Things I've Learned From Women Who've Dumped Me

by Ben Karlin

  Alex, age twenty-three, was Wendy’s idea, but I didn’t object—not to Alex being there or to Alex going first or to Alex being so fucking hot. Wendy felt Alex should be first because Alex knew what he was doing and I didn’t. Alex elbowed me in the side and told me to watch him.

  I watched Alex like a dog watches steak.

  Then it was my turn. I remember thinking that Wendy’s vagina felt nothing like my right hand. It was . . . damper. More humid. And looser—much, much looser.

  I humped away at Wendy. Then I started to worry. What if I couldn’t keep it up? What if I couldn’t come? If I couldn’t finish, I feared Alex and Wendy would look at each other, say, “Oh my God, he’s gay!” in unison, and then Alex would beat the shit out of me for watching him like a dog watches steak.

  I kept humping, humping, humping.

  My concentration began to flag, partly deflating my erection, as condensation dripped onto my back from the top of the tent. I think Alex was getting frustrated—it was hot in that tent, and he was ready to split—but he was too gentlemanly a statutory rapist to leave before I finished. So Alex did something that I, at fifteen, figured Alex could do because he was straight. To help me get there, Alex reached between my legs and cupped my balls.

  It helped.

  I slept with Wendy in part to scandalize my family with my blatant, and unexpected, heterosexual behavior. I made damn sure my mother “overheard” my late-night phone conversations with Wendy, theatrically whispered; I left notes and letters from Wendy laying out for my brothers to “find.” I stayed out all night. My family had long suspected I might be gay—asking my parents to take me to the national tour of A Chorus Line for my thirteenth birthday didn’t help—but my family was Catholic and religious. So even though I knew I was gay, and even though everyone else knew, and even though I knew they knew, we also all knew—knowed? —that I was never going to come out.

  That meant I had to learn to like pussy. So I had to go out there and find a Wendy, a series of them, women I could fool, women I could take advantage of. And, yes, I was, at fifteen, taking advantage of twenty-one-year-old Wendy.

  These were my options: fake being straight or join the priesthood.

  While the big house, fancy dresses, and naïve altar boys were tempting, I had concluded the priesthood wasn’t for me. So even though I could never truly fall in love with a woman and even though every fiber of my being screamed “No!” it was my intention to live a straight life. I was going to find a slightly boyish, flat-chested woman, fuck her just enough to fool her, keep her busy with babies, and bang the occasional callboy on the side.

  But could I do it? Could I fuck a woman? Could I learn to like pussy? I had to find out before I married one.

  The first time I slept with Wendy was a success, it’s true, and I was relieved that I could do this thing. I could put my dick in a woman and leave it there until I came. But I also knew that it wasn’t enough for me to like pussy when it was full of some hot guy’s spunk, or some hot guy was cupping my balls and lying beside me. That set of circumstances seemed unlikely to occur with any frequency in, say, my anticipated heterosexual marriage. No, I had to learn to like how pussy smelled and how it tasted and how it felt all by its lonesome. Or learn how to tolerate it, like so many closeted gay men before me.

  Alex wasn’t around the second time I slept with Wendy. We were at one of her friends’ apartments, just two blocks from my parents’ home. This time it was just the two of us. We started making out. Wendy got undressed. I got undressed. And there we were, standing together, in the living room, the two us, bare-ass naked.

  I missed Alex.

  Wendy guided my hand down.

  I missed Alex more.

  Today third base is—what? Double penetration? Pegging? Sucking off a she-male in the backseat of your dad’s Hummer? In 1980 third base was finger-banging—it was a more innocent time—and I knew what I was supposed to do when Wendy placed my hand over her vagina. I slipped a finger in.

  Then two. Then three.

  It’s hard to describe the sensation, but I’ll try: It felt like I’d slipped my hand into a large, lukewarm piece of lasagna that had been stood on its side. Only this lasagna had a pulse.

  And hair, this lasagna was covered in hair.

