A Thousand Tiny Failures : Memoirs of a Pickup Artist

by Tony D

  During my time living with him, I picked up a crazy nineteen year old named Samantha. It took me a month of texts and Facebook messages to finally have her meet me. I had to go to her house five times before she let me bang her, which for me, was a lot. She stopped letting me fuck her because she figured I was too old for her. Then I picked up a twenty-nine year old French girl who wouldn’t fuck me until I met her friends—so I met her friends and they all spoke French so they ignored me, and she stopped seeing me. Then I picked up another eighteen year old at a café by asking her about her book. She was reading The Diary of Anne Frank. I told her I used to sleep in a secret annex for fun. That got her. We didn’t last long. She was Jewish, I wasn’t. Then I picked up a twenty-one year old ballet dancer. She had the best legs ever, but just wouldn’t stop shit testing me with, “You should get a haircut. You should get a good job. You should blah, blah, blah,” so I ditched her. She wasn’t hot enough for me to deal with that crap, or so I told myself. Then I picked up a short haired twenty-five year old at a dance party. All I did was reach out, grab her hand, and pull. That was that. She took me home, did all the work, gave me a blowjob on her couch, and kicked me out. Never heard from her again. And it went on, and on with the girls, the phone numbers, the parties, the after parties, the bands, the festivals. And all this time I still got up every day to work in the Call Center of Doom.

  Montreal wasn’t the place for permanent residence. It was a fantasy world of debauchery and short term relationships. At least it was for me. Finally after one and a half years in Montreal, I was getting results. But even though I was having all this sex, I was lonely.

  I mostly hung out with Jeff and another guy, Charlie. Jeff was a good wingman and Charlie was good enough, a really smart dude. Charlie was a friend of Mark’s, and told me a story about how he painted this girls house in the hope that she would fuck him. “Friend, there’s a better way,” I told him. A few days and a few e-books later Charlie was a devout follower of all things pickup.

  “It works!” He exclaimed.

  After a few weeks of going out, he picked up a girl at three a.m. on a street corner. She had no money for a cab, so he took her to his house. A few weeks later, he slept with a nineteen year old blond girl he met at a party. Game worked, and I’d taught him.

  Prior to meeting me, he hadn’t wet his wiener in twelve months. All he needed to do was quit being so… pathetic. Charlie remains my friend to this day. He ended up dating that girl he picked up on the street corner long term. She was crazy and alcoholic, go figure. But because of him, I gained confidence in teaching.

  One day I got an email from my mother, telling me my sister was getting married. I got on the Internet and bought a one way ticket back to B.C. I was homesick. Montreal was a good time, but I was an outsider. I wanted to know if everything I’d learned would be applicable back home. I wanted to show my old friends the new me.

  On one of my last nights, I posted a notice on Facebook:

  “Friends. I’m leaving. Montreal was great but my adventure ends here. Buy me a beer tomorrow at Bar Biftek. Love Sebastian.”

  The next night I sat there in the bar waiting like the Godfather, and random people would show up, buy me a beer, hug me and leave. I counted them, twenty-seven in total. It felt good to be popular. When I left at the end of the night, I had a girl on my arm and fifteen friends and acquaintances chanting, “Sebastian! Sebastian! Sebastian!” Most of them I cold-approached, or met through people I worked or lived with. Eric stopped by and bought me a beer. “I’ll miss you man!” He looked skinny and paler than usual. He told me he was going to live on a raw food vegan commune in Alaska. Good for him. Mark didn’t show up, and neither did Olivia, or any of the girls I’d banged. I’d been in Montreal for just over a year.

  I couldn’t fall asleep that night, laying there listening to my girl-of-the-moment breathing softly. I didn’t want her. Her breath was bad and she needed to lose weight. What’s wrong with me? I thought. Why am I still fucking sad? Why do I feel lonely? Do I always need a warm hole to feel good about myself?

  I had a great night, threw a party in my name, banged a willing woman and I feel empty? Maybe I don’t even care about women. Maybe all I want is attention and validation. I looked at the girl and she started snoring. There was a little bit of drool coming out of her mouth, onto my pillow. I pushed her over and tried to fall asleep. I needed to get up early to catch my flight.

