by Tyler Oakley
“Ohhh! Nice wicker basket!”
I couldn’t tell if the compliment was real. Had the basket been approved based on White House knowledge of the first lady’s passion for wicker? Or was she mocking me and imagining the hilarity of my flying across the country with this ludicrous object as my carry-on? Either way, it was approved, and this segment was happening. She casually answered my quirky questions, indicating zero knowledge of the drama behind the basket at hand. With the interview compete and a minute left on the clock, the first lady and I hugged. Over her shoulder, I locked eyes with the White House Official and smiled. When life throws a wrench in your plans, catch it and build an IKEA bookshelf—or in this case, an incredible collaboration.
The first lady has many passions and concerns for the world. While this campaign was about higher education, she also uses her influence to raise awareness of childhood obesity, with healthy eating being a staple of her messaging. Although I look back at our brief encounter fondly, when I’m asked what Michelle Obama smells like, I can’t help but recall the haunting scent of hastily discarded, bruised apples. Most likely, these were the only healthy foods ever disrespected in her name, and she had absolutely no way of knowing. Until now.
how fitting
ONE OF THE WEIRD, HOLLYWOOD-TYPE THINGS I have somehow been allowed to do is to host and report from red-carpet events. Back when I was in Michigan, the closest I ever got to the glitz and glamour of LA was my Hollywood-themed prom. A step and repeat was at the entrance, and volunteer parents lined up outside the gym to act like paparazzi. Somehow, this was only slightly less fake than life in LA.
Now that I live in Hollywood, I sometimes get invited to play the showbiz game, including red carpets, TV appearances, and award shows. When you watch these things from home, they flow seamlessly. It’s as if self-congratulating ceremonies with celebrities patting each other on the back are second nature to the Hollywood elite. But don’t be fooled! A lot of work goes into these things. Typically, this is a full-scale production, with stylists and makeup teams and hair people all primping and grooming their subjects. The number of man-hours that go into forty seconds on a red carpet would blow any Midwesterner’s mind.
When I first started getting invites to events, I’d show up and feel so inappropriately dressed and out of place. It was like I wasn’t even the same species as these people. I’d be surrounded by celebrities, each being lint-rolled and straightened and adjusted and perfected by stylists, while I stood in an ill-fitting suit, plucking off my own lint like a shunned chimp. Celebrities stood tall, smoldering into the camera. My posture looked Neanderthal, and my expression looked as though a human child had just taught me what smiling is. I’d then move to my spot on the press line, where I’d attempt to string together sentences that made vague sense, as sweat dripped down my protruding brow. Celebrities looked at me like I was an intern or a contest winner at best—at worst, I was a crazy Twitter fan that had photoshopped and laminated a press pass.
Luckily, these A-listers had mercy on my poor soul, and they approached my interviews with patience. Over time, I’ve kind of grown out of my awkwardness, and now I’m able to act like a human on red carpets. In my time spent interviewing celebrities, I mainly struggle with the temptation to ask them to follow me on Twitter.
Over the years, I’ve collected a few highlights on red carpets, typically from the most unlikely interviews. Yeardley Smith, the voice of Lisa Simpson, used her interview with me to promote her line of purple suede pumps. I basked in her glory and let her self-promote shamelessly. Julie Bowen, best known as Claire Dunphy on the sitcom Modern Family, asked me during an interview how I was allowed to be up past my bedtime. It was 5:00 p.m. on a Sunday. I once told Paris Hilton that her song “Stars Are Blind” changed the music game and was an anthem for true music lovers. I’ve discussed butts with the boys of 5 Seconds of Summer, and I used my interview with Nicki Minaj to thank her for retweeting me, six years after the fact.
When I approach red carpets, I always think of what Oprah recalls as the single most important lesson she’s learned while doing television: we all want to be validated. Oprah said that after almost every single interview (of the thirty-five thousand she’s done in her career), the interviewee turns to Oprah and asks, “Was that okay?” Knowing this, I try to remember that everyone is just trying their best, me included. Sure, some people are better known than others, but that’s not a reason to be intimidated by them. If anything, I’ve found that the more famous someone is, the more they just want to be seen by one person, in one moment, and to have some spontaneous fun, for once, in their overly regimented day. As I’ve worked more and more carpets, I’ve tried to just enjoy it. You can study all you want, and you can prepare certain questions for certain attendees, but once the carpet starts, you have no clue what is going to happen—except that people will show up and want to be seen, heard, and understood. In the monotony of the same questions over and over, they’ll hope for a few fun ones. My goal is to see them, hear them, and to goof around for a few minutes.
