A Thousand Tiny Failures : Memoirs of a Pickup Artist

by Tony D

  So I had a girlfriend. My epic foray towards being a player was ending with my first conquest. But I’d already purchased a non-refundable ticket to Montreal. I told Esther about my mission, how I would be gone for at least a year. She didn’t really seem all that disappointed. I guess hot girls know they can find another guy relatively easily. Now I think she was faking it. She worked hard for me too. We met once more, fucked at my house, and I waved forlornly as she drove away in her little red Civic. It felt shitty because I really liked her, but I knew that in the long run my great adventure would bring me more joy than domestication ever would. But still, I was sad. I actually cried. I got naked and danced to The Smiths with my dick between my legs. Don’t tell anyone.

  That week I gave my notice at work. My boss couldn’t understand. He said, “Sebastian, you finally start to work like a man, after all this, and now you’re leaving?”

  “You told me I was a writer.”

  “That was before you became a good employee.”

  I knew that I needed money to start in a new city. That sense of urgency had compelled me to work twice as hard. I’d gained a lot of respect from my boss, but I didn’t want to install televisions for rich dickheads any more… it made me feel like Piggy in Lord of The Flies. A man’s work should fulfill his soul and give him a strong sense of purpose. I wanted to seduce beautiful women and see the world. I wasn’t sure about work yet. I needed money… that much I understood. Not much, but no amount of money would keep me somewhere I didn’t want to be.

  My friends were bummed out but happy for me. I felt bad for them, but I was happier for myself. I saw in my friends a lot of potential they would probably never realize. I had to move on and grow.

  I spent one more night smoking and gaming with my roommates, and the next morning I left for the airport. I love that feeling of uncertainty—not the sleepless nights and nervous shits, but the feeling of upcoming adventure. Every time I overcome a fear of the unknown, I become stronger. I’d lost a girlfriend, a social circle and job security—but I’d gained a future of joy, terror, growth…and debauchery.

  Chapter 6

  Montreal 2008 (Pre-Mayan Apocalypse).

  It took five hours for the plane to reach Montreal. Flying scared me, a lot more than hot girls, which is funny because I when I was a kid I wanted to be an F-14 pilot, like Goose and Maverick flying upside down, flipping off the Commies. Like, when the nerds became cool. Fuck you all, I’m flying a jet.

  We were hurtling at four hundred and fifty miles per hour, forty thousand feet up in a metal tube strapped to a rocket. When the plane hit turbulence and we bounced like shit in a tin can, I looked to the stewardess for signs of distress; she yawned and adjusted her bra. An old white man called her over to complain that his coffee was lukewarm. We’re in a fucking rocket, and this guy wants better coffee. The human race is doomed, for sure.

  There was a woman with nice legs a few seats behind me. I asked her if she was from Montreal, she said, “Oui,” and put on her headphones.

  When we finally landed with a screech, I kissed the wall of the Airbus and thanked the universe, or God, or whatever, for not killing me. It wouldn’t be a bad way to go, plummeting into Quebec soil and exploding in a fireball of fury. Quick and painless like, besides the mad descent. If I ever go down like that, I’ll laugh the whole way. It would be so absurd.

  Montreal was built around a central point, a big hill named Mount Royal. Under Mount Royal are two major universities, multiple colleges, and five major entertainment districts all within walking or biking distance of each other. Because of the low rent, liberal standing, and high culture, it’s a hub for artists, musicians, writers and partiers from around the world. It’s perfect for someone that wants to practice picking up chicks. Not only were the locals beautiful and friendly, but it’s a transient bohemian scene where young people come to escape their parents and reinvent themselves.

  I rode the bus from the airport to downtown. I noticed most people were dressed superbly. Even sixty year old women had more fashion sense than most Vancouver or Toronto girls. French women are beautiful. They have brilliant, thin bodies and big, juicy lips that puff out when they form their vowels. They’re supposedly notoriously easy to pickup.