  “Goodbye Montreal,” I whispered to the dark.

  Chapter 21

  Penticton (Small town sluts)

  On my way back to Vancouver, I stopped in Penticton for my sister’s wedding. My home is a small tourist town in the interior of British Columbia, Canada. It was carved out of the mountain by an ancient bastard of a glacier that over a five thousand year melt crawled its way to death (transformation?), leaving a desert valley and two magnificent lakes on either end. When I grew up here, an insecure, creative kid, I didn’t think I would ever leave. I feared I’d meet a nice girl and knock her up. Maybe I’d slave in a lumber mill, or a seafood restaurant. It wouldn’t be an unfortunate life—but not the stuff of legend or song.

  I met my mom and sisters again. It was nice to see them. They asked about my trip, but I couldn’t tell them what I’d really been up to; they wouldn’t understand. They asked if I had a girlfriend yet. I told them I didn’t plan to get married, or have kids, so they would need to make twice the babies. They just laughed. They’re so cool.

  Alexandro used to harass me about it, “Man, don’t you want to have kids one day?”

  “Why?” I’d say.

  “Why? Because that’s what people do.”

  “Nah. I want to travel, make romance, adventure, fame.”

  “You just haven’t met the right girl. One day you will and you’ll want to put a baby in her.”

  “Fuck that. I don’t want it. I can barely afford rent, never mind a baby. Maybe I’ll get fixed.”

  “You’re crazy. You’ll have kids one day.”

  “No I won’t. What’s in it for me?”

  He thought for a second.

  “Who will take care of you?”

  “Money.”

  “No one will love you.”

  “My brothers, nieces, nephews, sisters and their children, and all my ex-girlfriends and their children will love me.”

  “Ha ha. Man, you’re a crazy man. Don’t you want to get married?”

  “No. I will never get married. It’s madness. I’ve got nothing against being with one woman for eternity and beyond, but marriage makes no sense for me. I’m not a huntsman in the Sudan, and I don’t need some priest or lawyer to write a contract stating if I fall out of love I must fund my ex-woman for life.”

  “Ha ha. Fuck Sebastian, you’re crazy. You’ll see. You’ll meet the right one. You just haven’t met her yet.”

  He’s wrong, you’re right.

  “Love is transitory.”

  “Whatever man. You’ll find her.”

  And at least once a week we’d argue about whether or not I’d have babies. But I just didn’t see the point of marriage or children. Sure when you’re old and feeble you’ll have someone to wipe your ass and feed you porridge. You’ll get to watch your younglings grow up bright and strong—and then, well then comes the disappointment. They decide to sell pot for a living, or they’re lazy, or they get addicted to video games and they end up hating you for being a parent since you represent oppression, and the ideals of a generation they have nothing in common with. Book Readers, they’ll call us.

  Eventually, after fighting about their fucked-up lifestyle or their choice of friends, they’ll scream, “Fuck you Dad. I hate you!” and run away—only to contact you when they need money for food, drugs, or shelter. In the meantime your wife grows fat, cuts off access to her vagina, and you retire into a placid spiral of suburban torpidity. Yeah. No marriage or children for me.

  Chapter 22

  Les Trois, Part 1: Carly

  (Lu
ck is a quantum anomaly manifested by desire + action)

  Ok, let’s talk about me and how awesome I am, again. Montreal was my nest, and I fell like the runt until my feeble wings would flap. One day in Penticton, I picked up three different girls; proof that city women are spoiled with choice, and that small towns would be easier. The first one I pulled out of a coffee shop, another off the beach, and the third from a bar. The barista was Carly. She was eighteen, tall, blond, and incredibly pretty. I scouted her behind the counter, and asked for the bathroom key. Then I said, “Hey. What do you do for fun in this town?”

  “Me. I just go to the beach,” she said, all smiles.

  “So you like to swim. You’re not a Pisces, are you?”

  “No, I’m an Aquarius.”