  I kept my fingers in Wendy’s vagina long enough, I hoped, to give her the impression that I liked hairy lasagna as much as the next guy. Then I executed what I, at age fifteen, thought was an exceedingly smooth move. I removed my fingers from Wendy’s vagina and pulled her into an embrace. I brought my hand up her back slowly. I caressed her—but just with the palm of my hand and my thumb and pinky, the fingers that hadn’t been in Wendy’s vagina. I brought my hand up to her shoulder. I leaned way in to kiss her neck, positioning my nose so it was angled over her shoulder. I brought my wet index, ring, and middle fingers up to my nose.

  You see, back in the tent I hadn’t really got a chance to smell Wendy. By the time I got in there, Wendy already smelled like Alex’s sweat and spunk. Not that I’m complaining, but the whole point of my adventures with Wendy was, well, learning to like pussy.

  Wendy’s vagina smelled awful. Really awful. Like no hairy lasagna I’d ever eaten.

  I need to take a time out here.

  For the record, I really don’t mean to be ungracious about Wendy or her vagina. I want to make it clear that I’m not stating Wendy’s vagina smelled awful. Although that is, um, precisely what I just stated. Hey, maybe Wendy’s vagina smelled bad—maybe she had a yeast infection or something—but it seems likelier that the problem wasn’t the vagina itself but the person smelling it, aka the vagina-smeller.

  We know more about sexual orientation today than we did in 1980. For instance, no one knew way, way back in 1980 that gay men’s brains respond to male sweat, scents, and pheromones the same way straight women’s brains do; nor did we know that gay men’s brains respond negatively to female scents, pheromones, and sweat, the same way straight women’s brains do. Researchers in Sweden added that interesting new item to the ever-growing mountain of evidence that homosexuality is genetic, not chosen.

  Okay, let’s get back to the hairy lasagna. . . .

  After quickly pulling my fingers away from my nose I began to caress Wendy’s back again. But this time I used all my fingers. I was pretending that I was passionately caressing her when I was, in fact, vigorously wiping her juices off my fingers. I thought this sequence of moves—strip, finger-bang, caress, position nose, bring fingers to nose, smell fingers, wipe fingers while pretending to caress—was pretty slick.

  “Did you just wipe your hand on me?”

  “No,” I lied. And then we had sex. No sloppy seconds for me this time. Tidy firsts. And I could do it. I didn’t need Alex there, my balls in his hand. I could do this thing; I could have sex with women. I could pass.

  We fucked around a dozen or so more times. Summer turned into fall, fall into winter. Wendy soon noticed that, despite her coaching, my sexual repertoire was shrinking, not growing. I ignored her breasts, I kept my fingers out of her vagina, my mouth never ventured south of her collarbones. Then one day Wendy called with two important pieces of news. First, it was over. Second, she had missed her period.

  I spent a week flipping out about the injustice of it all. How could I have gotten her pregnant? Didn’t shutting my eyes and pretending that Wendy’s vagina was the ass of this boy I was in love with offer any protection at all? Why didn’t my gay sperm, realizing where they had been deposited, turn tail and start swimming in the opposite direction of her eggs?

  I didn’t have to stress for long. The next day Wendy called to tell me she got her period. She also wanted to let me know she was seeing another guy now, someone her own age.

  “It was fun,” she said, comforting me. “I like you. You’ll meet another girl.”

  God, I hope that never happens, I thought to myself, listening as Wendy let me down easy. It wasn’t fun. I can’t like you or any girl the way I’m supposed
to. I thought I could do this, I thought I could fake it. I thought I could pass. But I can’t, I don’t want to, it’s not fair. My heart isn’t in it.

  A month later I had sex with a guy for the first time. In his apartment, in the middle of the night, in the middle of my sixteenth year. Jeff was twenty-one, with shaggy brown hair and big blue eyes. I guess he’s just another of the statutory rapists I have known and loved. Jeff smelled great. He tasted great. And no one needed to cup my balls.

  Lesson#15

  Nine Years Is the Exact Right Amount of Time to Be in a Bad Relationship

  by Bob Odenkirk

  This is a transcript taken from a recent Bob Odenkirk Rocky RelationShip Seminar.

