Lately this blog has gotten a bit preachy, and I don’t want that. To get things fun again, here’s a true story from the life of young Rob: an evening I met an experienced “wingman” off a pickup forum. I tried to capture the excitement and desperation of a “pickup newbie”. There may or may not be a morale at the end of this story—that’s up to you to decide. Enjoy, Rob

P.S. If you enjoyed this story, please pass it along to a friend or social media site. I’d really appreciate it!

I Once Met a Stranger Off the Internet and it Was a Horrible Life Decision

Getting good at meeting women was a skill I’d been desperate to learn. When I discovered “the pickup community” I found myself diving into its promises face-first. The deep end of obsession was where I landed. I left the dry comfort of normalcy to do things I’ll never forget—much as I wish I could.

The internet played a supporting role in my hilarious shame. It supported many of my bad decisions with corresponding consequences dripping in every shade of dreadful. The chilly evening I agreed to meet a man known to the internet as DatLadiezMan2 I met irony face-to-face, I shook his hand, and he said to call him Benjamin.

It was an accident. Arguably, an accident-waiting-to-happen. But undoubtedly an accident. For weeks I’d flirted with the idea. I’d created an account on the Venetusian Arts message board, reading its posts on picking up women with a wide set of eyes and a bloated heart. When someone chronicled the epic conquest of an “HB10,” I envisioned nothing less than the hottest girl my imagination could muster. I was in the exclusive company of pickup artists. It left me feeling both motivated and intimidated.

That’s why I’d approached the idea flirtatiously. I understood the only way to become “one of them” was through experience. Yet my experience up until that point was limited. The catch-22 grated me whenever I browsed the “Find a Wingman” section—which was daily, sometimes even hourly. I sifted through the posts with reverence, practically memorizing the messages that mentioned NYC. I’d drafted and discarded so many responses it was bordering on manic, or pathetic, or both.

Then, the day finally came. I did it. I responded. I discovered a post oozing with experience. It’s author was a man who’d unambiguously dubbed himself DatLadiezMan2. When I wrote the message and hit the send button, I was propelled to the edge of my seat. I boiled with anticipation.

With suspicious haste, a response came minutes later. It read:

Waz ur fone #?

In a flurry I typed out my number along with a superlative smiley face. My phone rang seconds later.

I understood the only way to become “one of them” was through experience. Yet my experience up until that point was limited.

I answered to a voice that immediately assured me he needed no help in attracting women—in fact, he was going to show me a thing or two, or ten. He cackled after saying this. I wasn’t sure if I should laugh or bask in silent gratitude. I was careful not to say anything that would betray my amateur status. I feared one slip might give DatLadiezMan2 reason to pass me over for another applicant wingman. I wanted him to show me a thing or two, or ten. I kept my mouth shut, limiting myself to niceties.

DatLadiezMan2, however, wanted to chat, wanted to bullshit, wanted to tell me his story about the time he had wild, unprotected sex. With an Upper West Side cougar. A married Upper West Side cougar. Fucked her. Raw. In her husband’s canopied bed. He said the incident had almost inspired an alternative to his DatLadiezMan2 alias. He’d considered calling himself The Cuckolder. Ultimately, he decided against it. He didn’t want to blow his cover.

My response: “Very cool.” I was playing it safe, not wanting to come off curt while also just wanting to lock-in plans. “So,” I continued, “How about we meet-“

“Woah!” He bellowed, “Hold it right there, rookie!” The way he said rookie oozed contempt. “If you liked that story, you’re gonna love this. It’s a little adventure I got myself into that I like the call, The Vacation Girls. If you thought The Cuckold was good, then The Vacation Girls will knock your condom off! Oh wait, my condom is always knocked off!”

The joke made no sense. I laughed anyway. More than laughed—I cackled and hooted. It was all done in the hope we could just set a time and a place to meet. I wanted tutelage, not The Vacation Girls.

But The Vacation Girls was what I got. Forgive me for misplacing the sordid details, my attention was compromised. I was nervous and trying to time my chuckles and attentive “WOW”s to the appropriate cues. The story was longwinded and exaggerated and designed to end on a punch line that went, “Those girls thought I was a total womanizer! I get that a lot, chicks accusing me of being a womanizer.”

“Awesome,” I said, hoping he was done, “Sounds like you have a lot of experience!”

“Bet your ass I do,” he crowed.

There was a smugness in his voice that made me think he was probably reclining with his feet up on a desk or coffee table. I took the long lingering moment as an opportunity to pounce and blurted, “Hey so how about we meet Friday night? At 11? I’d be happy to take the subway to wherever works best for you.”

“I’ll do you one better, rookie. Meet me in an hour on 68th Street and Lexington. And you’d better not make me wait.”

Rookie Sass

I double and tripled checked the street sign. There was 68th Street and there was Lexington Avenue, together on one pole. I was there 10 minutes early, and he was now 30 minutes late.

But that was just fine. I was meeting DatLadiezMan2, a real pickup artist. This was a man who chronicled his pickup escapades on the internet. And since no one’s ever told a lie on the internet, he must be legit.

