A Thousand Tiny Failures : Memoirs of a Pickup Artist

by Tony D

  “Really? I don’t think so,” he said. “This is art.” He picked up his acoustic guitar and started plucking.

  I hesitated before speaking again, picking up the bong and taking a long hit.

  “Art is expression of soul, “I said as I coughed. “It’s creating something great out of something simple. You’re blowing it with these women. You don’t even see it. What I’m saying is you’re putting the girls on a pedestal. You need to be more teasing, more abundant. You need to be more of an uncaring asshole. Like, making that girl dinner and putting it on the roof? It’s so, needy. Don’t aim to please her just because she’s a woman. Make her earn that shit, like you would any potential friend. All you had to do was go for a walk, have a drink in one of the awesome local bars. You don’t even have to pay. Tease her a bit, make her work for your affections.”

  He looked up, one eye poking out from behind his grunge hair. “I don’t want to be like that. I like the way I am.”

  “Then you’ll keep getting what you’ve always gotten.”

  He strummed his guitar and took a drag from his cigarette.

  “I just don’t want to be like that,” he repeated.

  Fuck this guy bro. Go be productive.

  “Be like that? Be like what… confident? Charming? Do you like not getting laid? You enjoy being rejected?”

  “It’s not like that,” he said. “I just haven’t met the right one. It’s not all about sex, Sebastian. You need to relax.”

  “Mark, you haven’t been inside a vagina in four years. Things need to change.”

  He stood up and slammed down his guitar, making the strings buzz. “Shut up, shut up, shut the fuck up with this pickup bullshit Sebastian!”

  We sat in silence until he reached down and picked up the bong, took a toke, and passed it to me. “Yeah, I suppose I need some help. I still think Mystery is a creep. Hey, wanna jam? Go get your guitar.”

  I didn’t want to jam. I used to be like Mark. I can’t say I’m better than him, even though I was more confident with women. Hell, if it wasn’t for pickup I wouldn’t even be in Montreal. I’d still be living with the stoners in Vancouver, doing nothing, rotting in depression the way Mark was now. I definitely wouldn’t have slept with all of these pretty girls. I’d probably have shot myself by now.

  I went back to my room and checked the forums. I was gaining small fame amongst newbies, and respect amongst veterans. I liked to write weird, poetic stories about my adventures and they seemed to inspire. Sometimes I would get like fifty replies to my articles. Guys were telling me I was a great writer, a genius, and asking if I would write a book. I felt like I was living a choose-your-own-adventure novel, and I chose to hit on chicks. The field reports were my way of rooster cawing. I just wish I could find attention like this from girls instead of pickup dudes.

  One night, I came out of my room and Lucy was making some food in the kitchen. I crept up behind her and said, “Boo!”

  She screamed and yelled, “Fuck off Sebastian, you fucking creep!” And then ran, pitter, patter, crying, to her room. I stood there in shock. I’d never had issues with Lucy before. We had some interesting chats but I never hit on her. I followed her down the hall and knocked on her door.

  “Are you ok? I, umm, didn’t mean to scare you.”

  “Go away,” she belted from behind the door.

  I stood back for a second before deciding to continue.

  “What’s wrong?” I said.

  “Look, I just don’t like you… ok?”

  “Why?”

  She didn’t answer right away. I heard some rustling of papers, and then a silence.

  “Look, I just think you’re a douche-bag. Don’t take it personally.”

  “Wait,” I said, resting my head on her door. “How can I not take that personally? Lucy? Open the door and talk to me.”

  Silence. More rustling. My churning gut.

  “Fine then,” I continued. “I’m moving out. I don’t want to live somewhere I’m not wanted.”

  That’ll learn her.

  She thinks I’m Ted Bundy. She thinks I eat babies. I went back to my room, fell onto my bed and sulked. I wondered what she could be freaked about. Then it hit me: Mark, that pussy ass bitch, snitched on me. And then there was the time at her party when I was hitting on her friends. I said some pretty weird stuff about prison rape in pop culture. I couldn’t stop the chatter so I got up and wrote her a Facebook message.