  Hey. How are you doing, couples? Are you all ready to hear about my plan for you to get the most from your rocky relationship? I see one man over there who isn’t nodding. Sir? Oh, you’re a lesbian? Oh, I thought you were a man [really awkward laughs]. You’re here with her? Oh, I thought she was a man, too. I thought you were a gay couple. No, I understand you are gay, just . . . well, okay, let’s keep moving on.

  As I’ve promised in my brochures, I speak from experience. Everything I am about to share with you is based on real-life experimentation. My theory has been tested in the lab called “My Past” by a doctor named “Me.”

  Is there a time limit for relationships? How long do you “hang in there”? What’s a good “rule of thumb” for exploring every avenue before breaking it off and moving on?

  The answer is simple. Nine years.

  Now, I see a lot of heads not nodding at that. Probably you’re thinking nine years is overdoing it, especially if you broke up for the first time at one and half years and then broke up again at five years and then, even though you were living in different cities thousands of miles apart, you somehow forced yourselves together again for another four years of difficult unpleasantness. Many people would say three years of general unease is enough, that it’s time to “move on.” No. You’re wrong. You’re wrong and you’re pathetic. Nine years, you bitches. Nine fucking years. Who’s laughing in the back? That was a cough? I fucking hope so, because goddamnit I am speaking from some hard-won experience here and you’d better respect that shit.

  Here, my friends, is the only path to a “healthy breakup.” Though before I proceed, I would like to remind everyone that this seminar is 100 percent nonrefundable.

  Year 1

  This is the year of “The Crush.” Excitement, energy, warmth, and hope infuse every aspect of the relationship, making the possibilities seem limitless, rosy, and un-put-downable. Not much to say beyond that.

  Year 2

  Some afterglow remains. You begin to perceive shortcomings in your partner’s psyche, which will severely limit your ability to grow as a couple. You get pissed. You argue. Roses make things better. You start to notice how good food tastes, how interesting books are, how marvelously distracting distractions can be. Men might rediscover masturbation and think, “Hey, I’m a pretty good masturbator!” Your relationship is tumultuous, but in a classic pop song sense—this is pretty fun, actually, you sort of feel like a tortured artist, except you’re not creating art. Nor will you.

  Year 3

  Your friends tell you to get out. Her friends tell her to get out. You relearn each other’s emotional limitations and psychological shortcomings on a daily basis. An hourly basis. You consider therapy. This is good. This is the beginning of a choice growing inside of you. But you are still five years away from therapy! So slow down! The drama of the relationship is tarnishing, which makes you suspect that it is not actually made of gold, but brass. Here is what you will find out: It’s not even brass. Your relationship is made of mold, what you are seeing as tarnish is actually just more mold breaking down and feeding on itself. Fuckin’ mold, dude [uncomfortable coughs from the back of the room].

  Year 4

  A pretty good year. Some ups and downs in the relationship. Mostly downs, though. Even the ups are a bit downish. You are using this year to see if you can make your partner’s shortcomings work to your advantage. Good for you. You will fail. People around you are “clamming up.” They tolerate your relationship like they tolerate the clanking sound in a car engine. After a while it’s just there, no reason to acknowledge it. You go on a trip with friends, without your partner. You have a real good time.

  Year 5

  Your mother tells you to get out. You begin to consider divorce, but then realize you aren’t married yet. You think, well, maybe we should get married and with that commitment we can finally relax and let go of the “fantasy” of a happy relationship but find happiness in reality and a promise of undying okayness. And if that doesn’t work, then the divorce thingy is a legit option. You are also entering into the arena of long-term relationshippery. You are sort of proud of this—good, go with that, you’re going to need every bit of momentum you can get to make it through FOUR MORE FUCKING YEARS.

