Nice Try

by Josh Gondelman

  Before I go, I’d be remiss if I didn’t say this out loud for the few of you who will care: Weezer never quite makes the comeback album you want them to.

  It Was Funny at the Time

  During my senior year of high school, our drama club put on a forty-minute version of Shakespeare’s Much Ado about Nothing as part of the Massachusetts High School Drama Guild’s competitive theater festival (a.k.a. DramaFest, a.k.a. Fest).1 I played Dogberry, a bumbling constable, who is portrayed by Michael Keaton in the 1993 movie version of Much Ado. I thought it would be funny if I shaved male pattern baldness into my hair to look more like Michael Keaton. But first, like a good kid, I asked my parents’ permission.

  “Well, I don’t think it’s a great idea,” said my mom, “but I’m not going to tell you not to do it.”

  So obviously I did it. It looked, to say the least, unsettling. While my hair was growing back, I started wearing a winter hat to school. One day in the cafeteria our vice-principal told me to take it off. Didn’t I know that it was against the rules? I took a deep breath and removed the hat. He recoiled in shock.

  “We can make an exception,” he said.

  My dad, who comes by his baldness honestly, told me cryptically, “It’s not always going to grow back, you know.”

  There’s a photo of the two of us from that era sitting side by side that was funny at the time, but it becomes less so with every passing year. Time has evened our hairlines out, so they match in every picture of us now. But when I was eighteen, my hair returned in a few months, which is the only thing I miss about high school.

  Don’t Aim, Just Throw

  When health teachers and parents and very special episodes of TV shows tell you to wait to have sex until you are in love, they are giving you bad advice. And it is bad advice I made the mistake of following.

  Sleeping with someone you love is great. Sleeping with someone you love the first time you have sex is a great way to disappoint someone you love. This is especially true if that person has ever loved and/or slept with anyone else before. In that case, the thing you have saved for your first true love will wind up brief and sweaty and disappointing. Your lover will wonder whether he or she has just engaged in sexual intercourse, or missed a bus after running half a block for it and then smashed crotchfirst into a fire hydrant (not to scale).

  I grew up lucky enough never to get the message that sex was something bad or dirty. But I did, over and over, receive signals that it was something for grown-ups, a thing that you’d know when it was time for, something with consequences, like applying for a mortgage or adopting a puppy.

  “You’re not ready to be having sex,” my father told me offhand at one point in my midteens. At the time, he was probably right, and I took his words to heart. My dad has had sex, I reasoned. I was proof of that. He probably possessed some insights that I lacked. Still, both he and I spent my adolescence avoiding any deeper discussion about what those insights might be.

  Our original “birds and bees” talk took only a few awkward seconds. My dad was dropping me off at a friend’s house in a nearby town, and when we hit the highway, he turned down the sports talk radio that had been soundtracking our drive.

  “Do you ever think about . . . you know . . . girls?” he asked. A few moments passed. I couldn’t tell if he was asking if I’d started having sexual feelings, or whether he’d assumed I had and was inquiring about what gender I directed those feelings toward. In the background, men yelled at low volume about the New England Patriots.

  “Uh . . . yeah,” I replied. My dad nodded.

  He turned the radio up, and that was that. My dad was never dishonest about human biology. We just never felt comfortable discussing it with one another. It wasn’t his fault. I clammed up when the subject was broached. He may also have witnessed a dozen years of my general awkwardness and decided, “You know what, this kid won’t be needing any more specific information about sexual intercourse for quite some time.” He would not have been wrong to think that.

  My first introduction to human reproduction came from a promo for Roseanne, featuring this bit of dialogue: “We met at a bar. We had sex for hours, and now I’m pregnant,” said one character to another. Duly noted, I thought. That’s how that happens. My crash course in sex ed did leave out a few things, though. What “sex” was, for example. And the fact that you can have it without getting pregnant. Also, it would have been nice to know that whatever constitutes sex rarely happens for hours (at least, that hasn’t been my experience, for which I owe any previous partners a hearty “I’m sorry” and/or “you’re welcome”).