  “Lucy. I know you think I’m a creep, but one day I’m going to help men around the world improve their self-esteem. I hope we can be cool. I’m giving my two week notice. Sebastian.”

  I hit send. And then I regretted hitting send. And then I came to peace with my decision. No, I didn’t. And this thought process went on into the quiet night until I smoked a joint and finally passed out.

  The days went by, and Lucy wouldn’t even look at me. She would get home from work, rush to her room and shut the door. Once I caught her in the kitchen and tried to confront her, but she just walked away, shooting me a bitchy look before slamming her door. I found out that both Mark, and Eric, had been talking shit about me. Everyone in their social circle knew I was studying to be a pua and since I worked with Mark, that meant everyone at work knew too. Fuck my life. I didn’t even want to be a man whore; I just wanted a pretty girlfriend that liked video games, deep books, self-help and sex. Well, maybe two pretty girlfriends. And they would share me—except when I went go on book tours which would be, “free time.”

  Every day at work we changed seats so we’d be forced to socialize with the other slaves. It was designed so that we would never fit in, or get too comfortable. This week, Mark’s favorite gossip topic was the weirdo roommate who was obsessed with reading Machiavellian books about picking up girls. However, there was an amusing side effect; I noticed the girls at work were checking me out and hovering around my station. Some of the guys even asked me for dating advice. He wanted to alienate me, but instead created intrigue. Any press is good press—thanks bro. It was nice living with you, but I don’t fit in with the insecure anymore, or so I told myself. But still, after all this I would hang out with Mark and act like he wasn’t a total shit-talking, cokehead beta male. I suppose I’m worse since I’m tattling on him to everyone that will read this book. It’s really hard to make good friends. I don’t trust many people.

  I came home one day to Eric’s intervention. There was a gay looking little hipster kid crying in the living room, flanked by two fat girls latched onto his arms. They were staring at Eric who was sitting on the living room floor in a poncho and pink sweat pants.

  “Eric,” sniff, “we, care for you!” He said. “You’re killing yourself.”

  Eric just stared at them, arms crossed. “Bro, I don’t even know you. We’ve hung out, like five times.”

  “What are you talking about!? You know me soooo well!”

  “Yeah, whatever. Piss off,” Eric said.

  The girls all cooed, “Eric listen to him! We want to help you. You party too much!”

  I went to my room and shut the door. That could be me in a few years, because I party too much. I checked my online dating profile. I had zero messages which was surprising since the previous evening I sent out twenty-seven messages. Apparently online dating wasn’t for me. I could hear one of the girls crying, and Eric telling them to, “Go the fuck home,” which they did shortly after. Good for him. Even though the guy was a total fuckup, I respected his devotion to debauchery and blatant disrespect for authority; both of which are great assets for aspiring racontours.

  Since I moved to Montreal I’d lost fifteen pounds. I was biking to and from work five days a week and watching my calories, eating soup instead of sandwiches, and jogging. It showed in my face, my waist, and my game. Women were definitely more receptive when I looked fit and healthy. I grew my beard out to appear more masculine. I also bought skinny jeans, high-top runners, a v-neck and styled my hair. I caught myself in a store window: I was a hipster
.

  My two week notice arrived and I moved away from Lucy into a new apartment with a weird dude that never left his room, and a Spanish kid that couldn’t speak English. My bedroom was a tiny shack stuffed in the back of a dirty, dark, crooked hallway. The place also smelled moldy, like bubonic plague. Not exactly a pimp shack, but it was all I could find on short notice.

  Olivia was back from her trip and I waited to meet at her apartment. We only saw each other about four times in the previous month, so our relationship was light. She rode up on her new red bike with that sexy body moving back and forth, back and forth, like a pretty bell. I liked her, but I’d found my interest waning. She’d cut herself along her arms, as if with a razor.

  “Did you do that because of a boy?” I asked.

  “Yeah.” Her face turned red. “I was on shrooms.”

  “And you cut yourself because of a boy…”

  “Yeah.”

  “He’s not worth it. No guy is. Don’t fuck up your beautiful skin over some douche bag. You’re going to meet plenty of douche bags.”

  “I know.”

