College was going to be fucking awesome! It was 1993, and I spent a good chunk of that last year of high school sending off letters to UCLA, USC, University of Miami, Boston College, and anywhere else that had a media program, requesting admission forms. This would be my total reinvention. I didn’t have big dreams of good grades and graduating with honours, but I knew damn well I could be a legendary student. I wanted to be Rob Lowe in St. Elmo’s Fire, tortured and lost, sitting on the roof of a frat house with a saxophone, a cigarette, and knock-off Ray-Bans. Partying half-naked with girls who were also half-naked, while chugging beer and dancing around to Def Leppard. I wanted football games and pep rallies. Drunk, popular, and falling in love. Having my goddamn heart broken. I could be that guy. I was that guy.
None of that happened.
My high school grades left me with very few college options. Actually, they left me with just one option: the radio broadcasting program at Humber College, about a forty-minute drive from the town I grew up in. I applied to exactly one school. I never wanted to be a DJ. I only ever wanted to be an entertainer—I wanted an audience. Humber had a decent, well-respected radio program, and more importantly they had dorms, which meant I wouldn’t have to live at home with my mom and dad and commute in every day. A school with a dorm was my top priority, and these were single rooms—no roommate. They had cable TV, you got your own phone, and you could smoke.
I certainly didn’t get accepted because of my grades, or my in-person audition, which involved me reading an old traffic report along with a made-up commercial script for chicken tenders in front of the entire admissions team. My voice was a little deeper at this point, but even still, two weeks before my audition I remember chain-smoking cigarette after cigarette and screaming into my pillow at night trying to destroy my vocal cords just enough to give me a great voice. None of that helped.
I got accepted because I was the only person in that room who had real-life experience inside an actual radio station.
Every Saturday night during my last year of high school I’d sit on a bus for two hours to go and work in Toronto, for free, at a rock radio station—the biggest one in the country. I’d run the mixing board for the DJ, load up the CDs, organize the commercial carts, and press Play on the reel-to-reel machine if we were running something on tape. The studios were incredible—state of the art—and there was a punching bag and a grand piano in the lobby. The piano was just for show, but the punching bag was set up because the general manager got tired of the hotheaded sports reporter punching holes in the walls every time he got into an argument with the boss, or at least that’s the story they told. The halls were lined with autographed gold and platinum records from every band I loved.
There was a kick-ass Jock Lounge with a purple felt pool table and a wraparound balcony on the twenty-fifth floor. Before that, I’d never met an actual DJ, and these dudes were gnarly. Old-school “jocks” with big voices, big egos, making big money. But here’s the crazy part: they all really seemed to hate what they did. Don’t get me wrong—they loved their own voices, and getting paid to sit around listening to Led Zeppelin was cool too, but my god did they hate the audience. If you called into a radio station, to them, you were a loser. A fucking idiot. They’d call you a “prize pig” or a “loogan,” whatever that meant. If you were a kid who called in to request a song? Forget about it—those assholes would keep you on hold for twenty minutes and then just dump all the lines, all at once, hanging up on you and everyone else. To them, this was hilarious. To me, it was heartbreaking, because I used to be one of those kids.
The day my dad helped me move into my college dorm was very much like the movies. That weekend, I remember, my mom stepped back a bit and let Pops have these moments with me. Nobody on my dad’s side of the family had ever gone to college before. My brother started the year before I did, but he was still living at home, so I was the first Weston to ever go off to college. My parents sold our house and moved into a rental to make sure we could afford it.
After Pops set up my room and hooked up my TV, I laid out the sheet set my mom got me for the single bed that I was way too tall for. My dad grabbed me and pulled me in. He didn’t say much, but he gave me one of those hugs of his—the best kind. “This is an incredible opportunity,” he whispered to me. “I’m proud of you. You got this.”
“Yeah, Pop. I got this.”
He was right. This was an incredible opportunity. So I did my absolute best to fuck it all up.
I didn’t know much about college. Hell, I didn’t know much about anything, but I certainly didn’t know that you had to take English courses in order to pass. Like actual English classes with book reports where spelling counts. I honestly thought I’d walk into radio school and spend all my time learning how to make pro-level prank phone calls while coming up with a killer radio name like Tarzan Dan or Brother Jake. For two weeks I tried to make Roz Bozwood happen, or Roz Boz for short. That did not happen. Because it was stupid.
