Chapter 4: The Pickup Artist’s Play

Just after my recovery, I went to see someone—Derek Shaw.

You wouldn’t find Derek in the Chamber of Commerce or Rotary Club. He’s the kind of guy who thrives in the shadows—always at the hottest new speakeasy, never on the VIP list but somehow behind the velvet rope anyway. The first time I met him, I was suspicious, but I’ve learned that the people you need most rarely show up in church clothes.

He’s a hustler I met at a bar, but also the most skilled pickup artist I’ve ever seen. I once watched him win over a stunning beauty with just a glass of water. Within a few days, he made a graceful exit, and the woman was left lovesick, swearing she’d never marry anyone else.

It was like watching a magician at work—sleight of hand, a knowing smile, just the right words at just the right moment. I took notes, not because I wanted to be like him, but because I never wanted my daughter to fall for someone like that.

Back then, I heard my second daughter was hanging out at bars with classmates. I was so worried that I invested in the bar they frequented, asking the staff to keep an eye on the kids and make sure nothing dangerous happened.

That’s what you do in my world—when you can’t control the chaos, you buy a piece of it. The manager gave me the inside scoop, let me watch the security footage when things got dicey. I never told my daughter. She’d have called it helicopter parenting and rolled her eyes.

Then Derek showed up, and the staff weren’t sure about him, so they asked me to come check him out myself.

It felt like one of those gritty detective shows on cable. I ducked behind the bar, pressed myself against crates of Bud Light, and watched Derek work his magic. Even the bartenders stopped wiping glasses to see how he’d pull it off.

I hid behind the bar and secretly watched his whole seduction routine. Afterward, I warned him not to hunt in my bar again.

My words were icy, but my hands shook. I didn’t want that kind of trouble for my daughter or her friends. Derek just grinned, as if he’d heard it all before.

He gave me a sly, seductive look with those fox-like eyes. Just that one glance, and I finally understood what it meant to be “captivating.”

There was something feral in the way he looked at people—like he saw straight through their armor. It made me uneasy, but also curious. He was dangerous, but not in a way that showed on the surface.

Luckily, I was already prepared for his type, or that look would have made my heart flutter too.

Experience is the best armor. I tightened my ponytail and reminded myself: I’m the boss here, not a guest.

Seeing I didn’t react, he lazily blew a smoke ring and said, “Too much of a mom vibe, not my thing.”

He didn’t say it to be mean—just honest, in that careless way some men have. A compliment and a dismissal all in one. I found it oddly reassuring.

Then he handed me a business card: “Let’s be friends. Who knows, maybe one day you’ll need me.”

The card was embossed with gold lettering—Derek Shaw, Lifestyle Consultant. I laughed out loud when I read it, but he just winked, unbothered by my skepticism.

At the time, I thought, why would I ever need a hustler? Didn’t expect to eat my words so soon.

Funny how life circles back around. The things you scoff at today might just be your lifeline tomorrow.

When I saw him again, he seemed even more dazzling than before, with a kind of wild, dangerous charm—like a vampire in the night, mysterious, dangerous, and oozing sex appeal.

He was perched on a barstool at some new downtown rooftop lounge, bathed in neon. People gravitated toward him without realizing why. His confidence was magnetic, but he always kept one eye on the exit, like a man with too many secrets.

The place smelled like spilled Coors and hot wings, neon beer signs flickering over the booths. Derek looked right at home. He grinned as I walked up.

“Well, look who finally tracked me down. Didn’t peg you for a dive bar type.”

He said it with a Southern twang, raising his glass in a mock salute. I rolled my eyes, but he got the message—I meant business.

“Mr. Shaw, you really are a prophet. I do need your help.”

He smirked, as if he’d always known this day would come. He gestured for me to take the empty seat beside him, the city skyline glowing behind us.

He raised an eyebrow, signaling for me to go on.