  In my high school every sophomore class spent an hour looking at the Massachusetts Pictorial Guide to Sexually Transmitted Diseases, which was essentially a book full of pictures of penises and vaginas and mouths and butts that looked like they’d been left in a Tupperware container in the back of a refrigerator and then forgotten for months.

  One health teacher at our high school told his classes that oral sex and anal sex could result in pregnancy through a Rube Goldberg–esque series of sex acts. I don’t want to get too graphic, but the likelihood of the sequence of events he described taking place was about as high as the potential for getting pregnant from playing water polo or feeding a goat.

  The curriculum also subjected us to an exercise wherein everyone in the class walked around shaking hands with each other, and the twist was that if instead of shaking hands, you had been having unprotected sex, you’d have probably had full-blown AIDS already, because when you have unprotected sex with someone, it’s like having sex with everyone they’ve ever had sex with. I mean, unless of course they used protection with previous partners. Or if you both get regularly tested between partners. Or you don’t subscribe to the puritanical notion that sex is something that automatically makes you soiled forever. But those are the things most people don’t learn in school, because many teachers would rather their students be terrified virgins than well-informed managed-risk takers. And never mind the fact that somehow having sex with every person in your high school health class would be an incredible accomplishment in the field of ravenous bisexuality that would make David Bowie blush.

  Good news for my health teachers: their plan worked on me, at least! The strategy of big-picture repression left a constant echo of fear in my adolescent brain. I internalized the drawbacks of having sex without weighing them against the benefits, which is a bad way to make decisions. It’s like never going to sleep because you’re too afraid you won’t hear your alarm, and you’ll be late for work in the morning.

  The problem with trusting authority figures’ proclamations that you “aren’t ready” for sex is that none of them ever circle back to let you know when you are. Not that I would have wanted one to. Receiving an explicit signal from my dad would have felt even weirder than radio silence.

  “It’s time,” he’d tell me, I guess, in this scenario. “Now go out there and throw it in some lucky lady . . . with her consent, of course.” Obviously, that’s not how my dad talks, but there’s no script for the “it’s time to bone, my son” speech, so I have no idea what he would say. Would he hand me a box of condoms with a sage nod? Would he wink while making that gesture where you move one finger back and forth through a loop you make with two fingers on your other hand? (Why is there not a word for that gesture? It’s so hard to describe in writing!) It is, looking back, probably for the best that my dad didn’t try to give me the green light for coitus.

  I’m relieved that my authority figures didn’t bombard me with admonitions to wait until marriage, but I did envy the clear point on the horizon for switching from “desperately rubbing your junk against another person’s nonjunk because that doesn’t count for some reason” to “doing regular sex.” I’m glad I didn’t wait that long; saving your virginity for marriage feels as arbitrary as never driving a car until your wedding night. I imagine there’s a lot of “Sorry to stop so short!” and “Whoops! I thought I’d fit into that space mor
e smoothly!”

  And what does it mean to be “ready”? When leaving my apartment, I’ve said “I’m ready to go!” and meant everything from “I’m at the front door!” to “I just need to put my shoes on!” to “I am basically still asleep!”

  In the context of sexuality, “ready” has an even squishier definition. Does it mean monogamous and in love? At peace with one’s own place in the universe? Or just . . . sufficiently horny? Even though I was definitely the third thing, I dragged my feet, unclear on what the ideal circumstances even constituted.

  To me, the idea of readiness superseded every other sexual concern. Concerns like:

  Did I want to have sex? (Yes, definitely.)

  Did people want to have sex with me? (Yes, inexplicably.)

  Did I have physical opportunities to have sex? (Yes, occasionally.)

  Did I understand how to have sex? (Yes, technically.)