I wanted classes on humour, improv, storytelling, and contract negotiations. I wanted to spend my days writing jokes and my evenings screaming into my pillow trying to perfectly destroy my voice. This was not that. There was no course called How to Be Howard Stern 101.
On the first day of class, our English teacher assigned a huge project right out of the gate. This was less of a test and more of a challenge. She knew nobody wanted to take the class, so she made it simple: “Anybody who gets above ninety-five on this essay doesn’t have to take this course and you’ll never have to see me again.” That was it. It was that easy.
I worked my ass off on that essay. For five days I spent every minute in the library, skipped meals, and watched zero TV. I crushed it. It was a literal masterpiece. I had never felt so confident about anything in my entire life.
The following Wednesday, I walked back into that English class and yelled “You ready for this?” as I one-arm-slammed that thing down on the teacher’s desk. “I look forward to never seeing you again,” I said with full snark and a half wink.
“Same,” she replied.
I got 21 percent.
I’d never seen anything like that before. My essay was so marked up, crossed out, and pulled apart it looked like redacted FBI testimony.
That was, however, the last time I ever saw that teacher again. I never went back. Everyone just assumed I aced it and I never said otherwise.
I was a kid who had incredible confidence but pretty low self-esteem. I’ve always believed that when you’re young, those two things are built in two very different ways. Confidence comes from people telling you you’re great. Self-esteem is built by doing things that are great. Accomplishments. I’d never done any great things. I had all the confidence in the world but would always lower the expectations I had for myself just to avoid failure. Nobody ever saw me fail. At anything. I couldn’t handle that.
Those first few months of college were different, though. I was now nineteen and could already feel the shine rubbing off me. My confidence took hit after hit, and my self-esteem was non-existent. I was irrelevant and invisible. It’s not that people started to expect less of me, it’s just that nobody cared. I wasn’t ready for any of this, emotionally or otherwise. I felt lost, I missed my brother, and even doing my best in the classes that I did like I was never going be good enough.
For the first little while I really did try hard to take part, to make the best of it. I made a few good friends, talked a lot of shit, did the Thursday pub crawls, and discovered that Jack Daniel’s and I do not mix. The thought, though, of having to stand out or impress anyone was killing me. I didn’t have that thing, that spark, that other people in my class had. I still had nothing to say.
It was cheaper for us to eat lunch at the strip club up the street than it was to eat in the dorm cafeteria. Giant bowl of spaghetti, garlic bread, and a large Coke for six bucks. You just couldn’t beat those prices, so that’s what we did. A couple of days a week, a few of us would hop the bus for two stops to hit up the Manhattan Strip.
This was always mid-afternoon, so transitioning from the blazing fall sun to a super-dark, neon- and smoke-filled club always felt weird. Oddly, a suburban strip club in an industrial area at two in the afternoon is not the happiest place on earth. The girls were all day-shift dancers who never expected much from anyone—certainly not from a gang of poor college kids who were only there for the garlic bread—but we were always respectful. We’d clap after each one of their understandably uninspired routines, and we’d all tip the bartender a buck each on our way out even though none of us were drinking. Every other customer was there alone. Solo tables. They’d smoke a few cigarettes and nurse the same beer for an hour while making small talk with the dancers. Nobody who walks into a strip club alone in the middle of a Monday does so because they’re looking for a good time. It’s where people go to hide. Where lonely people go to feel a little less lonely. Even if they have to pay for it.
On Thursdays, a stack of NOW magazines would be dropped off at the lobby of our dorm. NOW was very much like The Village Voice in New York, a free weekly paper with snarky editorials, ultra-liberal politics, in-depth artist interviews, and all the movie and concert listings for the entire week. NOW was our bible. We lived and planned our lives by that thing. The last few pages were all the same classifieds that most indie papers use to fund their operations. Buy & Sell, Missed Connections, local business ads, and hundreds and hundreds of listings for escorts, strip clubs, and chat lines. I’d never used a chat line before, but the ads were very provocative and over the top, and they had names like Quest and the Night Exchange. Sexy anonymous fun for sexy anonymous strangers.
The chat lines were always free for women, but men had to buy a thirty-dollar monthly membership. To get guys hooked, they did have a few free spots assigned to a separate phone number, and if you called and called and got lucky, you got in and were given five free minutes to chat. I didn’t have a credit card, so I’d spend hours getting a busy signal before getting through. Those free five minutes would expire, I’d get kicked off, and I’d start all over again. And again.
