A Thousand Tiny Failures : Memoirs of a Pickup Artist

by Tony D

  I had a nagging fear though: In Montreal, I’d been prostituting in call centers… it was awful. Working those places was like smashing your nuts with stale baguette. You need to eat it to stay alive, but do you have to? I had first world problems. I didn’t care for installing stereos again, or working in gas stations, or warehouses, or any of the meaningless dead ends I’d subjugated myself to in my twenties. I remembered pulling graveyard shifts in gas stations, reading every magazine on the rack, drinking free slurpies, chugging shit coffee to stay awake, and then skateboarding home at nine a.m. The looks on the commuter’s faces as they went to their jobs—like a zombie movie. The terror of our entrapments; in the immortal words of Radiohead, “We do it to ourselves, we do.”

  Angst is a luxury of the western world. If I wanted a real future, not wage slavery, I’d have to focus on a skill and develop it. I’d been considering teaching pickup. I’d taught a few of my friends, but I’d never been crazy about nightclubs and would rather be remembered as an explorer, a thinker or an artist; not a man-whore. But I’d learned a lot about leadership, belief, freedom from outcome through taking action, and was somewhat of an expert in self-development. Most people read self-help books, but never apply the information. I’d been applying it daily for two years.

  I picked Carly up and brought her to my mother’s place. I had nowhere else to take her. I lead her out back to show her the tent, so she’d be comfortable staying there later. “It’s really quiet at night. You can see the stars!” I told her.

  “Doesn’t it get cold?” she asked, skeptical.

  “No, I have a really warm sleeping bag and we can cuddle.” I said, hoping I wasn’t pushing my luck with the cuddle comment.

  Carly met my mom and my sisters, and I could tell they liked her. I wouldn’t normally bring a girl to meet my family unless we were dating for like, a year. But what choice did I have? Anyway, I never felt that I was doing anything wrong. I think all men should try to be with as many women as they can. How can you know what love is, what connection is, if you’ve only been with one, two, or three girls?

  By this point, I’d been with over thirty and still hadn’t found love, if it even existed. Maybe I had to choose love and allow weakness; I would keep looking, and I didn’t care what anyone, even my family, thought about that. Now I look back, and I think that if I never sleep with another woman, I would be ok with that. I’ve had plenty of fun.

  We went to the tent so we could drink coolers. She made me watch a crappy chick flick called The Notebook. “It’s really good!” she told me.

  I could tell she was in love with Ryan Gosling. I thought the movie was sentimental drivel, but it got her into a positive mood. We kissed and I took off her clothes. She had a great body, her long blond hair and soft skin was exciting. I was finally going to bang this girl, I couldn’t believe it. I put on a rubber, laid her on her back and tried to get in there. I poked, and prodded and poked, but it just wouldn’t go in. I went into my backpack and found a little packet of lube. I applied it and tried again. I finally got the tip in. She was really tight. Slowly I pushed forward. Carly grimaced.

  “Are you ok?” I asked her.

  “Yeah. It’s ok,” she said through clenched teeth.

  I pushed again, but couldn’t get more than the tip in. I rubbed in and out, in and out, until finally she relaxed. I’d been taking it easy on her until I figured I’d just go for it and let her deal with the consequences. With a final thrust, I was in. Oh triumph and joy, what a victory, I thought. There’s something grand about getting inside a new, beautiful woman. I wanted to grab my spear and go hunting.

  I started moving at a faster pace, and buried my face into her blond hair—it smelled like coconut. Then I noticed she wasn’t making excited noises of pleasure, quite the contrary. I leaned back to look at her face and she was wearing a full mask of pain, like she was trapped in a torture chamber or something. I pulled out to look at my dick, but there was no blood.

  “Are you a virgin?” I asked.

  “No…” she replied, without looking at me.

  “Damn it looks like I’m hurting you. What gives? I want this to be fun for both of us.”

  “It is, ok. Keep going. I’m ok.”

  “Ok,” I said.

