“I need to think about it,” I said. “I should get going.” I took those shopping bags and I went straight to my car, looking down at the ground the whole way, intentionally avoiding eye contact with all of my classmates.
My sister was home when I pulled into the driveway, so I had to sneak into my own house like a cat burglar. I got into my room and quickly started getting changed. I used a dozen makeup wipes to clean my face before I was brave enough to zip over to the bathroom to take a shower. Then, I put on a t-shirt and a pair of jeans: what I normally wore on a normal day. I looked at myself in the mirror and I felt nothing.
But I could still see that beautiful face that looked so amazing in makeup. I could see those hips that were begging to be in a tight dress. I looked down at my legs and thought about how much of a shame it would be to let my leg hair grow back out. Then I found myself staring at my toes, wondering if they would be cuter with white nail polish or red—and that’s when I noticed the slip of paper on the ground next to my door.
I walked over and saw that it was a note written in my sister’s handwriting. “If you’re going to steal clothes from my closet, at least ask me first. I was going to wear that gold jumpsuit for my date tonight.”
My heart stammered and then the strangest thing happened: a smile crossed my face. I didn’t feel terrified or humiliated. Instead, I felt excited. The note almost read like an invitation to share my sister’s clothes.
I rushed over to my phone and typed out a message for Chris. “I want to be Riley,” I wrote. And I sent the message quickly. From that moment, I never looked back.
THE END
THE GAMBLE
Orrin’s comedy career was just taking off when he made that infamous tweet, claiming that he could always tell the difference between a real woman and a transgender woman. Now, he’s a pariah. No clubs will let him do his act, even though he deleted the tweet and made a lousy apology on live television.
But now he’s being given an opportunity to redeem himself, on a show called The Gamble. Each episode, the contestant makes a unique gamble. And Orrin’s gamble is simple enough: pick out the only two biological women from the line-up of six. If he chooses the two girls successfully, he gets fifty grand. If he accidentally picks a transgender, then he will face the biggest humiliation of his life, on live television.
CHAPTER I
I didn’t expect the backlash that I got when I made that little tweet. I thought people would just take it as a joke—all of the other tweets on my Twitter page were jokes, so I didn’t get why everyone was suddenly taking me seriously. And not to mention—I thought that everyone would agree with me. Even after the backlash, I still thought that most people agreed with me secretly.
It wasn’t like I was trying to offend anyone. I wasn’t trying to take away anyone’s rights and I wasn’t trying to get mobs together to hunt people down. I wasn’t a villain—just a comedian who made a dumb joke. I deleted the tweet after just twelve hours, but it was too late: the tabloids were already running with it and I was suddenly more famous than ever before in my life. And I hated to think that I was finally blowing up because of a bad joke, and not one of my many good jokes.
I had good jokes, too, believe it or not—but over the next few weeks, I wouldn’t get a chance to actually do my act. I managed to get booked at a club after a lot of begging with the manager, but I didn’t get a single joke in before I was booed off the stage. My friends were all telling me to make a public apology and then hide out for a year or two, or until the next comedian made the same mistake. But I couldn’t just stop working—I was a working comedian, and that’s how I made my living. Luckily, I was starting to make more money than ever off of my YouTube channel—though the comments people were leaving weren’t doing much to help my situation. Apparently, I’d found a new audience of far-right conservatives who liked to discuss topics like abortion in my video comment sections. Under one video, the conversation devolved into reasons Hitler should have won World War 2. Now I felt like I had an obligation to turn off commenting on all of my videos, but I was worried that if I turned the comments off, I would scare away the last bit of my revenue.
The tweet really wasn’t that bad. How bad can a tweet even be? You only get so many characters to work with, and I didn’t even come close to reaching the max. “We should call transgender girls something other than ‘girls’. I think we can all agree that they never really look like girls.” Sure, I was a bit drunk when I wrote the tweet—and it wasn’t that funny—but it really was just supposed to be a joke… Though I really thought it was true. I mean—I’d never seen a trans girl who was even a little bit convincing. Whenever I saw them, walking around the streets of New York City (and there were lots of them in New York City), they always stuck out like big yellow zits on a pale face. And don’t take that the wrong way—I’m not calling trans girls ‘zits’—I don’t need to go through that nonsense all over again.
But they were always obvious. It was never the short, skinny guys who tried to become chicks. It was always the basketball-sized guys with the broadest shoulders and the roughest jaws. They always had small eyes and what looked like clown makeup smeared all over their faces. And when they spoke, the ground practically shook, in case it wasn’t obvious enough.
The far-right crazies who tweeted me after I wrote the tweet all agreed with me, and I was almost starting to wonder if they were the right ones. At least they could look at the situation with objective goggles… Though I wasn’t fond of all the swastikas in my private inbox.
E! News reached out to me, asking for an interview. My agent urged me to take the interview and use the opportunity to make a public apology. He even urged me to take an acting class before the interview, so that I could learn how to cry in front of the cameras. I thought it was a silly idea, and then my agent e-mailed me to let me know that I was booked for an acting class. “If you want to keep me as an agent, you’ll go to the class and then you’ll make the apology. My son is transgender,” my agent said. And all I could think was: did that mean his son was a guy who thought he was a chick, or a chick who thought she was a guy? I didn’t ask.
