A Thousand Tiny Failures : Memoirs of a Pickup Artist (14 page)

I’d heard that fame is a double edged sword. Many an insecure author had drank and doped themselves to death at the fists of fame. Here was a guy doing something deep, while I pursued women for the sake of validation. Maybe all art is porn. I decided when I was done with this
pua
crap I’d return to being an artist. I finished my poem. A pretty girl stood at the intersection waiting to cross into the book store. I gathered my things and started walking that way.

Blowjobs and Validation (The wonder years)

“Hey, I need to buy some swim trunks,” I told
Carly
. “Let’s go to
Walmart
.”

I took her to the home décor department and threw her onto the bed. Then I got on and started jumping on it. I was going to give her the best date of her life, without spending a dollar.

“Look honey, this is perfect for our mansion!” I said, holding a duck-head toilet scrub.

“Of course
daaarling
,” she said, playing along.

We went to the toy department and I chased her around, firing Nerf darts at her bum. Then we went to the clothing department and I put on a giant Teenage Mutant Ninja Turtles shirt and pretended to be retarded.

“
Carly
I like
yur
hair, it’s real
purty
n smells like baby dinosaur farts.”

This made me laugh but sort of
weirded
her out, so I dropped it.

I liked
Carly
. She was very feminine and just slightly submissive. She never gave me any feminist crap when I said things like, “Bitch, shut up and kiss me!” If I can call a girl a filthy slut and she laughs, she’s a keeper.

We drove up to the local lookout spot, got out and cooed over the sparkling city. I sat her on a bench and we started kissing. She let me feel her little boobs. I liked that she was acting confident, but I knew she was a
newb
at all this. It was romantic, with the city lights and crickets and all, so I put her hand on my dick. She played with it through my pants but wasn’t taking initiative, so I stood up and pulled it out for her. She tried to give me a hand-job but just tugged on it like she was trying to plunge a toilet.

“Ouch! No, no. You gotta work the outside, don’t squeeze so hard. Have you done this before?”

“Yeah. I know how,” she said. Her face was very red in contrast to her very blond hair and freckles.

She tried again more gently this time and was getting it right.

“That’s nice, but it’s too dry,” I said. She stared at it for a moment as if deciding, then put one hand on and swallowed it. I felt like howling at the moon. It’s a fantastic sensation whenever you enter a woman’s mouth. It’s like you just slaughtered an immortal, or landed on the moon, or conquered a small country. She was horrible at it. After a few minutes I stopped her. Then we looked out from the mountain, over the hills and beaches and we cuddled. Was this joy, or part of the eternal recurrence, a repetition of the inevitable? How terrible would the end of this story be?

I drove her home and her mother was in the window. “What would she think about you dating a thirty year old man?” I asked.

“Oh, she doesn’t care. She married my dad when she was nineteen. He was thirty-four.”

“Where is he now?”

“They divorced when I was ten.”

“Oh.”

I kissed her goodbye and drove home through the winding hills past cherry, grape, apple and pear orchards. I think I saw two deer fucking, their eyes startled and glowing from my headlights. I drank a glass of wine and passed out on my mother’s couch, satisfied that I was leading an interesting life full of adventure and romance.

That night I had a dream. There was a dragon all blue and red and smoking, one of those Asian types, with a pair of red lips and enormous dragon breasts. It chased me through an all-pink night club. There were only women in the club and they cheered and spit at me, as I sprinted for my life. I woke up startled to G.W. Bush giving a speech on the
tv
to a cheering crowd, something about bombs, and unity. I turned it off and went to my tent.

Number Three (You’re only as old as you lie)

I met Dianna at
seven p.m.
, at the beach. The sun was still high. She was wearing a blue dress that showed off her legs and boobs, which were substantially awesome. We bought some fruit coolers and found a spot on the grass near the water. She was studying to be a massage therapist, so I got her to rub my shoulders. “Oh yeah, Jesus, oh lord, right there girl, that’s right, ouch! Shit! Who taught you that one? Don’t do that again. Go back to how you did it before
dammit
.
Yeeesssssss
,
aaawwww
yyeeeaaah
like that! Damn. Don’t do what you did before, fire your teacher, keep doing this. Follow your instincts Dianna.”

