A Thousand Tiny Failures : Memoirs of a Pickup Artist

by Tony D

  “Sebastian, this is Christian,” she said, holding onto his bicep with both hands. She had an apologetic expression. I’ve always been intuitive—it’s a Piscean trait. I had a feeling they’d banged before and were considering hooking up again. Fuck that. I’ve lost out to good looking guys far too many times. I’m the new Sebastian. I win.

  “Hey man,” he said, shaking my hand.

  “Hi there,” I replied. And there was this awkward moment. I mean, who’s banging Sarah tonight buddy? You’re not prepared. You haven’t read The Art of War, or The Prince, or The Art of Seduction. You haven’t been yelled at, threatened, ridiculed by hundreds of women. You haven’t traveled across the country to learn how to pickup girls and spend seven days and nights a week for five months doing so.

  We all sat down, and he leaned into her, not away like I did. He was working hard to keep her attention. I gazed around the room—everywhere but at Sarah. I wouldn’t play the eager-man game. I kept a slight smile on my face to appear carefree and happy. His desire was transparent. They talked about people they both knew and things they’d done together. Then he got up and went to the bathroom.

  “We have a history,” Sarah told me.

  “I can tell.”

  “Sorry.”

  “No worries.”

  I was getting a little worried, but I wouldn’t allow myself to fall into a scarcity mindset. It would manifest itself in my words and actions. He came back and sat with us, again ignoring me and talking to her. He mentioned something about her shoes and how much he liked them.

  “Oh those ugly things?” I said, glancing at her chucks. “I told her to dress down tonight so people wouldn’t think she was a prostitute.”

  She glared at me, but with a coy grin. His eyes got big and there was a moment between us men—an eternity in a second—like when two great beasts lock horns and the smaller of the two projects defeat. I have you now you bastard, you tall, good looking, skinny jean, put a bird on it motherfucker. This is for all the girls you banged with the cocaine in your pocket, by the shitty Arcade Fire rip-off band you play in, and the feminist study groups you attend on Thursdays only because you think it will get you ass.

  “I like your shoes too man,” he said, referring to my cheap Aldo specials.

  “Thanks!” I said, and reached over to give him a high five—trying my best to appear civil.

  He started talking to her again. “So what happened last week? I lost you at Chris’s gig.”

  I interrupted. “She was kidnapped by a man on stilts. He had a big dick; it needed its own stilt. A dick stilt. A, Dilt. She spent the night aligning his chakras and smoking opium.”

  “Totally! It was amazing,” she said, kicking my leg under the table.

  Christian looked at us and frowned. “Oh, I’m sure she’s not that type of girl.”

  “Sure she is, aren’t you?” I asked her.

  “Yeah. I’m just a total slut.”

  After a few more minutes of this horrible banter he got up to answer his cell phone.

  I said to Sarah, “Hey, wanna get out of here?”

  She looked over at him, then at me, “Umm, well, let me just go and talk to him first.”

  “Oh ok,” I said, smiling. “Well, I’m going to start walking east on St. Denis, and if you say goodbye to him quickly, you can catch me before I’m gone.”

  I got up slowly, held her eyes for a few seconds, then turned and started walking towards the door. I didn’t look back. I had to believe in myself. I got to the stairs and went down the spiral, past some kids sniffing things and drinking things, until I reached the ground floor exit. I stepped out onto the pavement and moved forward at a decent pace with the sound of bass fading with the distance. It was a nice night. I wouldn’t mind walking home. I heard the door open and slam behind me, then the pitter patter of little feet on the sidewalk.

  “Hey!” Sarah yelled.

  I didn’t look at her until she caught up.

  “Well hello there, m’lady.”

  We walked for a minute in silence until she said, “Were you really going to leave me there?”

  I let it hang while I thought out my answer.

  “Nah. I don’t think so, maybe.”

  “You would have?”

  “Nah.”

  “Ok then. You’re weird.”

  “Better than normal.”

  “I’m not so sure.”

  “Me neither,” I said.