  “Ahhh. That means you love water, you’re a good friend, very loyal, and sometimes a bit neurotic.”

  “Ah!” She pouted. “I’m not neurotic! What’s your sign?”

  “I’m a Pisces.”

  She passed her co-worker the latte she was working on. “Oh,” She said, and gently stroked the nozzle of the cappuccino machine with a rag, “what does that mean?”

  “I go with the flow, the water. I’m an artist, and perpetually chasing something that eternally eludes me.”

  “Wow. So you’re… confused?”

  “More indecisive, but I know what I want. I’ve been sort of working on myself.”

  “What’s that,” she said, now totally focused on me, “that you want?”

  I closed my eyes and made a pained expression.

  “To… take a leak.”

  “Asshole!” She laughed. “It’s over there.”

  I went to the bathroom and glanced back. Carly and her co-worker were huddled, whispering and peeking at me. Excellent. Girl talk. As long as it wasn’t about how creepy I am, I was in. I returned for my Americano.

  “Well take me to the beach when you get off work. What time?” I asked.

  “Umm, ok! I’m off at four.”

  “Sweet. I’ll see you at four.”

  It was never this easy in a city. I love eighteen year olds; so willing to try new things. Am I a filthy bastard? Well, I’m not old enough to be her dad yet. I just can’t help being attracted to young women; they’re so fun and youthful and adventurous and hot, and nobody will know but me.

  Fuck the haters, seriously. Maybe we’ll fall in love. Maybe love isn’t just a chemical reaction biologically programmed to initiate pair bonding. Maybe not.

  Good work up there son. Keep it up.

  It was only noon, so I drove to the beach and parked my mother’s Toyota. I got out and scanned around. The three kilometers of beach were completely deserted except for the seagulls, so I sat on the hood and relaxed in the sun. So this is life, not bad, not bad. Then, a mirage, I scouted a lone figure in the distance walking along the beach. It looked like a girl, moved like a girl… it was a girl! And a cute one! What luck. I always believed in playing the odds. It’s better to have two chances than one. I waited for her until she was passing by. I stared at her, locking eye contact, and she smiled… a pretty one.

  “You could have brought some friends with you,” I said. “I was getting lonely on this big beach all by myself.”

  She laughed. “You don’t need anyone. You can still have fun by yourself.”

  “In theory. But hey, it looks like we have each other. Hi, I’m Sebastian.”

  “Liz, “she said, moving in to accept my behind-the-back low five.

  We chatted for several minutes. She was a bartender, twenty-three, from Toronto, and here for the summer. She liked wine and snowboarding. We agreed to meet later that night for a drink. It was really that easy. I didn’t have to insult her, or turn my back, or run any memorized script. I was chipper—her? Alone, horny, lonely, who knows? So it was on. I don’t consider myself incredibly good looking, or very lucky. I just know how to capitalize on opportunity where most men would defeat themselves in their mind before even trying, the poor fools—clipping their own wings.

  Four o’clock rolled in so I picked up Carly, and drove her to the beach. She’s a bubbly and enthusiastic type. Her cheeks would glow a youthful pink when she smiled. She was training to be a fitness consultant and worked part time at a gym, when not serving lattes to tourists. It showed in her strong legs and lack of body fat.

  I asked her to lie on the grass with me and point out the shapes and creatures in the clouds. No logic allowed. All that frustration and work so I could stare at clouds with pretty girls. Montreal was worth it, pickup was worth it, life is worth it.

  “That one is an elephant,” she said, pointing up.

  “That one is Hitler riding a Unicorn sliding down a rainbow,” I said.

  “Oh my god! I see it too!”

  After a few minutes of this, I turned my head to gaze romantically into her eyes, leaned in and kissed her. She was terrible at it, gnashing her teeth into mine, licking the roof of my mouth. It was as if she’d never kissed a man. I imagined what my pecker would look like going through that meat grinder. Grimace.

  She had to go home, so I drove her and sat low in the seat so her parents wouldn’t call the police. I could see the headline, “Dirty pickup artist seduces eighteen year old barista who can’t kiss.”

