that talking to men three times my age as a preteen felt safer than dating as a technically legal adult.
A man in his thirties or forties pointing to his sexual relationship with a teenage girl as technically legal is a Pyrrhic victory. Why is that something to boast about or be proud of? How low could the bar possibly be? Just because someone is not committing a felony does not mean their behavior is appropriate. Youth is a kind of power because of the way we value it, but it’s nothing compared to the compounding effects of experience, age, financial autonomy, social standing, and gender privilege. The idea of someone being “old enough to know better” relies on the more powerful party to be responsible, with very few consequences if they aren’t. We have seen what happens when it’s up to the powerful to self-govern and self-regulate.
I’m still trying to reckon with the idea that talking to men three times my age as a preteen felt safer than dating as a technically legal adult.
Of course people should comport themselves ethically, of course people should be able to not act on their impulses, and of course people develop at different times (there are some teenagers whom I would trust to run this country, and there are plenty of adults whom I wouldn’t trust to water my plants). That said, our brains do not click into final draft mode at 18, with capacities like judgment, reasoning, and risk-taking regulations still solidifying well into our mid-twenties.
I’m not advocating for raising the age of consent to 25. It’s not about that. It’s about interrogating the role of power in intergenerational relationships that start when one person is just out of statutory range.
We’re more comfortable believing that these men are anomalies. They must be people with no friends, seething monsters prowling in alleyways, we think. But their soft-coercion tactics wouldn’t work if that were the case. These are guys with jobs, hobbies, social lives, cachet, influence, power. I probably know more of them than I think I do. You probably do too. I wonder what these guys I knew thought was going on, if they believed everything they told me when I was a teenager. I wonder if they still think they are good guys.
Did you have one of these guys, growing up? An older man who made you feel special, who kept circling back to you, who technically didn’t break any of the rules and kept reminding you of that fact? I eroticized that danger when I was younger, and now, when I see older men trying to chat up women who look way too young, my throat catches. I have since learned to trust the churning ice machine in the pit of my stomach, the one that pulls me away from people who feel like bad news. I didn’t trust my gut as much when I was younger, so I deferred to those around me, those with more experience. That was why my naivete and inexperience were so hot to the older men who dated barely legal me. I let them lead, assuming they would have my best interests in mind.
I am now the age my first boyfriend was when I was 18. I am trying to imagine my now-30-year-old body being swiped into a freshman dorm with a white keycard, ushered past chipped wood doors with cheery foam nameplates, swinging one open to face a double room — a room with standard-issue particle board furniture, a cloth tapestry on one wall, a bong on the windowsill. I think about greeting a roommate who murmurs a wary hello and slinks out the door to the common area. I imagine taking off my shoes on mottled carpeting and sliding into one of two twin XL beds next to a teenager, rubbing his back and asking him quietly to stop reading for class so he can go down on me. The thought is poisonous.
One night a few months after my 21st birthday, an older man in a suit approached me and my friends at a bar and asked if he could take me out to dinner. I smiled through my discomfort and said, “No, thank you.” He opened his mouth to rebut me, but in an instant his friend was at his side. The friend put a hand on his shoulder and said, “c’mon man, she’s too young,” and pulled him away.
It was a brief interaction a decade ago, but I remember it because I had never seen another guy intervene like that before, and I haven’t experienced it since. Maybe we should move away from “old enough to know better” and move toward “old enough to do better.” What older guys know will protect no one, but what they do — or don’t do — might. ●