  Legend has it that, in the old days, the fur traders from France had no chicks, so the Queen offered all the hot prostitutes land ownership in the New World if they would boat over and bang these dudes. So there’s a very sexually-liberated female tradition in place. Basically French girls are sluts.

  Good for them.

  I didn’t know anybody in the city, and that was fine. I first stayed with a group of Spanish kids who were fun. We went to parties and a few bars, but I mostly warmed up to practicing approaching alone. Anyway, their visas expired at the end of their semester, and they were kicked out of the country, back to pick beans or whatever. So after a month I again needed a place to live and people to hang out with. I still thought of myself as a dirt-bag artist type, so using Craigslist I found some dirt-bag artists in a bohemian neighborhood called The Plateau.

  Eric was a twenty-four year old visual arts student. He was a shorter guy, a hundred and twenty pounds with perpetually greasy, long blond hair. He loved to wear bright, tight, hipster clothing, paint weird paintings of spaceships, do drugs, drink, party, and fuck anything he could within reason. I liked him, even if I was slightly afraid of his self-destructive tendencies. I figured I could learn something about pickup from him. He could be my guide to the Montreal party scene.

  The first week we lived together, he snuck into my room, stole my pot, and replaced it with two unmarked pills.

  “Bro,” I said, annoyed. “You took my pot.”

  “Yeah man. We sort of have an open house like that. But I gave you some Ritalin.”

  “I don’t want Ritalin.”

  “No worries man. The house will get you back. We have an open policy like that.”

  Mark was a quiet, sad musician type. Tall and lanky, he smoked cigarettes constantly, pushing his long black hair back from his face in between puffs. He also loved cocaine, playing guitar, and listening to nineties music. I liked him too, even though he looked like a bum. He was intelligent, fun to talk to, and wanted to be a writer. His music was decent, his writing not so much.

  Lucy was a nice girl, about twenty-five, smart and well spoken. She was always available to chat, though I rarely cared to. She had huge tits and they made me somewhat uncomfortable, because she was my roommate and you don’t bang your roommates… you bang their friends. She also had a significant drinking problem. I could tell because she loved red wine, and whenever her mouth was red I knew she’d been drinking, which was often. She would later think I was a creepy douche bag, but in the beginning we were fine.

  They say you’re the sum of your closest friends.

  Eric told me his favorite pickup bar was Tokyo. “Easy hipster chicks,” he said. So I wanted to check it out. One night I walked up the stairs, past seven or eight pretty girls, but didn’t/couldn’t/wouldn’t open any. I cruised into the main lounge and stood near the dance floor, tapping my foot, bobbing my head and scanning like a Terminator for the safest option: someone easy, happy, alone, inviting.

  Many cool heads turned to check me out; I felt naked and out of my place. They were bridge-trolls, scarecrows, gargoyles. Three men huddled around every girl, all in sleeveless neon shirts and sockless, canvass shoes. They were all younger than me; I felt like an old man. They’ll be changing my diapers soon enough.

  I was wearing cheap, baggy jeans, a plaid shirt and generic Adidas shoes. I was straight up no-style. I didn’t recognize the music, or fit into the culture. It was isolating. My mind was racing with the eternal chatter—that little voice that tells you little lies, “Go home, you aren’t cut out for this,” and whatnot.

  At this point I had no concept of The Now, or Ego, or any of that stuff. The puas just told you to approach within three seconds, before you could think. But here I was, head i
n the sand, stifled in my skull, heart palpations, etc. The same old bullshit that every new guy goes through, before they repatriate themselves to the realm of men.

  You’re supposed to be seen with girls, so that other girls think you’re pre-selected, thus making you appear Alpha: Ancient ape theory. I was pre-selecting which toilet to throw up in, completely aware that I was a loser alone, not talking to girls—a self-conscious, poorly dressed guy with weird social anxiety issues in a strange city far from home. I got a beer, and then another, and felt quite naked drinking alone. All I had to do was say something, anything, to somebody.