Once you got through, you’d have to record your name and a quick personal greeting. That was all that the women online would hear. You’d hit 3 on your phone to skip through the messages, you could press 2 to send a voice message, and pressing 1 would request a “live one-on-one private conversation.” Building enough of a connection and rapport, while getting kicked off every five minutes, made private conversations almost impossible. I’d get close, exchange a few flirty messages, say something personal but not in any way true, and hope for the best. I’d only hear their names; the rest was up to me. The ultimate goal was to eventually talk live, exchange numbers, and call each other off the chat line. For free. This would take hours of work, every single day. Absolute dedication.
I spent months waking up at six in the morning, trying the chat lines until my first radio lab class. Then I’d head out for spaghetti lunch at the strip club right after that, skip the rest of the day, and lie on my bed in my dorm room trying to connect with someone. Anyone. Most nights I’d fall asleep with the phone still jammed between my ear and the pillow, with my hand on the keypad after hitting redial a few hundred times.
I was rarely myself on those things. It was always easier to be someone else. A fake name, with a fake story and a fake life. I was used to that, and always assumed the women were all doing the same thing, so I never felt too bad about lying. On the chat lines, in that world, my name was Jack, and after much trial and error I’d come up with the perfect five-second greeting that almost guaranteed me private messages within seconds. I’ve never told anyone this before, and my god is it embarrassing. Mortifying. So let’s all agree that you’ll read this one time and one time only and never repeat it ever again—because it’s absolute cringe—but here it goes:
“Hey, this is Jack. Just looking for a nice warm voice to rub up against for a while.”
That was it. Fucking kill me.
Eventually, and inevitably, things escalated. I’d exchanged numbers with dozens of—maybe even fifty or sixty—women, and I’d spend almost every hour of the day missing class, locked in my room talking to strangers. We’d have these incredible conversations that became less and less about sex. Little bits of truth would break through the characters we’d created. I’d hear about their jobs, their horrible husbands, their broken marriages. We’d talk about our bodies, insecurities, and fantasies. We’d also laugh—we’d laugh a lot.
This whole thing became an escape and I became the thing they needed me to be. This was a connection, the thing I looked most forward to in most of my days. In some weird backwards way, it felt like an audience. I was performing. These anonymous women saw something in me that I didn’t know existed, and I could be whatever it was they needed. And none of the women could see me; they couldn’t see me tic or see anything else I wanted to hide. I’d just turned nineteen and these were the closest relationships I’d ever had.
Once I started meeting women off the line, there was no going back. I’d sneak out of the dorm, way past curfew, and take the bus into the city to meet up with someone my mother’s age at a bougie downtown hotel, or I’d head to a parking lot out near the airport and spend a few hours with someone else in the back of her minivan. I’d never felt more valued as a person than I did when I was there.
Before your head starts spinning, no, I wasn’t a teenage college gigolo, and no, I never took money—but everything was up for grabs. They saw something in me that was great, even if it wasn’t true. It didn’t have to be. I was whatever they needed, and I was goddamn good at it. For the most part, these were women who were alone or broken, who needed an escape from trying to hold it all together. And for me? It gave me purpose.
I bought a second-hand suit in a vintage store for when I needed to be a bit fancy, and I picked up a bag of my old glam rock clothes from my parents’ house for when I needed to be a bit more, well, that. Some dates lasted minutes, others the whole night. One woman found out I’d never been to the Olive Garden and took me there for dinner every night for an entire week. Another, who I was meeting for coffee at noon, showed up drunk off her ass in an American-flag bikini, took one look at me, and started throwing glass saltshakers at my head that she’d grabbed off the hostess stand on her way in. I don’t know what I did, but I sure as hell did something. But most nights, these meetings were exactly what you think they were—sexy anonymous fun for sexy anonymous strangers.
If that year taught me anything it was that having a one-night stand can be awesome but being a one-night stand feels pretty fucking awful.
I was building a life around short-term, frivolous pleasure, torching the idea of any kind of long-term growth. And yet most nights I’d come home feeling great about myself. Whether I was a shoulder to cry on or a body to climb on, if I felt like I helped or made any kind of difference, I was good. The other nights, though, the ones where I let them down, when I wasn’t the exact thing they were expecting, or when I’d get dropped off in the middle of nowhere with no way home, on those nights I’d head back to my dorm, flop on my tiny bed, and hit redial.
In 2014, Humber College inducted me into their Radio Alumni Hall of Fame.