“How old are you?” she asked.

“Me? Guess.”

“Twenty-three?”

“That’s a good guess!” I said.

“You’re twenty-three?”

“No. It’s just a good guess.”

“How old are you really?”

“I’m thirty.”

“Oh my god, you’re ten years older than me?” She said, leaning back.

I’d come to expect this from girls. Some don’t care, others make a big deal. It’s all the same to me. But I still prefer not to lie.

“Look. I don’t need to hear about your problems,” I said.

“Ha
ha
. No, you’re way too old for me but, you look so young!”

“Don’t hate me because I’m beautiful.”

“But,” she regarded me, “I shouldn’t date a guy your age. You’re old!”

“Don’t be racist.”

“What!? That’s not racist.”

I pulled her down, onto the grass, leaned in and tried and kiss her but she turned her cheek. I expected that. They always seem to do that the first time. It’s like they need to consider it for a few minutes.

“No seriously. I like you but we’re not hooking up. You’re thirty!”

“I don’t call you names,” I replied.

This went on for a few more minutes. I had a hard time keeping my cool. Why does one young girl not care and the other makes a big deal out of it? What’s the difference? We’re all going to get old, we’re all worm food, we’re all just waiting for the next
Chernobyl
, tsunami, or plague. The way I see it, at twenty you’re old enough to join the army and clear land mines. It’s not like I was sixty. My skin’s not droopy. Just because I’m into Transformers and she’s into Pokemon.

“Don’t you love the way the sky looks when the sun is dipping just below the horizon?” I said, again changing the subject. “It just makes you want to, I
dunno
, make out!” I leaned in to kiss her again, and this time she almost let me. I dropped a few on her lips and poked my tongue out, but I was denied entry. It just pressed up on her lips. I didn’t like where this was going. I’m not used to it. I finished my cooler, tossed it onto the grass and opened two more. “Hurry up and drink,” I told her.

“What are you trying to get me drunk so I’ll make out with you?” she asked suspiciously.

“You look thirsty,” I said.

I wanted her to get a little drunk, loosen the little moron up. Why do women do this? Why can’t they just relax? Do I need to meet her parents before she’ll spread her thighs? I was starting to miss the loose French culture. I took out my camera and snapped few pictures of us. She cuddled in and smiled. Pretty girls can’t resist a camera…vanity. If she wouldn’t sleep with me at least I’d have her picture to
wank
to.

This dance carried on for another half an hour. I tried again and again, with a masked aloofness. I invited her to my place but she had to get home, “Early day tomorrow, blah, blah, blah.”

She told me again that I’m too old. I wanted to tell her yesterday that I was getting blown on a hilltop by a girl younger, prettier, and smarter than her. I wanted to explain that I didn’t experience younger women when I was a young man and now I’m making up for lost time, but I didn’t. Instead I said goodbye, drove home, hugged my mom, and my sisters, watched an episode of Lost, wrote a poem, did some sit-ups, climbed in my tent and jerked off again.

It Hurts (Soul crushing)

Two down, one to go: It would have to be
Carly
, that pretty sunflower. I’d been in
Penticton
for three days, and in that time I had three dates. Not bad! In high school, I think I had three dates in three years. But even still, with all my experience and all those hours spent practicing pickup, I was being rejected. I was realizing that the pickup gurus were liars. Nobody is able to seduce supermodels with one hundred percent success. You can never attract every woman. And why would you want to? Where’s the fun in that? Maybe I should keep
Carly
, I thought. She was sweet, fit, smart, and beautiful. But I couldn’t stay in
Penticton
. There was nothing for me there. I would be bored. I needed to get back to
Vancouver
; to parties, music, art, culture, and city girls. I was just getting the hang of this pickup thing, and wanted to learn more. Maybe I was addicted? I couldn’t be a sex addict because I didn’t get laid that much. So I told myself I was addicted to growth.

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 was 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.