  I slinked through the club, and was bumped around by the cruel dance floor before I made my way onto the terrace; it was packed with handsome hipsters—an ocean of American Apparel outfits under perfectly coifed hair, drinking Pabst beneath Chinese lamps.

  Focus Sebastian.

  I spotted three hotties, and tried to move, but my legs were frozen—I couldn’t do it. The girls sensed my fear vibrations with their pussy-powers, and their eyes grew wide, pupils probably dilating too.

  What do you say? Are those their boyfriends? What if they ask where your friends are?

  The chatter grew in intensity and I started to justify doing nothing.

  You don’t want to interrupt their conversation, they’re with their friends. Don’t creep them out. You can try again tomorrow.

  I pulled out my cell phone and fucking pretended to talk to someone. I actually mimed talking. Pathetic. Thank god for my cell phone; my water-wings, my savior. I’m not alone…I have friends on the way! I’m just on the phone, waiting. Don’t look at me you handsome bastards. And people did look at me, but they weren’t looking at me—they were looking through me, into the ether, too wrapped in their own thoughts of work, sex, money, school. Y’know, human shit.

  I hung up on my imaginary friends and walked briskly off the terrace, past the bar, through the dance floor, down the stairs and out of the club. I hopped onto my bike and peddled home at a slow pace feeling like the lowly, pathetic, beta male that I was. Lame, lame, lame.

  I lay in bed that night looking out over the cool Montreal rooftops, thinking about life and the girl I left behind. I vowed I would never, ever, go out to approach girls and not even try, at least once. I’d come too far, and given up too much to be that guy. No, not that guy; I’m going to be awesome.

  Chapter 7

  Rooftop Combat

  (Mario is a Cock-block, Wario is misunderstood, the Princess is overrated)

  The majority of the Anglos (foreigners, Farang) worked in call centers… so I found work in a call center. It was bullshit slavery, as all jobs seem to be…but at least I could practice my verbal game by selling crap to strangers. And lots of young girls, on break from university, worked there. After the day was over I would ride my bike home, power nap, watch pickup dvd’s and then go out. I was on day twenty-seven straight of going out and still hadn’t picked up a girl.

  Eric had become my de-facto wingman. He was more into getting fucked up that picking up girls, but he was smart and full of conspiracy theories about corporate agendas, which was entertaining.

  “They control the food, the banks, the media,” he told me, while sucking back a cup of Asian msg-noodles.

  It was all interesting but I didn’t see how this knowledge would help me get laid. I’d already been through my punk rock-angst stage, but I humored him. He also taught me how to find free vegetables in dumpsters, how to sneak into movies via back doors, and how to scam booze at the bar by stealing pitchers when people weren’t looking. This all helped, since I was broke. It’s amazing how easy it is to get by on nothing in Canada.

  Montreal has flat roofs and if it’s warm, there’s always a rooftop party. One humid night he took me to one. I patrolled around scouting chicks, trying my best to be charming and doing alright. Most of the pretty girls found me amusing but weren’t feeling the love. My hair was shaved short and I felt scary looking. Eric called me, “Sebastian the Skinhead.” I knew the girls would feel whatever I felt and I didn’t feel good. I had far too much trepidation. Nothing a half a dozen beer couldn’t fix. I finally got a solid buzz on and met a cute girl that was willing to listen to my odd questions like, “Who would win in a fight, two hundred midgets with pitchforks and body armor, or one T-Rex?”

  “Oh, definitely the T-Rex, he would stomp them.”

  “Au contraire!” I replied. “Midgets though small, are very strong. They could run up his tail and gouge the Rex’s eyes out.”

  “No. The T-Rex is huge. It would win.”

  “You’re not my dad.”

  “What?”

  Out of the corner of my eye, I spotted a commotion. I looked over and Eric was arguing with some tall lanky scenester guy. This dude was pushing his finger into Eric’s chest and spitting into his face, “Where’s my money, you shit!?”

  “I don’t have it.”

  “Give it to me, you shit.”

  “Dude, I said I’m broke!”