I studied my reflection in a shop window. I felt like a schoolgirl before her first date. I licked my finger to sand down my sideburns. I spiked my hair up a bit. I adjusted my jacket collar. I spiked my hair down a bit. I was terrified DatLadiezMan2 would march up to me, look me once up and down, and deem me inadequate.

Behind me, a herd of people emerged from the mouth of the subway entrance. The commuters filtered left and right, scattering like a disturbed cloud of dust.

A text lit up my phone. DatLadiezMan2 wanted to know:

Where u @?

I looked up and scanned the urban landscape. No one fit the description of DatLadiezMan2. According to his message board profile, he was 28, extremely fit (“bordering on jacked”), great fashion, and classically handsome (“so handsome women often approach ME”). Worried I may have gotten the address wrong, I texted him my exact location, down to the storefront I was leaning against.

Within seconds, I had a response:

Tink I see u.

Again, I glanced around the intersection and saw what looked like a troll doll making its way across the street, heading toward me. A huge smile plastered across his ruddy face. Wispy orange hair seemed to be fighting a losing battle on his head, partly combed, but more wild and curly. His face was somewhere between old and young—but unmistakably ugly. He wasn’t laughably short, but the clothes he wore were way too big for him, hanging off his body like a boy who’d snuck into his father’s closet to play dress up.

This was not a man I’d ever accuse of being a womanizer.

As he crossed Lexington Avenue, he stopped in the cross walk to do a dance of sorts. After a little moonwalk, he pumped his arms to indicate, Raise the roof. He cupped one hand, brought it to his mouth, and howled at the night sky, “Cuckold on the prowl! Ca-cawk!”

A cab almost ran him over, causing him to scamper to the sidewalk.

“The Cuckold and his new sidekick,” he grinned, clapping me on the shoulder. “Women of New York, look out! You’re all in trouble tonight!”

No woman was in any sort of trouble.

I wanted to believe; for lack of a better metaphor, I wanted to believe like a kid tortured by the idea of Santa Clause. I wanted to believe the man in front of me was a womanizer, was classically handsome, was not a total creep from the internet.

I forced myself to smile. I squeaked out a strained, “Hi.”

I shook his hand when he said, “Call me Benjamin if that’s more comfortable for ya than Ladiez Man or Cuckold.”

He eyed me for a reaction. Seeing my blank stare, he added, “Just don’t call me a womanizer—least not in front of any ladies! Specially any married ladies!”

He exploded in laughter. I’ve never seen anyone find themselves so funny. The man was belly laughing for Christ sakes’—belly laughing! At his own joke!

I offered a sheepish smile. An awkward moment seemed to expand into eternity.

“Well,” I said, hope in my voice, “Let’s meet some ladies!” and clapped my hands together.

“Hey!” he shoved a finger in my face. “Watch your mouth. It’s called sarging. Learn your terminology, rookie!”

“Yeah,” I muttered, following him down a side street. “Sure.”

“Alright. Listen up,” he told me over his shoulder as we scurried toward 3rd Avenue. “Guys like me don’t need wingmen—we choose them. There’s a big difference. If you don’t know the difference, I won’t be choosing you again.”

I nodded.

“Another thing,” he continued, making a sharp left down 66th Street. “Guys like me have hobbies other than sarging hot babes. I’ve done things with cougars that would haunt your wildest wet dreams. Got me? Good. Maybe you’ll see me sarging tonight, maybe you’ll see me doing my own thing. You don’t have enough experience in the game to understand what I’m up to. Try to appreciate the magic, even if you can’t appreciate the magic. Got me?”

I nodded sheepishly, which caused him to stop, drape his arm across the entrance of a TGI Friday’s, and grill me, “I asked you a question! “You got me?“

I felt as if I were answering to a motivational speaker demanding a more energized response or a disgruntled bouncer itching to deny me entrance.

“Yeah,” I assued him. “Yessir. Whatever. Let’s just go meet wo–I mean, sarge.”

He inched the door open, glancing at me over his shoulder. “Already I’m not liking your attitude,” he told me. “You’re on notice, rookie.”

The TGI Friday’s was exactly how you’d expect a TGI Friday’s on a Tuesday night. I had no idea why DatLadiezMan2 insisted on “sarging” a chain restaurant when we were in New York City until it all became crystal clear when we walked up to the bar.

Immediately, DatLadiezMan2 made a beeline for a pinball machine off in a dark corner. He plucked a roll of quarters from his pocket and started to play. Once the silver ball was in motion, he looked as meditative as a Zen monk. His eyes glazed over and his fingers flailed, lighting up the pinball machine with a buffet of sound and light.

“What I love about this Friday’s,” he shouted over the drumbeat of pinball flippers, “Is this game. I’m always trying to beat my top score. I own every slot in the Top Ten. Wait till you see it,” he giggled. “You’re going to see, Ladies Man, Cuckold, Ben, Benjamin. It’s like a reunion for all my codenames!”

