My High-School Boyfriend, the Con Artist

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Photo: H. Armstrong Roberts

This week, the Cut brings you True Romance: five days of stories about love as it’s actually lived.

My high-school boyfriend was a criminal. I met him at the ice-cream shop where we both, for a summer, worked. The ice cream was hard; I developed a tight right bicep. The shop was called Big Licks and the owner, before he was sued for copyright infringement, used the Rolling Stones’ logo on the company T-shirts. At 16 years old I basically daily left my house wearing a T-shirt with a gigantic mouth and tongue and the words BIG LICKS over my boobs. While wearing this T-shirt I asked stranger after stranger, Do you know what you want? and then I struggled to make the ice cream into a cone-able ball. My co-worker thought the noblest way to endure my daily pimp-out was to get drunk on the job. He’d show up to our shifts with a bottle of Kahlúa. He had dark eyes that tilted downward and made him look cartoonishly sad. He had a slight Irish accent. Pretty soon I was in love.

From the start our dates were more like stakeouts. My boyfriend, though gainfully employed at Big Licks, had material appetites beyond what his meager weekly paycheck afforded. What started as a petty-theft hobby turned into a side business selling secondhand fuzz-busters. Fuzz-busters were small machines that beeped if a cop was ahead with a radar gun; they helped speeders avoid tickets.

In order to make the fuzz-busters secondhand, however, my boyfriend had to steal them from the first hand. He knew the best places. We’d scope out parking lots of yacht clubs and country clubs, places where wealthy people who liked to break highway laws without financial recourse would trustingly leave their cars unlocked. We were white and my boyfriend drove a nice-enough car, so we were able to fib our way through the gates and wander the premises without being questioned or caught. He gleefully thieved in broad daylight. He sold the fuzz-busters to a man named Preston. Still, the fuzz-buster business wasn’t enough, or it wasn’t regular enough. He needed to augment. He had a tanning habit; he liked to get high and lie in a tanning bed and then drive around wearing the protective goggles. We also needed money to pay for a place that rented hot tubs by the hour. We went every day after school to have sex and this really added up. (We’d broken into buildings at the country club to have sex; we’d used the apartment of a friend’s recently dead grandmother and had sex in her hospital bed; neither of these solutions, while technically more affordable, were romantically tenable over the long term.)

He decided, in order to earn more money, to “work the system.” (This took work!) He, not exactly illegally, exploited the largesse of a local business that promised to take back any item of clothing or any pair of boots it had ever sold to anyone, ever, for a full cash refund. My boyfriend found boxes of his outgrown clothes from this store in his parents’ attic. At the returns center, a clerk would inspect the flannel shirt my boyfriend wore when he was 7 and say, “What’s the problem with the garment, sir?” and my boyfriend would say, “It doesn’t fit,” and the clerk would consult a bookshelf of old catalogues, and find the catalogue from 1975, and look up the shirt, and note the price, and hand him cash.

Other schemes were less exploitative, more proof (I told myself) of his nascent investment savvy and his tenacious work ethic. A very cheap airline began flying in and out of our local jetport; for $29 dollars you could book a seat, one-way, to New York. My boyfriend figured out which weekends the sleep-away camp sessions began and ended (i.e., the days when the flights to New York were sure to be overbooked), he’d reserve the maximum number of seats (I believe it was four) on each flight, and on those days we’d go to the airport and sit in the lounge and drink Bloody Marys and wait for the announcements prior to each flight: Anyone willing to give up their seat for $100, please see the agent at the desk.

Right before we broke up, we went to Mexico together — he’d made so much money from the airplanes we were able to go on a trip — but he invited a pot dealer named Spider we met on the beach to stay in our room with us, and they got drunk and started fighting, and I couldn’t handle the moral uncertainty anymore. When I got home, I told him: I was done. Though I hadn’t masterminded or even (really) participated in any of his criminal gambits, I was always along for the ride, and I certainly enjoyed being with him while he spent his money, and I know now, after watching various wives go to jail or at least endure the public shaming that accompanies one’s busted, sleazy spouse, that despite excellent grades and noble captaining of various varsity sports teams (these activities, I thought, were proof that I was just a tourist to the underbelly, that I was meanwhile safely on another path), I was not innocent.

Over the next five years, my (now ex-) boyfriend and I stayed in touch. While I entered the system, he continued to work it. Though he barely graduated from high school, he somehow, through back channels, convinced an exclusive university to admit him; he somehow convinced a tony social club to accept him.

After college, he moved to L.A. A friend, in a drunken rage, smashed my ex-boyfriend’s windshield. My ex-boyfriend had yet to find a job; the move had impoverished him. Driving around the freeways one day, he got an idea. He took down the phone number on the back of a dump truck. He called the number and complained that a rock had fallen off the back of the truck and broken his windshield. The company asked for a photo of the damage; an insurance company immediately cut him a check for $500. My ex-boyfriend postponed his job search. Instead he drove around and wrote down the numbers on the backs of trucks and filed complaints and collected money under an alias. He’d made about $12,000 when he called the same insurance company twice. They sent an agent to his apartment to investigate (he hid in the bathroom until the agent left). He packed his bags and fled town before the police showed up.

Unfortunately, his problems followed him. He had thousands of dollars of credit-card debt on many different cards. He was in some kind of additional trouble, but here is where my facts get soupy — we were no longer in touch. Somehow his debt was erased (or dodged), and possibly with the help of his sweet Irish parents, who’d always been entirely mystified by their son (he also stole money from them), he changed his name so he could start life anew. I heard through friends that he not only had a new name, he also had a new girlfriend — the first serious one since me. I was jealous. She was from Sweden; she wanted to be an actress. His girlfriend didn’t speak any English, but nonetheless, I was told, they really were in love.

A few months later I met her. I was walking down Columbus Avenue in New York, where I’d recently moved. I spotted my ex-boyfriend in the window of an Italian restaurant with his new girlfriend. She was blonde and tall; she shook my hand and smiled a lot. My ex-boyfriend, meanwhile, seemed uneasy with his new identity. I sensed in him a slight melancholy or the lowness that comes from lack of focus. Life was maybe not as interesting to him when he wasn’t constantly eyeballing unique ways to exploit it. He really was a con artist. It’s also hard to claim the following, given all the trouble he caused, but he was also a really good guy. He was a good boyfriend. For example, he called me right after 9/11 to find out how I was. To cheer me up, he told me a funny story. Remember that Swedish girlfriend? he asked. The one I’d met in the Italian restaurant? Well, he said, she turned out not to be Swedish at all. She was an American girl from Wisconsin who spoke perfect English. We laughed at how just it was that he should be the victim of a con. They stayed together for another six months; eventually the relationship died a more natural death. That he didn’t break up with her for conning him was proof, to me, of his incredibly just heart. He said that the brilliance of her deception made him love her even more.