  I pumped away in a few different positions until I finished. It was the worst lay of my life. She was in pain the entire time. I realized that, for me, sex was all about the woman’s pleasure. I really get off on women when they freak out sexually, make lots of noise and really enjoy it. After we got dressed, I asked her to sleep over, but she had to work early so I drove her home. On the way she was very quiet.

  “Are you ok?”

  “Yeah I’m ok.”

  “Did it hurt?” I asked.

  “Yeah, but I’m ok,” she said, looking out the window.

  I dropped her off and she got out without a hug or goodbye kiss. “Wanna hang out tomorrow?” I asked.

  “Ok.”

  “What time?”

  “Whenever. I get off work at three.”

  “Perfect. I’ll see you then.”

  I watched her apple bum go through the front door. I felt the glow. I had a new potential girlfriend. The dry streak was over, and I’d captured a keeper. Hot, smart, young. I drove home and spent the night smoking pot, writing aphorisms and counting satellites. No masturbation.

  You’re the king. They’ll sing songs about you one day.

  The next day I woke up early, ran, sipped an Americano and chewed a bagel with cream cheese. Then I wrote an article, with the most-intimate details of my mighty seduction, and posted it on the forums. The nerds and gurus alike cheered with glee and toasted my success. I was a living legend—to about thirty-eight-hundred strangers. My pen name was Zardoz, after the sci-fi classic starring Sean Connery. He’s a savage from a barren land who infiltrates a giant, flying stone head, for whom his people murder for, and worship as God. Connery discovers to his horror that all of his life, he has been controlled by a society of masculinized, psychic women and bi-sexual men. Named The Vortex, encased in a force-field, it houses all the art and knowledge of humanity. He raises a violent ruckus and accidental sexual revolution. It’s the shit. I wish I was Connery, or at least one of his chest hairs—a silent witness to his majesty.

  Later that afternoon, I texted her to confirm our date, but she didn’t reply, so I called her a few hours later and got the same. I waited another four hours and texted again:

  “Hey, are we hanging out or what?”

  Still, no reply. Nothing is more infuriating as when someone doesn’t reply. I hate it. It’s just plain rude. Future girlfriends, should you discover this debaucherous tome, realize that for every unanswered text one kitten will be pinched, hard.

  At four p.m. I went for a drive down the beach, and there she was, strolling languidly with a girlfriend. I was pissed but also relieved she wasn’t with a guy. I parked for interception, and sat on a bench until she arrived. She stopped and sort of smiled.

  “How are you?” I asked, politely.

  “I’m doing good, you?” she said, also politely.

  “I didn’t hear from you. I thought we were hanging out.”

  She smiled, then looked at her friend, then back at me. “Yeah.”

  “Yeah,” I replied.

  “Well, I also had plans with my friend.”

  “We’re not friends?”

  She smiled politely. “Sorry, we gotta go. See you around Sebastian!” She said with uncommon formality, and that was that. Bitch-Tits redux.

  She walked away, and I sat there on that bench, a confused glob of beta-male. Was I cursed by ancient evil? Now this? Every woman I bang ends in disappointment and humiliation? What does a guy have to do? Love is a farce. Life is pain.

  I texted her a few more times with messages like:

  “I’m ready to continue our journey into the epic.”

  But she didn’t reply. I figured it all went to crap when I penetrated her. Maybe she wa
s embarrassed. Maybe she felt raped. I definitely didn’t rape her. I would never do anything to a girl like that. Not like that. Not unless she wanted me to in a Fifty Shades of Grey type of way. Women are brilliant and wonderful. I adore them and appreciate everything they’ve taught me about myself. But when they drop me like monkey shit I resent them—and the small hatred grows. But I get it. I’ve dropped plenty for the smallest infraction—and justification is the eldest of egoic children. I vowed do devote myself further to pickup and self-development. I was learning how to attract girls, but not how to keep them. The pattern was obvious. Empirical data does not lie. A beautiful young woman is blessed with sexual choice. I’m only blessed with my brain and ambition.