  Even though I felt like a bastard, I liked this girl. She didn’t seem immature at all, and she was gorgeous… a real knockout, like a heroine in a Hemingway novel. I could see myself staying with this girl. Maybe she would move to Vancouver with me.

  After our date I drove her home and we agreed to meet again as soon as possible, because I’m freakin awesome.

  Chapter 23

  Part 2: Liz vs. Dianna

  (The supreme art of war is to subdue the enemy without fighting)

  Liz showed up in her car at nine pm. My Sister peered through the window and said, “She’s pretty Sebastian! Where did you meet her?”

  “She’s an old friend.”

  “You haven’t lived here in ten years. She looks twenty years old.”

  “Amazing isn’t it!” I replied, walking out the door, slightly embarrassed and proud at the same time. Is there a word for that? Hey guys, don’t care what anyone thinks of you, except your sisters.

  Liz was wearing a tight pair of jeans and a black tank top that showed off her tiny waist and round hips. I hoped I’d get a better look at her that night, if I didn’t mess it up. My game plan was simple: Be cool, funny, aloof, and outcome independent. And drink.

  We drove to the bar and went to the patio over-looking the nighttime beach line. I was surprised to find a dozen of her restaurant co-workers there, eating and drinking on the patio. I felt played because I thought we were on a date; now I would have to win over her friends too. I introduced myself but they mostly ignored me. All the guys were fit and good looking preppy types. I knew these sorts. Penticton is a hockey town and jock types are everywhere. They were natural, physical alpha males—big, but not too smart. I felt insecure again. Again, I don’t like being the new guy amongst old friends, not when I’m trying to hook up with a chick. I want to be the guy with the social value; I want to bring her into my world so I can work my magic.

  Liz was ignoring me and flirting with a goateed line cook. I sat down beside her at the table.

  “Hey, introduce me to your friends,” I said.

  “Oh Mike, this is Sebastian.”

  “Hey man. How’s it goin? How do you know her?” He asked.

  “We met on the beach today.”

  He looked at her, then at me, with his mouth open.

  “No shit! You picked her up?”

  “He didn’t pick me up!” She said, punching Mike in the arm, letting her hand linger on his bicep.

  “Well Mike. A woman can’t be picked up because it’s actually her choice, we’re just friends.” I emphasized, “friends.”

  The ducks quacked in the water.

  “Well looks like we have a cockfight!” Liz said. “Don’t worry Mike… you’re winn
ing.”

  Mike scowled at her, “Hey relax.”

  Enough of this. I excused myself to use the washroom and walked into the bar. If she’s going to play us off each other I’d find another date. I’m a professional dick wizard. I approached a few couples in the corner that were playing a game of pool. I played a round with one of the girls while her boyfriend stared at me hard, so I excused myself and moved on. Near the bar there was another pretty girl sitting by herself and a fat middle-aged dude in a track suit was leaning across the counter, almost on top of her. She wasn’t comfortable. I moved closer to hear them.

  “You are soooo pretty. What’s your name?” he asked, waving his highball in her face.

  “Ummm, why?”

  “So I can buy you a drink, that’s why, hehe,” he said, his bulbous gut bouncing as he chuckled.

  “Ummmm, I like, have a drink,” she said, obviously irritated.

  “What’s your name babe?”

  “Dianna.”

  “Where are you from Dianna?”

  “I live here.”

  “Cool! So do I, hehe, hehe.”

  My inner White Knight raised his long sword. Dianna was hot. I decided to save her from this creepy douche. I approached her from the front so she could see me coming. We made eye contact and I gave her an over-exaggerated wink before closing in.

  “What’s up Babe? Sorry I’m late. You look fantastic. Who’s your friend?” I said, and then turned to look at the obese track star.

  “Oh, I don’t know this guy,” she said, playing along.

  “Hi. I’m Sebastian, her boyfriend.”

  He looked at her, then at me. She smiled at him and nodded her little head. “Oh, sorry man. I didn’t know,” he said, bowing out.