  We got back to her place and into bed. We kissed a little but she shut down. “You can’t fuck me tonight,” she said. “I’m on my period.”

  “I don’t care. I’m a vampire.”

  “Not tonight, ok?”

  “Ok.”

  The pickup community calls this, “last minute resistance,” but I think she was just pissed off. They say you should get up, check your email or something. Do something to make her feel a sense of loss—but I didn’t care. I went to her bathroom and rubbed one out. As I drifted away into the void with one hand on her ass, I wondered if all this was worth it. I should probably be in university learning to be a doctor or lawyer or carpenter or something. Not a fucking pickup artist.

  Chapter 18

  Orgasms (Dream catchers)

  I went out every night, seven nights a week. I didn’t just want to practice pickup, I wanted to be great at it. Fuck mediocrity. I’d follow the usual routine of slaving at the Call Center of Doom, ride my bike home, smoke a bowl of Montreal weed and power nap, wake up, read pickup and self-help books, watch videos, then go out. I’d been on a handful of dates with some cool chicks, but nothing was panning out. Maybe I needed to work out more, or find a social circle, or meditate. I wasn’t sure when it would get easier, but I was definitely focused. I always believed it would pan out. I had to. I had to change my life.

  Most of the girls I met were between eighteen and twenty-three. They went to the clubs; they were the ones I couldn’t get in high school. I’d tasted success and I wanted more, so I kept up the regimen because it was working. I rarely stuttered or had panic attacks. I was funnier, more confident; I dressed better and had a small group of friends, mostly guys from the pickup lair, people I had approached and the social circles of various roommates. I was happier, much happier.

  Olivia found herself a real boyfriend, so we stopped hanging out. It was just like that. It ended. I wasn’t sad; it was more like I lost a cool pair of pants. I guess I’m a jerk. One day I got on Facebook and searched for Montana, the BJ cat girl that gave me a fake number. I found her and sent a poetic and heartfelt message about how I’d love to see her again. It was a little bit sappy, and the pickup guys would call it beta, but I had nothing to lose, and it worked because two days later she agreed to meet me for drinks.

  I arrived at eleven p.m.. The bar was dimly lit, with high tables and scattered couples sharing stories and drinking cocktails. Montana was already there, and when she stood up I kissed her on the cheeks, as is the custom in Quebec.

  “You look nice,” I said.

  “Thanks. I think I look like shit. I stayed out too late. How are you?”

  “Awesome. I’m living the dream.” I took a sip of my rye and ginger without lowering my eyes from hers.

  “The dream huh?”

  “Yeah, the dream.” I slapped her thigh lightly.

  She moved closer, so I put my arm around her shoulder. We were a match. We fit. It’s always best to assume you’ve already succeeded—that you’re the shit. Narcissism works.

  Atta boy, champ.

  She went to school at Concordia, studied a little bit of everything for no apparent reason. Her favorite things were long trips to faraway places where she could hula-hoop on beaches and surf. Pretty girls love beaches because they can practice their two favorite hobbies: being attractive and being comfortable.

  She was impressed how I picked her up, and she loved my fictional dirty talk. She called me, “Mr. Writer.” At one point, I put down my drink and kissed her, with tongue. I licked her s
traight teeth and she bit my lip. Her eyes got me. They were just so big and pretty.

  “You weren’t impressed enough to give me a real number,” I said.

  “I totally did.”

  “Nope. You changed the last digit.”

  “It was an accident. I promise.”

  I adjusted my crotch because my boner was in an awkward position. I think she noticed.

  “You owe me, bitch.”

  “Hey!” She pinched my stomach fat. “What do you write about anyway?”

  “Mostly about myself, people, odd situations, women.”

  “Really… so are you going to write about me?”

  “That depends.”

  “On what?”

  “We’ll see what I can learn from you, I guess.”

  She finished her drink. A few guys at another table were checking her out. She ignored them.

  “I’d like to read some of your stories,” she said. “I wrote a few short stories too, but they’re not very good.”

  “It takes practice.”

  “Yeah I know.”