  Year 6

  You are going strong, avoiding each other, not asking too much from the relationship. Many of you might think this is the time to move into therapy, to actually confront the many issues that make day-to-day life unpleasant and long-term plans unthinkable. Too soon! This bad relationship needs to run its course, and it is a marathon. If therapy tells you to leave now you will be prematurely abandoning the race—in its final push to the finish. Plan a long holiday. It will not be enjoyable. Attend a wedding for friends who met only two years ago. Look at them and wonder. You and your partner are now in sync, sharing a low-grade depression which swarms around you like hundreds of depressed bees. This is a good year to discover the artwork of Edward Hopper. There’s something about his clean lines and composition that will speak to you.

  Year 7

  Same as year four. Three hundred sixty-five days, not that long as it turns out.

  Year 8

  Just doin’ time. You’re almost there. The couple who married a year and half ago after only being together for two years before that—they get divorced and don’t seem too distraught over it. By the end of the year they will both be in new relationships. Wow. That’s tragic. I guess some people are shallow. They have shallow relationships that start fast and end fast because they just aren’t that deep. They aren’t as deep as you, you tell yourself, at first confidently, and then, less so.

  Year 9

  The watershed. You can go to therapy now. Together and apart. You can do all those things you’ve been dreaming of: crying and collapsing on the floor, crying on the phone, crying in a restaurant. You can finally say, in public, “I think this has to end,” and watch the unstartled faces of your bored friends as they try to care. Give your friends multiple chances to care. They will need them. Start to separate your nine years of memories, furniture, and collections and realize it’s not that hard to do. It’s fairly easy to acquire the Seinfeld box set and an Irish knit sweater you both wore. As it turns out, the Irish can’t stop knitting. Spend that first night alone. The ghost of your ex wanders the halls. Don’t give it any credence because ghosts aren’t real. Not like vampires, which are very real, but not relevant to this particular discussion. I’ve said too much.

  [Long pause, more coughing from the back, the sound of a few people getting up and filing out]

  Great. You see that plan? You see how complete it is? How it covers every base? Here’s the great thing about the plan: It leaves you squarely sure that you will never enact this plan again. You will have a level of certainty in your life few people ever achieve. You will also have a high horse to ride as you comment on other people’s short-lived traumas. Oh how many times you will win the argument when you say, “Hey! Try hangin’ in there for nine years!” Nice. You can rest assured you tried everything, including depression and deep boredom, two flavors which must be sampled if you want to feel you truly lived. Why the hell do you think people climb Everest? Because it sucks BIG TIME! They did it anyway, and now they can rub that in other people’s faces for the rest of their lives
. You wimps.

  [Light applause]

  Lesson#16

  A Dog Is No Reason to Stay Together

  by Damian Kulash, Jr.

  Amanda was my best friend’s girl. Or at least he thought so. They’d had a brief fling eight months prior, and Adam’s M.O. at the time was to convince himself he was deeply romantically linked—like right on the brink of marriage—with whomever he’d last got it on with, regardless of how much alcohol had been involved in getting to the get-on, or how much time had passed since it’d been got. Every so often he’d run into his soul mate at a party and she’d have to ask for his name again, which made for awkward moments. Adam was my roommate, and I hated seeing him brokenhearted all the time, but Amanda was foxy, and since a guy is only obligated to respect another guy’s boundaries when they aren’t imaginary, I figured I was on stable ethical ground when Amanda and I made out after that fateful night at the monster truck rally.

  We were a great couple. We dressed funny and made art and took road trips and got drunk a lot. We moved to Chicago together and filled a loft with armloads of amusements from the science surplus store, and we invited our friends over to drink wine with us and laugh at religious people on TV. It was love—love like you see in movies. Except in movies, relationships don’t change, or grow, or slowly fall apart. They either last forever or end mercifully fast with a thrown plate and a jump cut. At least in the movies I watch. I suppose Hugh Grant fans could argue there’s a whole genre of film built on themes like “Now I Can Truly Love You Because This Maladjusted Boy Has Cured Me of My Selfishness,” or “All I Wanted Was for You to Say You Were Proud of Me and My Equestrian Accomplishments.” But the movies I watch and the books I read and the music videos I’m not in are all soft lenses and hot sweet love until something suddenly brings it to an end, like, say, the Terminator strolls in and impales the male lead.