  She wanted to hang out often, but I’d rather be out meeting new girls. It was a sickness. Looking back, she was more interesting than most. Now that she’s older, I bet we would be great together. She was into music, but when I tried to talk about anything bigger, more philosophical, she’d just blink her eyes and laugh, tell me how interesting it was, and move on. She let me hypnotize her a few times which was fun, and fucking her was glorious. Her body was a carnival. But she was a kid—and so was I, sort of. Many westerners seem to stay children. Why should we grow up? If we need money, we get a job, or go to welfare. If we need food, we buy it. The only problem is as we age we look different. Our skin sags and puffs and wrinkles form, and hair falls out, and vanity fails us. Then even though we look old, we still feel like children. This is what happens to those who never experience hardship or pain or develop self-esteem based on anything other than their good-looks. Certain tribes send their children into the forest to learn survival skills. When they return, they’re deemed men. In North America, we play Call of Duty.

  We locked up our bikes and went inside. Her roommates were in the living room, so we went to hers. We had to lean into the door with some force because something was holding it closed. I pushed it open for her and walked inside. Clothes were piled on top of books, on top of records, on top of dirty dishes, and shoes, and underwear, and newspapers. Her bed sheets were piled in the back corner under a pile of fashion magazines. There wasn’t a clean spot in the room. Even her bed was covered in miscellaneous make up kits, guitars, keyboard parts, vitamins. It was just like her last apartment, but worse. It was a fire hazard, or a scene from hoarders.

  “It’s a bit messy, oopsy!” she said.

  Damn. “Yeah, have you considered cleaning it?” I said dryly.

  “Yah, I should do that for seriously.”

  She’s eighteen, she’s scattered, she’s a slob. A really hot scattered slob. We cleared the bed and I made her put new sheets on. She played Bloc Party on her IPhone. I got her down on her back and really gave it to her, recently freed convict style. After all, I didn’t know if I would ever sleep with an eighteen year old again. I didn’t get any in high school, and I wanted to make up for lost time. As we were fucking she said, “Choke me.”

  “What? Your neck?”

  “Yeah, here,” she said, motioning with her hand.

  “How hard?”

  “I dunno. I’ve never done it before. And slap me too.”

  “Ok,” I said. And I choked her a little, and I slapped her face a few times, very lightly.

  “Harder,” she said.

  “Ok, ok! Like this?” I slapped her face a bit harder.

  “Yes. Yes”

  “And like that? You like that? Are you my little slut?” I said as I smashed into her.

  “Yes I do! I am!”

  I pulled her hair hard as I rammed her doggy-style, slapping her ass until the cheeks were pink. I bit her neck, I pinched her nipples just a little too hard, I talked dirty to her about how I owned her little pussy. She loved it. It was great fun. I went all Fifty Shades of Sebastian on her ass. That was the first time a girl asked me to dominate her. Now I always throw some nasty games into my sex. Just a little bit.

  Afterwards we were lying on our backs smoking a joint, and she said, “I haven’t heard from you in a week. What do you do all the time?”

  “I’ve been working all day and going out all night.”

  “Why go out all night. You know, I really like you. I missed you.”

  “I missed you too.”

  “You missed my body.”

  She bit her lip and looked at me, then out the window.

  “Olivia, I have to tell you.”

  “Yeah,” she said, still looking away.

  “I didn’t come to Montreal to find a girlfriend.”

  “Yeah,” she said.

  “I left one in Vancouver.”

  “Oh.”

  She was stifling her tears. I felt like a real bastard. Like a dirty fucking player. There was no connection. I needed a girl that was on my level, wherever that was, and this girl wasn’t. Not yet anyway. She was cute and eager, but that wasn’t enough for me. I’m pretty sure most girls act less intelligent than they are. They don’t want to seem smarter than their men, because most men are idiots. But shit, I didn’t know anything when I was eighteen either. I still don’t know anything except that there’s lots I don’t know-that I don’t know.

  “Hey, we can still hang out. Just don’t expect me to be boyfriend material right now,” I said.

  You’re a fucker.

  “I wish I wouldn’t go with every boy that asks me to come with him.”