  My mom and sisters asked what happened to Carly. I didn’t know. They were disappointed. Maybe they hoped I’d get a girlfriend and stay in Penticton. My sister said I would have a new one by the end of the week. But it’s just not that easy. I’d cashed my lucky charms. At least I got laid, sort of. It’s far worse to be flaked on before you get the pussy. For a woman, her pussy is her Pikachu, her power source. Once she gives it up, she must resort to tears and jealousy to manipulate us. And I get it, we go inside you. That’s pretty weird. Pussies are weird, like, pink little alien pleasure tacos. And we want nothing more than to crawl inside, drill away and take a lovely, bearish nap on your heart. True story.

  To save money, and for kicks, I decided to hitchhike back to Vancouver. I’m lucky that a cool girl picked me up and not a cannibalistic man-rapist. She was going straight to the coast. She and her husband ran a boating adventure company at a lakeside resort. They had a tough first year, but now things were going very well and cash was flowing nicely. They just bought a new house and even though they had some hard times, were still very much in love. I told her I was a dating coach and planned to write a book about my sexual adventures. She thought it was the coolest job she’d ever heard of. I thought hers was better.

  She didn’t vocalize her judgment when I told her I hit on over a thousand girls. “Oh my god that’s hilarious,” she said. We smoked weed and I watched the mountains pass and the landscape morphed from desert to lush west coast rainforest. I ate a banana muffin, some beef jerky, and fell asleep.

  I awoke in Vancouver and peeled my face off the passenger window. I wiped off the grease stain, hugged and gave my see-you-laters. I stepped out into a gas station parking lot, and I was in Vancouver again. It felt like returning to an ex-girlfriend you thought you missed, until you got back together and found the same old issues. She was still pretty though.

  Chapter 27

  Vancouver (Same same, but different)

  It had been two years since I got my surgery, one and a half years since I moved to Montreal, and now I was back; more experienced, confident, and sexed. I moved around and crashed on various couches. One of my old friends, Dylan, let me stay with him for several days. I made him watch pickup videos with me. He found it interesting but thought it was a little creepy.

  “No dude!” I told him. “It’s only creepy if you think it’s creepy.”

  One day over beers he told me he preferred the old Sebastian. It hurt. I had a feeling that when I got back I wouldn’t be able to relate to my old friends. I was right. The guys I met still seemed the same: lost, broke, sad. I loved them but I was just getting started. I wanted to see the world, date hotter girls, do something impressive, get rich. Not smoke weed and go to rock shows where everyone stands around pretending they’re apathetic. I like live music too. I used to be part of that scene. But now it seemed boring and the girls were ugly compared to the ones I’d been dating. Luckily Dylan and I found middle ground at karaoke bars.

  One night we went to a local pub, and were looking over the song list when a big girl passed Dylan a note reading, “Hey. My friend the brunette girl thinks you’re cute.” Dylan handed it to me.

  “Bro,” I said. “Let’s go.”

  We walked to their couch and his girl was all smiles. Dylan is sort of shy, even though he’s tall, tattooed and handsome. He’s got that sad artistic thing going. He’s like my brother. I’d lived with him for three years before I left for Montreal, and we’d been through a lot together. Even though he didn’t approve of my obsession with picking up women, there we were doing it together. I did the talking.

  “We’re here to bring the karaoke party. I’m Sebastian. This is Dylan.”

  There were three girls; a dirty blond, elfish, bad fashion sense, and cute enough, a sexy brunette and a very pretty but terribly thick, (I mean obese,) girl. They were all in their late twenties and very open to us. The big girl shoved over to make space, cutting me from access to the blond. I squeezed into the tiny space beside her.

  “Are you a karaoke fan?” the big girl asked.

  “Of course. I’m a rock star. Are you?”

  “Totally. I’m waiting for my turn. I’m going to do Spice Girls. What are you going to sing?” she asked.

  The blond was smiling at me from the other side of the couch.

  “I’ve got something in store. Don’t you worry. Hey, what are your names? I’m Sebastian.”

  “I’m Tina and this is Regan” she said, pointing at the blond.

  I reached over and shook Regan’s hand first.