I watched in disbelief as this troll played on. Was this DatLadiezMan2—the Pickup Artist with the impressive cache of internet posts on picking up women? Really? I felt scammed. Little did I realize the scamming had only just begun.

I circled around the bar, scouring the place for approachable women. Even if I was in a TGI Friday’s, and even if it was a Tuesday, and even if I lacked the experience of a Pickup Artist, I was determined to make something of my night.

At the edge of the bar, I spotted two females—and that was enough. By dint of their womanhood, I was going to practice my “sarging” skills on them. As I closed in on the girls, I noticed one was actually halfway attractive…while the other looked about half the weight of a city bus.

I sidled up to the cute one, and asked for a female opinion on this or that. The cute one rolled her eyes, the fat one lit up. Fatty was elated to give a quick female opinion. I let her give it, and then made an underhanded comment about the cute one.

“What?” she screeched, “You can dress me up, but can’t take me anywhere? What THE FUCK is that supposed to mean?”

Panicking, I blurted out, “Woah! You know what I’d like to do with you guys? Dress you up as an angel and a devil—”

With that, the cute one really exploded.”You’re a fucking pervert!” She screamed into my face, “You won’t be dressing me up in anything!”

An embarrassed grin crept over my face. As I thought of my next line, a guy with a backwards hat marched over, arms crossed.

“What the fuck is going on?” He demanded to know. Then, pointing to me, he asked, “Who’s he?”

“He’s fucking rude is what he is,” answered the cute girl, “And disgusting!”

“Hey bro,” I said to the guy, throwing my arms up, “I will give you one hundred dollars to take this girl away.”

“No problem,” He sneered at me. “She’s my girlfriend you fuck.”

At that, he extended his arm. The cute girl hopped off her barstool and linked her arm into his.

“Come on Shelly,” he said to the fat one, “They seated us. Grab your drink, let’s go.”

The fat girl just stirred her chocolate martini. “I’ll meet you guys.” She said finally, looking down. “I’m gonna talk to this guy for a second.”

“Suit yourself,” Hissed the cute girl, prancing off with her boyfriend in tow.

I climbed onto a barstool, happy for an opportunity to get some experience under my belt. The fat girl looked down and shot me a sideways glance that would have been irresistibly cute had she been 100 pounds lighter.

Regardless, the girl was a total sweetheart. We chatted away. She overlooked my horrific game and I overlooked her rolls of fat. It was a match made in lowered expectations. Eventually the topic of jobs came up.

“I actually work for MySpace,” she smiled proudly.

“No way!” I exclaimed, “Do you know Tom? Tom is NOT my friend! But he’s my MySpace friend, what’s up with that?”

She giggled at my nerd humor. “Oh Tom,” She shook her head,”Did you know he’s gay in real life?”

“Holy shit,” I laughed, “I’m getting insider MySpace information! Wait a minute…”

I eyed her with suspicion, “How do I know you’re not lying? How do I know you don’t really work for Facebook, and you’re secretly trying spread rumors about Tom?”

“Here I’ll show you!” She shrieked, fishing into her colossal handbag, “Look, here’s my card.”

She held out her card to me. In that nondescript second, as I reached for the card, as “Sweet Home Alabama” blasted on jukebox, as the bartender was topping off a pint of foamy beer, as the fat girl’s face beamed with the possibility that a nice guy was about to take her card, DatLadiezMan2 made his move.

In what had to have been a full sprint, DatLadiezMan2 ran up from behind me and ripped the card from the girl’s hand. He’d plucked the card with such legerdemain that I didn’t even realize it was him until he was already circling the room. He ran up the back of the bar, brandishing the card over his head.

“Got it! Got it!” He boasted. “Number close!”

The fat girl looked at me horrified.

“What just happened?” She shrieked.

“I’m not totally sure,” I responded, watching DatLadiezMan2 do a celebratory moonwalk in front of the pinball machine. “Maybe my friend is drunk or something.”

“Hold on!” The fat girl stammered, looking at me with a face that was a mix of rage and sadness. “You know that guy? Did you guys plan this?”

“No! No!” I assured her, “Not at all!”

DatLadiezMan2 was still shimmying triumphantly, unfazed by the drama I was left to deal with.

“You asshole!” She belted, “I’m gonna tell Dan! He’s gonna kick your ass!”

At that, she pushed herself away from the bar and sprinted—surprisingly fast considering her size—toward the dining area.

Shit.

Across the dining area I spotted the fat girl, in tears (of course), pantomiming the story with wild arm movements. Even from where I stood, I knew I was being demonized. Backward-hat Dan looked enraged, jumping to his feet with the dangerous bravado of an insecure boyfriend looking to win favor with his insecure girlfriend by defending the honor of their even more insecure fat friend.

This, obviously, was not going to end well for me. So I ran.

I bolted from that TGI Friday’s as if chased by a bad decision. In a lot of ways, a bad decision was what I was running from. I ran from the threat of Dan, but I also ran from the truth of DatLadiezMan2. Was this the life of the pickup artist? If so, my legs couldn’t carry me away fast enough.