Love & Sex

True Stories: The Twenty-One-Year Old and Me

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On the perks and perils of dating younger men.

When you sleep with someone from work, it's surprising to see them at work the next day. They never vaporize in a bad toaster-oven accident like you hope. The coworker I slept with is a college student eleven years my junior, and he brags the next day at the office about an even older woman he has been seeing for months. Though news of this older woman has been trickling through the office gossip chain for some time, I still find it disturbing.

I pull him aside. They are "not really dating," he admits, which is worse, because now I imagine that their sex is amazing enough to power California for a month. I figure they'll hit it until she moves to Vegas, where all the chosen cougars go.

This is how it is when I meet younger men. It's never this romance novel where I'm the first older woman, we break boundaries, and then there's some tawdry scene where we're caught zesting lemons together. It's more like the perv classic Lolita — that moment when Humbert Humbert realizes his corruption of Lolita is a sham, that she's been having threesomes at sleepaway camp for years.

My Lolito has been pretty busy. The other woman is about twice his age. Cougar One, Original Cougar, as I call her, has a more impressive degree than me and a far more impressive job. This other woman is a good thing, friends point out, because it means he's been taught already. I always wonder about this. Taught what? And what twenty-one-year old is humble and willing to learn?

Yet there must be real older-woman teachers out there, because I keep hearing about them, and not just when Susan Sarandon craps out another movie. Sexually confident women. Cosmopolitan women. I envision a whole trade fair of nipple clamps under the bed, coordinated with cream wool boucle suits. They eat at French restaurants with amuse bouches. I've decided amuse bouches are sexy. I've decided people who eat amuse bouches are sexy. This older woman he's dating must be one of them. A mythical creature-teacher. An unapologetic amuse boucher.

I would like to be one of these women. Like Bianca Jagger. Caftans look like ass on the rest of America, but I pull them off. I spend afternoons eating caviar out of the pool boy's bellybutton. I call myself "dirty old woman" the way men are called dirty old man. "Dirty old" just means you're perverted and aged. I can respect that. "Cougar" means you sit around in cheetah-print robes and eat a lot of Activia.

Most twenty-eight-year-old women would run away when they hear college freshman. I should have too. But I was strangely curious.

I have always been physically attracted to much younger men, but I never dated one until about six years ago. Our eyes met at a Bushwick warehouse party, and he came up and started dancing with me. This has happened maybe three times in my life, and every time I feel like a slightly cross-eyed Jennifer Aniston in a sweater shrug until they approach. He was really attractive, like a young Joaquin Phoenix. Initially he lied about his age and told me he was twenty-three, instead of twenty and a college freshman. Most twenty-eight-year-old women would run away when they hear college freshman. I should have too. But I was strangely curious. Would we make out in his dorm? What does his dorm look like? Would we eat microwavable Kraft products? Would I get caught buying booze for him? Was it worth it because he looked like a young Joaquin Phoenix?

He had many tales of debauchery. I find tales of debauchery very exciting, like I have participated in them just by hearing them from someone else. It's a wimpy way out for those of us who didn't smoke a cigarette until college. Part of me wondered what he would have left to look forward to his sophomore year.

The college freshman took me to see his dorm room, and only because I begged. ("You really want to see it?" he asked, confused. "Why?"). I don't know what I was expecting to find in there. Maybe I thought I could be elevated to a higher state by the mere sight of a Dave Matthews ticket stub. It was like every other college dorm: outrageously well-located, but ugly, from the standard-issue loft beds to the hospital-style lighting.

Still sometimes the thrill of an idea can be thrill enough. I imagined racing out of work, tossing off a "Gotta meet my man, you know, at his dorm" and watching my coworkers keel over in jealousy or barf up their bagels. Yeah, so it might not have been exactly like Diane Lane dating the hot younger French guy in Unfaithful. I didn't have a neutral-hued Westchester home and a neutral-hued family to run away from — just a total lack of dates with guys my own age. So this would have to do, as my own more ridiculous version. But looking around the college freshman's room that night, I didn't see my failure to score six-figure professionals, to get on the marriage plan with the promise of sectional sofas gleaming in the distance. I saw "bucking the system." By avoiding it entirely.

I didn't regard it as regressing. It's more like I didn't understand why certain paths are closed off to you when you're older, why there's one long road to domestic bliss for you to take and you're a failure if you don't jump onto that track by a certain age. If I was physically attracted to men who are supposedly too young for me, why couldn't I date them? Especially because the older I got, the more I learned that age hardly dictates maturity. With this solid reasoning, I went forth.

Our romance lasted two dates before he dumped me. But you know what? Sometimes it's not about longevity. It's about planting the seed, man. Planting the seed to something bigger and more beautiful than you ever imagined. Making a tree, my friend. The college freshman was a taste, and now I needed to dive in Scarface style.

After that, I became one of those sickos who hang around dog parks to pet dogs that aren't their own. Every time I wandered past college dorms or skate parks, I gave it the 45-rpm slowdown, admiring the scenery. I was like that old skeevy guy who hangs out at the mall to check out high-school chicks, sucking down a Sbarro Sprite for four hours.

