Flavor of the Week: Spy Girl Guilt

It was a holiday weekend and all my friends were out of town, which left me in the city with nothing to do. Inevitably, I turned to Craigslist to cure my boredom. I intended to find some cheap and easy writing gigs, but then I stumbled across something much more elusive in the creative section. “Wanted: Spy,” the title read. Obviously I clicked it.

“I’m looking for someone to spy on my girlfriend. I think she’s cheating on me. Will pay $75 for one night of work.”

At first, I thought I had stumbled across some Bored To Death super-fan trying to mimic Jason Schwartzman’s character’s dubious episodic motivations, but the more I dissected the post, the more convinced I became that this guy was for real.

I conjured up an image of myself sipping a martini in a bar watching someone’s unfaithful girlfriend tonguing someone two stools over. I’d slyly snap a photo with my phone and hit send, just like Gossip Girl trained me to do. It sounded a lot more fun than spending the night revamping someone’s resumé. I hit reply and volunteered for the job, trying to play it cool, saying I was bored and needed the money. I included my phone number in the signature. Within minutes, my phone rang.

“This is John. I posted the spy ad.

Are you free tonight?” he spit out, all in one breath. During our 10-minute conversation, John—most likely not his real name, I assumed—spilled his heart out to me. His girlfriend was pressuring him to marry her, but a mutual friend told him she was a cheating whore, going out on the weekends and hooking up with random guys. John lived across the country, so he couldn’t stalk her himself.

He said his girlfriend was Jewish and abided by the Shabbat rule every Friday, telling him she couldn’t use her cell phone to call him. John was suspicious this was just a ruse so she could go out and party without him knowing.

“This is what I want you to do,” he explained. “I want you to go to her apartment and see if she’s home, like she should be. You’ll be able to tell because she lives on the first floor and you can easily see into her living room. If she’s not home, then I’ll know she’s out partying and likely cheating.”

“You’ll pay me $75 just to walk by her apartment?” I asked, hoping my days of writing other peoples’ resumés were over.

“Yep.” Walking to the subway, I felt a rush of excitement. Who knew what I would find going on in that apartment! But as I walked down Second Avenue in the dark, thoughts of the Craigslist Killer crept into my mind. What if I was about to get murdered by some maniac? I pulled out my phone and sent a text to my friend Jordan: “Hey. I’m on my way to spy on someone’s GF. It’s a gig I found on Craigslist. Can you text me in a couple hours to make sure I’m alive?” Satisfied that I put safety first, I got on the subway and made my way uptown. Fifteen minutes later, I saw that I had three missed calls from John and two texts, one from John and one from my friend Jordan. Jordan: “You’re nuts.”

John: “What happened to you??????” I called John. “Hey, I was just on the subway…” “Are you there?” he interrupted. “Um, three blocks away.” “OK… Are you there now?” “Um… no.” A couple minutes later I arrived at the address he’d given me. The living room light was on, and I could see The Daily Show on TV. No cheating sex going on that I could see.

“Hey John, I’m there. I just walked by. Everything looks totally innocent. The Daily Show is on.”

“Oh, she loves that show. Do you see her?” “No. I’ll walk by again.” I walked by the window three more times, but couldn’t see anyone in the room. “I don’t see anyone in there.”

“Hmmm… This worries me.” “It seriously looks totally innocent,” I said to my employer.

“She could be having sex with someone in her bedroom right now,” John said. “Listen, can you go to the Starbucks around the corner for 15 minutes and then go back to the apartment and look again? I bet you’ll see two people in the living room. What a cheating slut.”

I was cold, wanted to go home and thought this guy was being paranoid. Ever the dedicated spy, however, I agreed. But instead of going to Starbucks, I went to Duane Reade to buy toilet paper.

As I compared Charmin with Scott, I thought about how John’s girlfriend had no idea her boyfriend hired someone on Craigslist to spy on her and that a “spy” had been peering into her living room window just minutes ago. I gave that relationship a 1-percent chance of working… But secret agents do not place judgment, so I bought my TP and went back to her apartment.

Again, I saw nothing. Only an empty living room with Jon Stewart on TV. I knew John would be disappointed. He wanted some sort of damning evidence. As his spy, I had a lot of power. I could really mess with his life. I could make up a lie saying I was witnessing some scandalous sex going on right that second. Or I could write a note to his girlfriend and slip it under the door, probably ruining their relationship. But I decided to be honest. I dialed John and told him nothing was going on. “Well, I still think she’s a cheating whore, but thanks,” he said. Then we hung up and I went home.

The next day, John texted me: “I feel bad about spying on my girlfriend, let’s not do that again.” The following day, he texted again: “Are you free to go to a restaurant tonight? My girlfriend is having dinner with someone, and I want to know who.”

I debated saying yes, but in the end I didn’t do it. I started to get my own suspicions about my distrustful employer. Perhaps this was his idea of kinky roleplay? Besides, I knew answering Craigslist ads like this could become a slippery slope. One day, I’m spying on someone’s girlfriend for $75. Then the next thing I know, someone would be sucking on my toes for 50 bucks. Thanks, but no thanks.