He didn’t say a word—just that arched brow, inviting me to spill my guts. I inhaled slowly, gathering my courage. Even now, asking for help didn’t come easy.

I described my predicament with the mistress, and my request was simple: seduce Lillian Moore, even just once. With Marcus’s personality, he’d never touch her again.

I laid it out, clear as day—no games, no subtext. I needed someone to knock Lillian off her pedestal, and Derek was the only one I could trust to get close without getting caught.

“A job this tough…” He stroked his chin, pretending to be troubled.

He drummed his fingers on the bar, eyes twinkling like he was auditioning for a role in a heist movie. I could tell he was sizing up the angle, not just the payoff.

“Name your price.”

My voice was steady, but inside, my stomach was doing somersaults. This wasn’t the kind of negotiation I ever pictured myself making.

“Someone like Lillian Moore has seen it all. Ordinary tricks won’t work. I’ll have to present myself as a diamond bachelor: luxury yacht, private jet, fancy cars, Rolex—the works. The activity budget can’t be small either.”

He listed it off like a shopping list, but there was a glint in his eye. He knew how to build a fantasy, and he wasn’t shy about the price tag.

“I’m not a sucker. You’ve already shown off all that on your Instagram. You own the clothes and accessories. For the rest, I trust a pro like you can find cost-effective solutions.”

I wasn’t about to bankroll his nightlife. I’d done my homework—seen his fake-it-till-you-make-it routine on social media. He flashed luxury but never paid full price for anything.

“Why are you so stingy? The mistress is at your doorstep, and you’re still not willing to bleed a little.”

He pouted, but there was no real heat behind it. Just the kind of playful banter that made him so dangerous in the first place.

“I don’t want to get conned before the divorce even happens.”

It was a joke, but only halfway. Every penny counted now. I needed this to work, not bankrupt me.

“You don’t trust me? Then why come to me at all?”

His tone grew sharp. Trust, it seemed, was the only currency that mattered to him. I folded my arms and waited. I’d learned not to blink first.

He pretended to leave, and I didn’t stop him. The bartender told me he’d been drinking cheaper liquor lately—probably not doing well.

I noticed the brand of whiskey in his glass—bottom shelf. The Derek I first met would never have touched it. Maybe desperation made us both bolder than usual.

“Hey, you’re really not going to beg me?” Sure enough, he couldn’t keep up the act and came back.

He leaned back in his chair, grinning sheepishly. In that moment, he looked less like a predator and more like a kid who got caught sneaking cookies from the jar.

“I’m the client, hiring someone to do a job. If you don’t want it, I’ll find someone else. There must be more than one outstanding graduate from your pickup artist training camp.”

My tone was icy, all business. If there’s one thing I’ve learned, it’s that desperation is expensive. I let him stew, knowing he’d take the bait.

He smiled, said nothing, but sat down again.

A silent agreement passed between us—two survivors in a world that didn’t care who went under.

“$10,000. If you succeed, I’ll pay you $10,000 as a service fee. The rest of the expenses will be reimbursed with receipts. You’ll wear a listening device so I can monitor the progress.”

My heart pounded as I slid the envelope across. This was my Hail Mary—and I hated how much I needed it. I slid a plain manila envelope across the table. Inside was an off-brand audio bug—cheap, but good enough for my purposes. He inspected it with a smirk.

“Deal.”

He extended his hand. I shook it, feeling a strange camaraderie. Sometimes, it takes a thief to catch a thief.

This time, he didn’t play hard to get and agreed right away.

He pocketed the bug and tapped it twice, like a magician priming a deck of cards. The deal was on, and the game was afoot.

Just as I was preparing to arrange a chance encounter for Derek and Lillian, he taught me what it means to be a true pickup artist. In less than five minutes, he’d already had his first intimate interaction with Lillian Moore.

I watched it unfold, slack-jawed, from the other side of the security cam feed. This was more than just skill—it was art. For a brief moment, I almost felt sorry for Lillian.