  “So, what else do you do?” I asked.

  The server dropped off two more drinks. They were good and strong. We both took big sips.

  “I’m good at lots of stuff,” she said.

  “Like what?”

  “I make things, earrings, jewelry, dream-weavers.”

  “And sell them when you travel?”

  “Yeah. I sell them sometimes.”

  “Are you going to make me a dream-weaver?” I asked. “I have dreams.”

  She leaned back and sized me up. “I don’t know. I don’t really know you.”

  “Well, I put my dick inside you. You know me pretty well I’d say.”

  She laughed, squinting her big, pretty eyes. “That’s not knowing. That’s just a blow job.”

  “So get to know me better then.”

  “Ummm, nah. I just want to fuck you,” she said.

  Dude, dude, yes!

  I know, I know!

  This was the window, time to climb through before she changed her mind.

  “Let’s get out of here,” I said, looking at the time.

  “Ok, my place is a block away.”

  As we walked back to her apartment, I felt in my back pocket for my condoms. I’d only brought two. I kept my hand on her behind and played with it. The booze was in my blood and my dick was still hard. I stopped to kiss her on the doorstep and pressed it against her so she’d know I was ready. She reached down and gave it a squeeze. Good girl. No bullshit. We got inside and she went to the bathroom. I took of my shoes and jacket and explored her apartment. It was clean. Lots of books on her shelf, dream-weavers in her windows. It smelled like patchouli, she was a bit of a hippie. Montana came out and walked straight to me, kissed me on the mouth and played with my balls. Nineteen year old glory! She started walking backwards, slowly, towards her room and fell onto the bed, pulling me down with her. I sucked on her neck, I squeezed her thighs. She made little grateful noises and scratched lightly at my shirt, so I stood up and took it off.

  “Tell me another story Mr. Writer.”

  “About?”

  “I don’t know, you’re the writer.”

  She undressed until we were both in our underwear.

  “There once was a man who came out of the east,” I said, and licked from her belly button to her neck. She sighed. “He travelled the world seeking out adventure. His conquests of women became the stuff of legend.” I got on top of her and ground my crotch into hers. She let out an encouraging moan, her eyes widened. “One day he met an orphaned farmer girl. He promised her five shillings in exchange for a place to sleep, but she knew her father would refuse such a handsome man sleeping under his roof with his daughter.” I pulled out one of her breasts, squeezed it, and stuffed it in my mouth, licking all the way around her nipple. I reached down and felt her pussy; it was soaked through her panties. I leaned back and continued.

  “So that night she left her window ajar so the man could slip in when her father went to sleep.”

  “Did he come in?” she asked, between heavy breaths.

  “Of course, at one a.m., she heard him at the window and then felt him slip into her bed.”

  I pushed aside her panties and slipped two fingers inside of her. She moaned and bucked her hips. I flipped her over onto her stomach and kicked off my boxers. I kept one hand at work on her inner thigh and used the other to slip on my rubber. Practice makes perfect and I’d had lots of practice lately.

  “She didn’t think she would sleep with him,” I continued. “But his presence in her bed was too much for her, it made her pussy wet knowing that her father lay asleep, just down the hall.”

  Then I poked my thumb into her pussy, just a little, not enough.

  “Ask for it,” I commanded.

  “Yes!”

  “Louder.”

  “Oh please, I want it, I want it!”

  “What’s my name?”

  “Sebastian, I want it Sebastian.”

  “Beg me!” I slapped her on the ass.

  “Pleeeeease.”

  “I like it when you beg.”

  I slapped her ass again, pulled her head towards me and put my tongue in her mouth, pushed her face down into the pillow, and ground the tip of my cock around the outside of her pussy in little circles, only allowing the tip in, and then taking it away. She was soaked.

  “Please Sebastian.”

  “Please what?”

  “Please fuck me!”

  “So dirty and bad!”

  “I am,” she moaned.

  I flipped her back over so she could look me in the eyes.

  “You gave me a fake number. I don’t think you need this dick.”

  “Fuck you!” She laughed.