  You’re a real bastard.

  “Yeah, me neither. Don’t do that,” I said.

  There’s no such thing as no strings attached sex. Every conquest leaves a little emotional trail that follows you like a wounded puppy. You’ll look back at times and see its hopeful, sad face, and go, “Awwww.” And then you’ll feel sort of bad. If you can’t deal with that, then you aren’t cut out for this. Some people say love is nothing more than a chemical reaction designed for pair bonding. I had no idea. I just knew this wasn’t the girl, and I needed to try more. Many more.

  “Come here,” I said, pulling her naked body towards me, and turning up the music.

  Chapter 17

  Sarah (The walk-away)

  I met her on the street, on my way home at three a.m. from a good party near St. Viateur St. I think I was introduced by someone, but didn’t notice her until she was suddenly on my left flank, looking up with big half-moon eyes, and then our arms suddenly brushing against each other. I’d been targeted. She was short, decent breasts, ok legs, but a great face. She would make a nice Victorian era painting.

  “Hi,” I said.

  “Hi,” she replied, stroking her hair over her shoulder. “What’s your name?”

  “I’m Sebastian,” I looked her up and down, slowly. “Who the hell are you?”

  “I’m Sarah!”

  “Were you at the party I was at? I didn’t see you,” I asked.

  “I was there, but I was hiding from you,” she said, batting her eyes coquettishly.

  “Why were you hiding?”

  “Because, I wanted to hide,” she said, and punched me in the arm.

  “Yeah,” I said, “because you like me. Here, pull my finger.”

  She laughed. “What no way! I’m not pulling that. Anna this guy wants me to pull his finger!”

  “Do it, dooooo it,” Anna said.

  Anna was walking with another random guy, who was doing a good job keeping her entertained, so I could work on my girl.

  “Bagels. Let’s get bagels!” Sarah exclaimed.

  We went into the bagel shop, one of hundreds scattered around Montreal. They stay open all night and fill up with party kids looking for three a.m. carbs. We stuffed our faces and I got
Sarah’s phone number. She seemed pretty down, but I was exhausted from drinking and hitting on unreceptive women all night. Now that I found one all I wanted to do was go to bed. Pickup can be emotionally, intellectually, and physically exhausting.

  I texted Sarah the next night and she invited me to a loft party in Mile End. I took the metro then walked to her house. I heard women giggling on the other side. She opened the door and was much prettier than I remembered. Her dark hair was hanging naturally, with just slight curls near the end. She had a little pink flower braided in just above her left ear. She wore blue jeans and her complexion wasn’t perfect, but I didn’t mind because she had a big, round butt. She was also twenty six, which was cool.

  “Hey, I’ll just be a minute. Here have some wine,” she said, shoving the bottle at me. Then she disappeared into the bathroom. Anna walked in wearing yoga shorts and a tank top. “Hey bud,” she said.

  “What’s up Anna? You going out tonight? Nice outfit.”

  “Oh this old thing?” she said with a laugh.

  She paraded back and forth across the living room, putting on a show, swinging her hips, sticking it out while she sorted through her record collection. I consider taking her right there, for a quick one before Sarah came back—but I wasn’t that gangsta. Women always do this; they have no interest in you until your dick gets near their friend, then the female competition gene kicks in. They have no honor. I don’t blame them. They need a winner to protect them from Saber Tooth Tigers, and rogue Neanderthal rape gangs.

  The party wasn’t far and the night was warm so we walked. Sarah laughed at all my stupid jokes like, “What would you rather sleep with George Bush for one million dollars, or Johnny Depp for free?”

  “Duh, Johnny Depp.”

  We arrived at the party; a sprawling warehouse transformed into a club with pounding trance and dub-whatever. There were a few pretty girls in their scenester uniforms and their beta-male counterparts with their neatly coiffed hair and elf shoes. I had to suppress my now ingrained addiction of relentlessly approaching every girl in the room. Today I arrived with one, and when I saw her talking and hugging some tallish hipster dude I had my regrets about coming into her world. It’s always better to bring a girl into your world, where you know people and she’s off balance.