  I’ve got issues with bullies. Actually, I was craving combat. Nearly a month of hitting on girls and not getting laid, my over-abundance of testosterone boiled my blood. I finished my beer and marched over, mentally preparing for battle. I didn’t know yet that Eric was a brutal drug fiend and this guy was his junkie wingman. I approached the tall guy.

  “Hey, I think you should lay off,“ I said.

  He looked at me, then at Eric, then at me, took a drag from his cigarette, and walked away.

  Yeah, you’re a tough guy.

  So I went back to talking with girls. I was doing pretty well too. Most of them were nice to me now, some very cute ones too. I asked one for her number and I got it. I was getting really proficient at collecting phone numbers and Facebook addresses, even though almost all of them were fakes, or they didn’t answer or text back. As I was punching one into my phone, I noticed Eric and the lanky dude near the end of the rooftop, within a cloud of dust from their scuffling. Lanky guy had Eric in a headlock and was getting ready to feed him shots with his fists.

  “Fuck this guy,” I said to a girl, shoving the phone into my pocket.

  Sebastian of old would have watched from a distance, but Sebastian the pua warrior started a slow, semi-drunken jog, fully committed to kicking this guy’s ass.

  Full intent, full belief. Go bro. Everyone’s watching.

  From about twenty feet away I yelled, “Hey fucker!”

  He released Eric’s head and looked up in time to take my body slam. His knees were at the same height as a low ledge, so he flew head over heels, like a spinning rag doll, off the roof only four feet down, but onto his head. His face slid across the gravel and he laid there motionless until the dust settled.

  Silence.

  A gasp, and then another.

  Someone lit a joint.

  A few people laughed and, omg’d.

  I thought I’d killed him.

  So that was my fate… I’d be a prison bitch. My sphincter would be destroyed and I’d trade cigarettes for favor and ferry parcels between gangs. I’d have to join the Arians for protection. Do they need writers in jail?

  And then gopher like, he popped up, stabilized, and swept the dirt from his face with his skinny arms.

  “Heeeey maan, that wasn’t cool!” he said.

  Then he pulled a package of smokes from his shorts, removed a green lighter from the pack, lit one, climbed the ladder and walked back to the party.

  The music started up and they all went back to the same.

  These people are… something is wrong with them.

  I didn’t know yet, but many of Eric’s friends were junkies-in-training. They were just so clean and young. But like experienced child soldiers, you could see it in their bovine drug eyes.

  I’d never smashed someone before, and I felt guilty. Is this what warriors feel like after they’ve slaughtered their enemies? Adrenaline, pride, and shame?

  You’re very enigmatic.

  “Hey bro, I�
�m going home,” I said to Eric.

  “Sure man. Whatevs,” he said, and then he walked over and hugged the lanky guy.

  What the hell?

  I felt sad like I’d never comprehend the human condition. I climbed down the ladder and left the party without saying goodbye. Very childish of me, I know.

  As I pedaled my way home past the bagel shops, cute little parks and cafés and bars, I looked back towards the roof-party, and laughed.

  Chapter 8

  Misandry (Epic fails)

  I stood on the pavement, outside the shitty club, and every critical rejection hit me, chopped a piece out, and knocked me down. But this was a good experience—the worst of it. Every fighter needs to have his ass kicked a few times to toughen up.

  “Get away from us, hairy chest man!” The drunk nineteen year old girl yelled.

  “Yeah!” Hairy chest man!” Her friend frothed.

  “Button your shirt, hairy chest man! You’re ugly!” The third chimed in.

  And all this hate, simply because I made a joke about Jessica Alba having sex with dolphins. It was an article I’d read that day in the paper. I merely suggested that animals might make better lovers than men under certain circumstances, and perhaps she had enjoyed it. It wasn’t meant as a provocation, but some bitches be lookin for a fight. Sometimes they just freak out because they’re either a. stupid, b. drunk, c. crazy, or any combination thereof. Throw in the occasional lesbian, feminist studies major, or misandrist man hater—it’s dangerous out there.