  I carried on with my story about the secret medieval affair, while I finger-banged her. She kicked her legs out play-violently at my chest. It was all part of the act. When she couldn’t take it anymore, I said, “And when the man sensed her moment of weakness, he pushed his dick into her!”

  She laughed just as I penetrated her. “Ohhh, mmm, haha.”

  “Shut up. I’m the writer,” I said, and pulled my fingers out. Then I spread her legs and pushed my cock deep inside and it was…

  The loosest pussy I’ve ever been in. It was like sticking a wiener into a deep bucket of pudding. I tried various angles of attack: low to high, left to right, ass up, ass down; all while reciting improv poetry. She went mental, but I had to focus on the various whimpers, cries, moans and other sensations because my safely wrapped dick couldn’t feel shit. The wonderful girl, she came three times. She was designed for orgasms. She had a big, fat, magical pussy. I popped once, like usual. She was so fun, even with her broken muffin she still got me off.

  And then I washed my dick. She walked into the kitchen and poured me a drink of water.

  “Sorry but you can’t stay over,” she said.

  “Oh. That’s ok.”

  “I have homework.”

  “Cool.”

  And then I went home and posted the story on the forums, for my legacy. They loved it as usual, the faceless, horny men of the Internet. I was a bit bummed she kicked me out. I wanted a girlfriend.

  Chapter 19

  “Good girl?” (Le Guerrier)

  Sarah texted me and wanted to go out again. I was pretty sure she’d be dtf this time if everything worked out. I thought I’d blown it with my walk out on our last date, but she liked me. She was sort of masculine. I’d been meeting lots of girls that acted masculine lately. It was like they wanted to be the leader. I don’t like that. I like being the man. The best women I ever dated were from Mexico, Brazil, and Columbia. They’re still girls. North Americans have it all backwards. It’s a role reversal.

  I’d been seeing Montana about twice a week, and the sex was great, but that’s all. We would fuck and then she’d kick me out. I’d never been with such an orgasmic girl. I could usually make her come thre
e or four times a session, but she didn’t want anything else to do with me. It was like, the closer I came to being awesome with women, the further I was. In my head, I wanted to be a player, but really, I wanted a girlfriend. My standards are just higher than my attractiveness. I’m like a cute puppy that you want to cuddle, but I smelled like puppy pee.

  I’d been reading two books called, A New Earth, and, The Power of Now, by Eckhart Tolle. Now, before going out I would meditate for half an hour to get in The Now. I loved losing myself within myself. It’s like that scene in Being John Malkovich, where he crawls through the portal leading inside his own head. That’s what I’d been doing my entire life; crawling around inside of my skull, lost, pursued by Minotaurs.

  Meditation is dope, but not as effective as cheap French beer. Practicing pickup seven nights a week was taking its toll. It makes you a little bit weird… no, a lot weird. I no longer saw people as people—just opportunities. I didn’t view women as women, but more like characters in a video game. Of course, it was different if they actually dated me, but I was frustrated from all the flaking. The only way to deal with the tremendous amount of rejection is to view the whole process as something separate from my reality, so it isn’t personal. As for approaching, it was really no big deal anymore. Just an action you take—something to do. Like making toast.

  I met her at her place. Sarah was in her bra and Mickey Mouse boxers with a French cigarette dangling from her thin lips. Her feet were on the coffee table and she was painting her toes pink. I love pretty feet, not sure why. Cute toes, they just look like smooth little sausages or something. I leaned over and pinched her foot.

  “Ow! No pinching, Sebastian.”

  “I want to bite them.”

  “What? Why?”

  “They’re too cute.”

  “You’re a weird guy.”

  “Yeah. I am.”

  She got dressed in a short white dress, and we left for a local bar to catch the first band. Sarah got a call so she stopped outside the bar to talk. I said I’d meet her inside. It was one of those hip French places and there were more pretty women than handsome men. It was some sort of feeding frenzy and I regretted being on a date in a venue with so many options. At one point, this little brunette cutie walked up and said something in French.