I went to the class. One of the girls recognized me. She refused to do a scene with me and then she told the rest of the class about my tweet. And all I could think was: I just got recognized outside of a comedy club for the first time in my life. I smiled and then the teacher looked outraged. Thankfully I wasn’t kicked out of the class, but I didn’t exactly get a lot of time on the stage.
My E! interview was early in the morning. I wasn’t used to getting up so early, because my shows were usually very late—sometimes as late as midnight, and then the other comedians at the clubs usually wanted to hang out afterwards. Even though I wasn’t working, I was still sticking to my usual schedule, just in case I got booked.
I only got three hours of sleep before my alarm went off that morning. My coffee maker decided it wouldn’t work, and then my debit card was unexpectedly declined when I went to buy a large coffee at the Starbucks underneath my building. As I was leaving, the barista said, “My brother is a transgender, by the way!” And in that moment, I realized my debit card was probably working just fine.
I was tired and irritable when I arrived for my interview. My agent didn’t show up like he said he would, but that didn’t matter—I didn’t need him with me to say the word ‘sorry’. They rushed me over to the makeup desk. The woman quickly powdered my face, nearly blinding me—I couldn’t help but wonder if she was pissed about my statement as well. Maybe her mother was a transgender or something.
Then the sound guy quickly slapped a microphone on my chest. The AD rushed into the room and started waving his hands. “What’s taking so long? Let’s go!” I got up and followed him onto the sound stage. The lights were bright and there was an empty chair sitting in front of a large black backdrop. “Sit,” the AD said, so I sat. Then he yelled, “Okay, let’s lock it up and roll!”
“Sound is speeding!”
>
“Camera’s speeding!”
A man was holding a slate in front of my face. “Orrin Pearson interview, take one!”
“Mark it!”
He snapped the slate, making me wince. Then he rushed away and a man in a suit walked up and took the seat in front of me. He quickly straightened his collar and then he looked into my eyes. I recognized him, though I didn’t know his name. I probably should have asked one of the crew members for his name—but it was too late now.
“Okay, whenever you’re ready, Wolf!”
“Orrin—how are you doing today?” Wolf asked with a big smile.
I looked around and saw the red glow above the camera. Then I noticed another camera next to it, and another next to that one: three cameras pointing at me—maybe more lurking back in the shadows. There were two black microphones dangling above my head, being held up by nearby boom operators. And behind them stood a crowd of cross-armed crewmembers, all looking at me as if they had transgender relatives as well. “Me?” I said, suddenly feeling flustered.
Wolf laughed. “Yes, you.”
“I’m okay.”
“You’ve recently received some backlash for a statement you made concerning the transgender community.”
“It wasn’t a statement,” I snapped quickly. “It was a tweet—just a joke. And I deleted it because it wasn’t a very good joke.”
“It wasn’t a very good joke?” Wolf asked. “So it was just kind of a good joke? Do you think that transgender people are a joke?”
“No—I didn’t say that. Don’t put words in my mouth.” I looked around again. My heart was pounding and I felt like I was under attack. How was I supposed to apologize? I was the one who deserved an apology. All I did was make a joke and now the world was coming down on me as if I was Hitler reincarnated. “It was just a joke,” I said again.
“Just a joke,” Wolf repeated. “Are you aware that over one hundred transgender people committed suicide in the past month.”
“Is that true?” I asked.
He was staring at me with lowered eyes.
“Um, well no—I guess I didn’t know that. But that’s not the point. I didn’t make fun of anyone and I didn’t make any statements. I just made a joke—and then I deleted it. Doesn’t it matter that I deleted it? Are we live?”
“Orrin, how would you describe your comedy style?” Wolf asked, as if he wasn’t listening to a word I was saying.
“My comedy style? I guess you could call it observational comedy. I like to tell stories—sometimes longer stories, mixed with a few shorter—”
“—Would you call your comedy offensive?”
“Offensive? To who? No—of course not.”
He picked up a card off of his lap. “Margot Anderson from Tennessee saw one of your shows recently, and she tweeted afterwards: ‘Orrin Pearson’s show was the most offensive thing I’ve ever seen. I’ve never felt so hurt and attacked before in my life.’ What do you have to say about that?”
“Margot who? I don’t know anyone named Margot. That must be a mistake. My shows are clean. I hardly even swear. In fact, I do the occasional family friendly show. I did a high school just a few weeks before all this happened.”
“You think that your hateful message is okay to spread to children?”
Now I was starting to feel angry. I was being set up. This was a ‘gotcha’ segment if there ever was one, and I wasn’t going to take it. “Look—I’m sorry if you were offended by my joke. If you want to let it ruin my comedy for you, that’s your deal. But if you want to call me offensive or mean, then that’s just slander and I know some pretty good lawyers—I’ll have you know.”
Wolf nodded his head slowly. “So you’re saying that you’re sorry?” he asked.