  Through my late adolescence, I worked myself into such a frenzy viewing sex as a “leveling up” experience. I pictured it as the part of a video game where you’ve made it through a gauntlet of adventures, and you’re ready to approach some kind of giant spiky turtle and then, at long last, fuck that turtle (for the sake of this metaphor). I just wanted some reassurance that sex itself would help the relationship progress to the next iteration of dating.

  Sex existed as an abstract concept, which of course it was, because I wasn’t having it. In fact, I could barely believe that anyone was. In late high school, a group of classmates and I went with our significant others to one friend’s family lake house. When everyone else showed up late to lunch, I quipped, “Where were you guys? Doing it?” As I met my friends’ eyes, I saw that the answer, universally, was Uhhh, yeah. Duh. I was stunned. Aren’t you guys afraid of . . . well, everything? I thought.

  The longer I waited, the worse things got. Pressure intensified. My standards for the right moment and the right person escalated. My feelings for one girlfriend had already begun to fade by the time she put an offer explicitly on the table (or, more accurately, “on the extra-long twin bed in her dorm room”), so it would have felt wrong to increase our level of intimacy. Another young woman I dated in college didn’t seem to want a long-term relationship, so I felt reluctant to make myself more vulnerable by losing my virginity (gasp) to her. I had kissed a few other girls, too (I swear), but making out with someone at a party, or even having a long-running, sporadic hookup with a friend never seemed like the right circumstances for a first time. But in all those situations, either their first times had been in the past or they’d decided I was the right person for them. They were ready! Why wasn’t I? I let an undefinable concept of “perfect” become the enemy of, well, maybe not even “good,” but anything at all.

  My concept of sex as a transitional, transformative experience totally neglected it as an activity you actually do with your human body. And, like most physical talents, it’s something that you have to work at to perfect, and it’s not something that comes naturally to me, specifically. I don’t know why I assumed that although it had taken me years of practice to shoot a competent free throw, I’d immediately start having spine-tingling, soul-merging sex right away.

  Making love is the opposite of learning to drive or skydiving, activities during which you start with another person there and then graduate to doing it on your own. With sex stuff, you start alone, and then add another person later, which makes sense because the danger of falling twenty thousand feet to your death is (usually) minimal when you are masturbating. But knowing how to attend to your own body (at which I had become something of an expert, not to brag) only goes so far when you introduce a partner with her own set of needs and expectations into the mix.

  So, inexperience became a mounting impediment1 as the years went on, in large part because I hate being bad at things in front of people, which, I realize, is not a unique quality. Nobody is like, “Hey watch me fall off this skateboard!” But I hate it more than most people. I’d rather practice something a hundred times in private and then show off a version of it that I think is pretty good before I accept feedback. The aforementioned driver’s ed, for example, with an instructor seated next to you, foot on an extra brake pedal, was agony. Just let me noodle around in an empty parking lot, and if I hit something, fail me. I’d rather just be told I’m not good enough once, rather than over and over as I improve by increments.

  When I played sports as a kid, I resisted my coaches’ real-time input:

  “Choke up on that bat!”

  “Elbow in!”

  “Don’t aim! Throw!”

  “I know,” I’d seethe quietly. “Just let me try it again.”

  The last piece of advice was always particularly galling. “Don’t aim! Throw!” is a pitching maxim, the upshot of which is, “Don’t think too hard! Trust your instincts!” By nature, I am not a thrower. I’m an aimer. I think about things. Then I overthink them. And then sometimes, for good measure, I over-overthink them. I distrust my own instincts like they’re advice that was whispered to me by a nemesis. Are you trying to trick me, me? I wonder.

  The upside is, I rarely make rash decisions like getting face tattoos or making massive investments in cryptocurrencies. The downside is, I perform dismally at instinct-based activities like sports and sex, the latter of which is a lot like a team sport that you play with two people (or more than two, I’ve heard, sometimes, but if you’ve played it that way, kindly keep it to yourself).