As I get older, the friends who indulge me become fewer. I don't know when everyone falls through the hidden trap door, becomes an adult, and magically knows how to refinance their home. At thirty-four, I don't look, sound, or think that different from me at twenty-three. Neither, I reason, would the men I date. Still there's an unwritten rule that women between twenty-five and forty are supposed to like Don Draper. Dudes have got to have a lot of body hair, and you're supposed to spend like the next thirty years combing through it looking for a pot of gold or a sharable 401k plan. You have to hit fifty before dating someone half your age is considered cool, something Diane Keaton would strip off the old turtleneck for.

Of course, the number of young men I check out dwarfs the number I actually date. It is a whole five years and two jobs after the college freshman when I meet the twenty-one-year-old coworker. He sits a cubicle behind me, a part-time data-entry assistant working his way through college. He reminds me of every attractive guy in college I never got to date. The one who's nice enough to pass you the joint but then disappears off into the night to have sex with the annoying girl with the phenomenal knockers.

He kisses me on the cheek and utters the words, "It's been real," like we are in a '80s movie drinking cherry Slurpees.

He seems so much smarter and less spoiled than boys I knew in college, working to support himself while he plays in two bands and goes to school. I am impressed by his knowledge of Middle Eastern politics. We talk about Stewart Copeland versus Sting, girls in the office who annoy us, and my dream where I give birth to a parrot. I attend performances of his jam band, even though watching a jam band ranks up there with sawing my own face off on my list of interests.

I even let a few things go that I wouldn't with men my own age. For one, "cats." The twenty-one-year-old uses the word "cats" to describe jazz musicians. Unless you played with Count Basie and follow it up with the word broads, or you have three teeth and your time on this earth is so fleeting that you are allowed the word cats because you're about to meet the ultimate Jazz Cat in the sky, you cannot use this word. I let it go.

This is just for fun, I say to myself. Fun, I tell others. something to pass the time. Age is just a number. The sweet chick-lit lies start piling up, until I could be drinking a cosmo, reading Cosmo, with my rabid dog Cosmo.

We first kiss after a holiday party. I tell him my age, and he is undeterred. "That's okay," he says, inching closer to me at a work party. "I like cougars." I kiss him awkwardly in the elevator. We make out in the subway on the train downtown. I marvel at my skills of ripe seduction. Jesus, why am I such a goddamn stud? I turn down his initial offer to go home with him. A week later, he calls me to hang out.

But in that in-between week, doubt starts to filter in. Expectations, the serial killer of fun. When we finally meet, I get pissed-drunk in the first hour, to prove I can knock back drinks like, what? A seasoned alcoholic? What is this even? What are you, cowboy? What is that? He brings his friend along to act as buffer, in case he is guerrilla-attacked by my vagina.

Five drinks become maybe a couple more than five. Somewhere along the night, the vadge buffer slides off into the night. It's on. It's so on. It's… oh. Oh wait. Wait. What's this? Things have taken an unfortunate turn. He is more sober than me. We have switched roles. He is the adult, and I am the drunken twenty-one-year old doing a never-ending keg stand.

I run out of the subway car at four a.m. because I think I'm going to throw up on the platform. He chases after. Back at his place, with visions of forty-year-olds who can shoot rainbows out of their vaginas, I give the old passion one last try. "Do you know how many times I'm going to blow you tonight?" I ask. "What?!" he responds. Somehow it sounds so much sexier in my head, like something whispered by brazen women with really bad highlights. I follow it up with "I don't want to be, like, the crazy woman you had sex with," assuring I will always be the crazy woman he had sex with.

The future of our relationship is summed up on the subway ride back the next day. He kisses me on the cheek and utters the words, "It's been real," like we are in a '80s movie drinking cherry Slurpees. He is Val Kilmer, and I am Joan Cusack.

He explains a week or two later why we cannot date. "It's the age thing, and the work thing." He starts to sign off IM with "Awright, dawg, I'm out," a clear sign we will never have sex again. Before, there is sex. Now, there is "dawg." When God is feeling cruel, there are even high-fives. 

I have an ongoing fantasy about the against-the-odds relationship. We'll be like Harold and Maude, just not disgusting.

The truth is, I want these relationships to work.  I don't want to be the woman who talks with her girl friends later about some young guy's stamina over hyper-pigmented cocktails. That's more depressing than anything I'm trying to escape. At some point, the extremely low probability that these relationships will last makes me want them to happen more. I have an ongoing fantasy about the against-the-odds relationship. Lovers separated by age, time, wars, intergalactic space travel, Bronson Pinchot. We'll be like Harold and Maude, just not disgusting.

I want the parts of these men that are immature to match the parts of me that are immature, superimposed over each other like tracing paper. Except instead of tracing, what I'm doing is more like trying to copy the mouse off the back of the matchbook to get into free art school. It looks like a stoned meerkat.  

It is the younger guys who end it, usually with a slow fade. Despite their ages, they've already figured out what I am still trying to grasp. They don't want to redefine adulthood with me, nor are they blinded by a fantasy of what they want this to be. They're just trying to graduate from college.