The Benevolent Pickpocket

There she was. Olive skin, dark black hair, brown eyes. She stepped out of her building and onto the cracked New York sidewalk, her black boots glistening in the unexpected but welcomed afternoon sun. Today, she was wearing a bright red peacoat that added a pop of color to the otherwise cold and dreary December day. I’d seen her around plenty of times before, but there was no way she knew I existed.

At least, not if I’d been doing my job right.

Olivia Madeira: 5’06’’, 28 years old, and allegedly addicted to her phone. At least, that’s according to Macey, her girlfriend of eight months.

That’s why I’d been following Olivia for the past few days. Her girlfriend had … heard about my unique skillset and gotten in contact with me earlier that week. One thing led to another, and here I was, half hiding behind a barren tree and watching Olivia as she made her way to the lunch date I’d told Macey to schedule with her.

Once Olivia crossed the street, I sprang into action. I’d done this grift dozens of times before, but I always got just a little bit nervous before making contact with the mark. I pretended to focus on my feet as I walked down the sidewalk, my eyes hidden just well enough behind my hair to let me surreptitiously track Olivia.

There weren’t many people out today, so this was going to be a bit tricky. But I’d made riskier moves before. And besides, this was for a good cause. Ever since I’d gone straight, pickpocketing had seemed to become much easier. As if the universe approved of my decision. Or maybe because I usually had the help of my marks’ loved ones to make it smoother.

Olivia was now only twenty feet away. I could hear the heels of her boots clicking across the cement. Ten feet. I could see the soft pink polish on her fingernails. Five feet. I could smell her perfume. One foot.

At the last minute, I stumbled sideways, pretending I’d tripped on the uneven pavement. Not my smoothest move, but it would work. I bumped into Olivia and sputtered a string of apologies. She grabbed my shoulder and, although a little surprised, didn’t back away from me like most people did.

I could see why Macey liked her.

Cycling through my usual apologies, I righted myself and avoided eye contact. Best if the mark saw as little of my face as possible. She asked if I was alright, and I mumbled my response before turning around and continuing forward. Again, not my smoothest exit, but it got the job done.

I turned the corner and waited a few seconds before peaking back around.

Just as expected, Olivia had continued walking. I wasn’t surprised. The lunch I had Macey schedule was at a little café just a bit farther down the street. I’d learned (through a few embarrassing failed attempts) that it was best for the marks to have as little time as possible to realize what they were missing.

Reaching into my pocket, I pulled out Macey’s phone—a brand new iPhone with a sleek red case that matched the peacoat she’d chosen to wear today.

This part was always the hardest.

My old self would be long gone by now, having nicked the prize and ditched Macey or whatever other sucker who had decided to trust me. I could feel the urge to flee writhe deep inside me, but by now I’d learned how to keep it under control. Who would’ve thought that a life of petty crime would be so hard to leave behind?

Although this new business model wasn’t nearly as lucrative as my old pickpocketing schemes, it definitely came with its perks. I knew it wasn’t the smartest move to circle back to the mark, but I hadn’t been able to resist lately.

It was just too much fun to watch everything unfold.

Across the street from the café, I watched through its large front window as Macey greeted Olivia with a smiling peck on the lips. I’d told her to be at the café waiting for Olivia—it was imperative not to give her time alone or she would definitely reach for her phone and realize it was missing. No, for the plan to work best, there needed to be as much time between me running into the mark and them realizing their phone was gone.

Once they sat down at a table, I walked across the street and eased my way into the café. It was crowded, which is one of the reasons I’d chosen it. It made this part much easier.

I slinked through the tight mass of patrons and sat at a table within earshot of Macey and Olivia. Shooing away the waiter, I nodded to myself as I heard Macey run through the list of approved conversation topics—no talk of weather, plans, or friends. These were all things I’d learned usually prompted the marks to pull out their phones, which isn’t what we wanted.

Eventually, once the waiter had come by with menus and taken their orders, Olivia inevitably reached into her coat pocket for her phone. Through my hair, I watched as her eyes widened and her hands began to pat all over her body as if she were on fire. I noticed Macey go stiff, but luckily she played it cool.

“What’s up?” I heard Macey ask as she casually sipped her water.

“My phone,” Olivia said with that now all-too-familiar restrained panic that I’d come to guiltily enjoy. “I can’t find it.” She continued to rifle through her pockets, as if searching enough would make her phone suddenly appear.

“Did you bring it with you?” Macey asked. “Maybe you just left it in your apartment.”

“No, I definitely had it with me,” Macey said, the panic now becoming more obvious, “I checked my Instagram on the way down.” She’d now begun to rotate in her seat, glancing around at the floor in cased she’d dropped it. Macey even played along and peeked under the table, pretending to look too.

I had to give it to her—Macey’s acting had been a bit shaky there at the beginning, but she’d really leaned into the role of supportive but not-too-concerned girlfriend.

“Are you sure you brought it with you?”

“I … think so.”

Macey’s question had just enough doubt to make Olivia second guess herself. Nice work.

“I’m sure it’s just back at your place,” she repeated. “We’ll go check when we’re done. Okay?” Olivia looked around, craning her neck to get a better view of the café entrance. She was clearly beginning to spiral, which usually happened.

Just like I’d coached her, Macey reached across the table and grabbed Olivia’s hand, centering her back in the moment. Olivia relaxed back in her chair and stared at her girlfriend, attempting a smile.

“Let’s just have a nice lunch together, no phones, and go check back at your place after. Okay?”

Olivia hesitated for a moment, bit her lip, then nodded.

Macey smiled back, and they continued talking until the waiter returned with their food. I ordered something myself and watched as the two spent the entire lunch date fully in one another’s presence.

I stayed the whole time until the waiter brought them their check. That was my cue.

Leaving enough money on the table to cover my own bill and a generous tip, I slipped out of the seat and stealthily made my way toward Macey. Just like I’d told her, she had a large purse hanging on the back of her chair.

Making sure Olivia wouldn’t recognize me, I quickly walked past the two of them and brushed up against the purse, quietly dropping Olivia’s phone into Macey’s purse.

I walked to the café door and, with one last glance behind me, looked at the two of them enjoying their time together.

My part was done.

I stepped back into the cold afternoon sunlight and wrapped my coat tighter around me. All that was left was for Macey and Olivia to go back to her place and search for her phone. Macey would place it somewhere in the apartment and help Olivia look for it until she “found” it. It was simple enough and never seemed to cause any problems for my other clients.

Olivia would feel silly for a little bit, and Macey may even feel like she’d done something wrong, but I’d assured plenty of clients that there was nothing wrong with wanting a little facetime with your partner without them constantly pulling out their phones. My methods may be a bit unorthodox, but the couples always seemed happier having spent a nice meal together without getting into an argument about not using phones.

Glancing down at my own phone, I realized I only had a few more minutes to get to my next appointment. In a city like New York, somebody had to help people make time for each other.