I bit down on my tongue. I wasn’t sorry. I had nothing to be sorry about. Wolf needed to relax and his fans needed to relax; the whole world needed to relax. I thought about my agent and my career. I knew that I just needed to bite my tongue and capitulate, but I couldn’t do it. I just couldn’t pretend like I cared about their soft feelings. Comedy has no future in a world where comedians have to apologize for every lousy joke they make. “No,” I said. “I don’t apologize. In fact, I think what I said is true. Find me one convincing tranny and maybe I’ll change my mind.”
I heard a gasp from the crew. Wolf’s eyes widened and I realized I’d just made a big mistake. My professional career was over. If I could have gone back in time to make an innocent little lie, I would have—but I was stuck with the words that came out of my mouth.
CHAPTER II
My agent dropped me as a client and he even blocked my number from his phone after making a big public statement about how his agency doesn’t agree with my statements towards the transgender community. People were appalled at my use of the word ‘tranny’, though no one ever told me that tranny was a bad word. I just thought it was slang. How can a person keep up with the constantly evolving verbiage without a goddamn degree in gender studies?
I stupidly convinced myself that I could make it without an agent for at least a couple of years, until everyone forgot about the whole debacle—and then I could find a new agent. But it wasn’t so easy. I called up venue after venue, asking if there were any openings. I called all of my comedians friends, to see if they needed an opener—but even my friends didn’t want anything to do with my professionally. “Hey man, I hope you’re doing well, but maybe just don’t tell anyone that I answered the phone for you, okay?” said Jerry Knoll, one of my closest friends.
My bank account was quickly dwindling. I found myself eating packaged noodles every night while trying to save money. I figured if I could just last a couple of weeks, things would start to turn around. But that tweet continued to haunt me. There wasn’t a day that went by that it wasn’t reposted on Twitter, either by angry social justice types or by my new fans, some of which were still donning their swastika profile pictures. The story just wouldn’t die, and it was starting to seem like my career was doomed to die with it.
It was two weeks later when I received an e-mail with the subject line: BOOKING INQUIRY. I became excited, but I wasn’t holding my breath. The e-mail was sent to an account that wasn’t listen publically—only on my professional networking site, available only to booking managers and agents—but that didn’t mean that my e-mail hadn’t been leaked to pranksters and social justice warriors.
I opened the e-mail and found myself unsurprised by the message. “Like many people, we were especially offended by your tweet and interview about transgender females.” I nearly stopped reading, but since I had nothing better to do, I kept going. “However, we are aware that many people share the same views as you. It’s our goal to change the public opinion on transgenders, as many of us at Warren Media are transgender ourselves.” I rolled my eyes. “We’d like to invite you onto our show, The Gamble. Perhaps you’ve seen it—it’s available on Prime if you have a membership. If you don’t have a membership, please feel free to look up clips on YouTube to get an idea of what we do. The show follows a reality format, so there would be a camera team following you around of a week. We would be willing to pay up to one thousand dollars per day of filming. If you’re interested, please let me know as soon as possible.”
I had to look the show up. I didn’t have Prime, but I did find a full episode on YouTube. In the episode, a TV actor had one week to prepare for a running race against a female Olympic athlete. I skimmed through the episode. Apparently, the actor had claimed on Twitter that he believed that most relatively fit men could beat even the best female athletes in the world. I watched the race at the end of the episode, and the guy actually came pretty close to beating the chick. She won—of course, because she’d been training her whole life and the guy only had a week. I don’t think it was the blowout victory the show was hoping for.
Because the guy lost, he had dress up like a girl and run a half marathon. The footage was actually very funny because he was exhausted before the race was even
half over. He ended up throwing up while wearing a little pink skirt and a sports bra with pads for tits.
The episode didn’t give me any clue as to what they had in store for me. Based on what I said: that transgenders don’t look like actual women—I figured they would try to prove me wrong somehow. Maybe they would even dress me up like a girl and put me on the streets for a week to see if guys would hit on me. Was that worth a thousand bucks per day? I needed the money, but I didn’t need more humiliation.
I gave the club circuit one last try. I called up the managers and received a dozen rejections, and then I found myself wondering if this reality show could help my case. Maybe being embarrassed on television was exactly what I needed. Maybe I just needed a good opportunity to show the world that I could still be funny. If they dressed me up like a chick, I’m sure I could come up with some hilarious jokes. The Monty Python guys were funniest when they were all dolled up—and they were my heroes.
And maybe—just maybe—I could use this second chance to slip in a little bit of an apology, so that I could continue being a comedian, so that I wouldn’t have to start finding a new job as a dishwasher or a garbage man.
I got a call only a few minutes after sending the e-mail to the producer of The Gamble. “Hello, Orrin? This is Michael Sanderson from The Gamble,” he said. “I’m glad to hear that you’re interested in doing our show. Are you free on Monday to start filming?”
“What are you guys going to make me do?” I asked.
And I could almost hear the smirk in his silent voice. “We don’t want to ruin the surprise,” he said.
“Well I don’t want to do anything embarrassing,” I said.
“We won’t do anything that will hurt you physically or traumatize you emotionally. That’s about all I can guarantee, Mr. Pearson. I guess you could say that coming on our show is a bit of a gamble in itself.” He snickered as if it was the funniest joke he’d ever told.
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