  Tina was very, very interested in me. She was aggressive like big girls tend to be. She played the twenty question game, “Where are you from? What do you do? How old are you?” Then she would laugh at my answers and squeeze my arms. Every minute or so I would look across her vast expanse at Regan, and she would be looking back. I could tell by the eye contact that she was interested in me. But when I tried to talk to her, Tina would shift her mass in between us, blocking my view, and ask me questions like, “Have you seen the new Harry Potter!?”

  Fat girls are often very aggressive gamers; they need to be to compete with the thin girls. “Hey do you want a drink?” Tina asked. I did, and she was off to the bar to get me one. I remembered the quote by Quagmire from Family Guy: “Fat girls need love too, but they gotta pay.”

  Tina wanted to get me drunk. A sound strategy, but now I was alone with Regan. I only had a couple of minutes to work it.

  “Are you a karaoke superstar?” I asked her.

  “A superstar? Ummm. Yes I am!”

  “Do you girls come here every week?”

  “This is our second time. Do you?”

  “It’s my first. But I love karaoke.”

  “What do you do?” She asked.

  “I’m an unemployed writer. I just got home from a trip to Montreal.”

  “I loooove Montreal. It’s so fun,” she said, reaching out and touching my hand to prove her enthusiasm. If a girl touches you with certain energy, it’s a green light. If you don’t move forward you lose momentum and game over.

  “Yeah, it’s the best,” I continued. “Where are your favorite…”and then there was a great compression as Tina dropped her two hundred pound frame in between us, and we were separated like Moses split the sea. Tina handed me a drink. I took a sip and almost coughed. “Is this a double?”

  “It sure is!” Tina said.

  We talked while Dylan sang Ring of Fire by Johnny Cash. I didn’t mind Tina. She had some charm. I was thinking she was even sort of sexy and caught myself looking at her massive breasts when she wasn’t looking. I like big boobs, but these weren’t real big boobs, these were fat boobs. They don’t feel the same as big boobs, they’re all soft and doughy. Still, I was considering her until she tilted her head back and polished off a half pint in one swallow, followed by a putrid, Homer Simpsonesque belch. Genetics my ass.

  Finally, Tina got up to sing her ballad. When she did I slid over beside Regan. This time I wouldn’t let Tina separate us. Regan was a funny girl. She’s a playwright and actress with a good sense of humor. She even let me practice my stupid palm reading routines on her.

  “You’re going to meet a guy that sings really, really well. You will want to make love to him all the time, but he makes y
ou buy him expensive dinners first and that becomes costly.”

  Tina returned from her song and tried to shove herself between us. Not cool.

  “Hey,” I said. “We were having a conversation.”

  Tina pouted. “Well we were having one too, before my song came on.”

  “Yeah I know. But I’m not here for only you lady. I gotta share the love,” I told her firmly.

  Tina pouted again, and then went to the bathroom. Harnessing my alcohol-fueled courage, I stretched my arm around Regan’s shoulder. She snuggled into me like a girlfriend would, totally natural. Nothing would keep us apart this time, not even a two hundred pound drunk sexpot in full ovulation.

  “I won’t let her destroy our love,” I said.

  I didn’t want tension. I looked at Dylan and he was playing with his girl. Two of us, three of them. Something had to give… something big. Tina returned from the toilet and captured us cuddling; her face fell south. She plopped down beside us and pouted up at the karaoke screen.

  “You two are going to have sex tonight,” Tina said.

  I just looked at her and smiled, sorry-like. I understand Tina! I’ve been you soo many times, and it feels soo good not to be you! I’m a bad man, a fantastic and horrible person. If your friend wasn’t prettier and thinner and equally receptive, I might have been down. But that’s how men work. That is real. This great matrix, it’s a battlefield littered with carcasses, brothers killing brothers, vultures circling the triumphant victors, licking their chops and squawking their complaints.

  Then she stood up and with one long gulp, polished off her pint and walked nobly out the front door.

  “Is your friend alright?” I asked, pretending to care, but before Regan could answer I heard, “Next up, Sebastian with… Love Shack!”