  The more I treated my first time like a thing, the more of a thing it became. So while I searched for the perfect partner and optimal circumstances, I was unwittingly undermining the relationships I was in by leaving my girlfriends and dates as consistently unfucked as a husband in a 1990s sitcom. (“Come on, Debra! Shhh. The kids are asleep!”) And, as we learned from the show Everybody Loves Raymond—Except His Wife, Who Won’t Even Throw Him a Hand Job Every Once in a While, that takes its toll on a relationship.

  Also, I should say for the record, I was doing . . . other stuff. I don’t want to get into exactly what constitutes “other stuff,” because it’s gross to read about what a teenage boy (or, as I thought of myself, a teenage man) did with his penis. It was sexual, although it wasn’t quite sex, and it definitely wasn’t sexy. Suffice it to say, I was doing stuff I didn’t want my parents to know about, but nothing that would really have horrified them. Also for the record: I was not one of those people who “preserved” their virginity for marriage by experimenting with anal sex. (That is a real type of person. According to my observations, they often get married young, presumably to stop having so much anal sex.)

  In any case, way after I should have (i.e., in my last months of college), I decided that I’d met the right person. She was smart and funny and pretty and nice. Also, she still is; she hasn’t died. She didn’t seem to openly or secretly hate me. I didn’t fear making myself vulnerable to her. I was ready to level up, but I didn’t have the vocabulary. Fortunately, she did.

  After a few months of dating, she very maturely was like, “Hey, why aren’t we having sex?” And I explained my reasons, and she was very understanding and then we had sex, and it was emotionally very exciting and physically pretty much what you’d expect, and nothing was different afterward except we then had sex more times, which was also fun. Aside from that, though, everything stayed the same. Our relationship hadn’t gone to any next level. I didn’t have a deeper (hehe) understanding of love or humanity. Nothing was transformed in me or her or us. My girlfriend was a human woman, not a cocoon I crawled into as a boy and exited as a man, which is a gross metaphor, but it’s as close as I can get to explaining what I’d thought would have happened.

  That is, nothing changed while we were together. A few months later, though, we broke up. Of course we did. You don’t often stay with the person you lose your virginity to well into adulthood unless you’re a character in a Billy Joel song, and even then you still get divorced. One problem with deciding that someone is the “right person,�
� it turns out, is that when she isn’t, you end up shaken to the foundation. You lose faith in your own meticulous judgment and your prospects for future happiness. You cry a lot in your car. “You,” of course, means me.

  I wasn’t wronged by our breakup, but I had been wrong. Not about whether my girlfriend was the “right person” but about whether any person could bear the burden that I’d saddled her with in my mind. I’d thought I was finally ready, but how could I have been when our breakup had left me distraught and lonely? I, probably for the last time in my life, wrote some poetry that I never showed to anyone. It was embarrassing. I was on the wrong side of twenty to be having what was essentially a teenage breakup.

  Once I finished grieving (geez, I’m still so melodramatic about this), I finally figured out that there was no significant difference between having had sex and not having had it. I realized that every time you have sex is essentially your first time until you figure out what you’re doing. If you don’t know which way the condom goes on, it’s your first time. If you don’t bother with foreplay, it’s your first time. If you can’t locate the clitoris, it is definitively your first time. Obviously these specifics are not applicable for all genders and sexual orientations, but you should probably learn where the clitoris is just from an anatomical/medical standpoint. Unless your bodies lock into an immediate rhythm through a force of fortunate chemistry, every first time with a new partner is a first time with the potential to be as uncomfortable, but also as exciting and special, as your first first time.

  I plunged into my twenties having not just teenage feelings but teenage sex as well. I crossed the boundary that had been such a stumbling block for me, but that still left me basically right where I was before. You don’t go from virgin to sex genius overnight, in the same way you don’t pick up a guitar for the first time and start shredding solos. (Yes, I know that analogy doesn’t quite track, considering I spent high school and college shredding sex solos.) I had become infinitely more experienced, statistically speaking, while gaining only marginally more experience. And as withholding as I’d been with past partners, I was equally clumsy and bumbling with women after.