After a few years of working the carpets for the MTV VMAs, Kids’ Choice Awards, the MTV Movie Awards, and various TrevorLIVEs, I started to see more and more opportunities come to me. In 2015, I got my first offer to work the red carpet of the Grammys, and I was thrilled. For previous red-carpet gigs, I had always simply gotten dressed the morning of wondering, Okay, what’s going to make me look minimally lumpy today? As someone who has been on the Worst Dressed List and described as “Caesar Flickerman’s bastard son,” I’ve developed a sense for what fashion critics are looking to eviscerate. For the Grammys, I needed to look good. I wanted something tasteful but fun, classic but edgy, colorful but understated—so I hired a stylist.
After a couple fittings in which I picked out some favorite suits, I decided to borrow an olive-green Armani suit with a navy shirt and pocket square and a silver-striped tie. The morning I arrived to work the Grammys, my stylist was there to help me put on the finishing touches, and I felt incredible. The suit was tailored for my exact measurements, and I felt that I finally belonged among the red-carpet tribe.
After a full day of promo shoots, interviews, and walking the carpet myself, the team cheered as we called it a wrap. Though I loved my suit, nothing beats a pair of sweatpants. I shed my Armani and opted for pajamas for the ride home. With a paper bag full of the day’s borrowed outfit between my legs in the backseat of the car, I sighed and smiled, savoring the success of the day. I closed my eyes and daydreamed. Maybe someday I’ll have a stylist for every event, or even better, one for my own talk show. I imagined custom-made suits to make me feel comfortable for every night in front of the camera. Someday. My driver slowed to a stop, and I opened my eyes. I grabbed my Armani-filled grocery bag, and I stepped out of the car and into my apartment. Completely exhausted, I dropped my things at the entrance and called it a night.
The next morning, I woke up to the sound of my 6:00 a.m. alarm, and I groaned while crawling out of bed. I had to be on the NBC lot for a 7:00 a.m. call for an Access Hollywood shoot, recapping the Grammys. Normally, it takes me thirty minutes to even get out of bed, but somehow I was up, showered, dressed in a fresh suit, and ready to go—all way ahead of schedule. I decided to use the extra time to clean my apartment. I did some dishes, put away some laundry, and emptied all my garbage cans. Deciding to take all three bags out in one trip, I struggled through the back door and threw them into my empty Dumpster. As I got into my car, I saw a homeless man rifling through my neighbor’s trash, with a grocery cart full of cans beside him. While many of my non-LA friends were typically mortified by this sight, I’ve gotten pretty used to it, unfortunately. LA has a huge homeless population, and you’ll often see many of them going through recycling bins for cans and bottles to return for cash.
I got into my car, made my way to the NBC lot, filmed my segment, and headed back home. During my drive, I got a call from my buddy Korey, who had just received word from my stylist that the Armani
suit had to be returned that day. Unsure if I’d be home when they planned to pick it up, I asked Korey to head over to my place.
After twenty minutes, I got a second call from Korey. “Where did you say the suit was?”
“In a paper bag somewhere? Maybe near the front door?” I was focused on the road.
“I looked everywhere. There aren’t any paper bags anywhere.”
My stomach dropped. In my hurry that morning, while cleaning my apartment . . . no. I couldn’t have. In complete disbelief, I involuntarily burst out laughing.
“What?”
“I think”—I began, in between gasps of laughter—“I think I threw it away?” I screamed hysterically while cackling, “Korey! I totally threw it away! Oh my God, I am five minutes away. I will meet you at my back door. Be ready to hoist me into the Dumpster.”
After I parked, I scurried to my back door, where I found Korey peeking into the Dumpster. I laughed maniacally as I approached, still shaking my head at how clueless I was.
He cringed as I got to him. “I don’t think it’s in there.”
I brushed by him and opened the top of the Dumpster to peer inside. Sure enough, it was completely empty, just like this morning, except for two of the three garbage bags I had thrown inside hours earlier. Missing was the third and final paper bag. I knew what had happened to it. Somewhere in West Hollywood, a homeless man was collecting cans and bottles from recycling bins, clad head to toe in custom-fitted Armani (just not custom-fitted for him). I called my stylist to let her know what had happened, positive that this was by far the worst first impression I could ever make with anyone.
Now, every time I throw garbage into that Dumpster, I can’t help but double-check to make sure it’s not a $3,000 suit. I like to imagine that someday, ten years from now, when I’m on my way to my job as a late-night-talk-show host, I’ll be stopped at a red light. I’ll look over to the people at the bus stop, and he’ll be there, a tall, lanky homeless man in an olive-green Armani suit, fully tailored to a size completely unlike his own.
Side note: A few months later, on my twenty-sixth-birthday weekend, I developed a stomach flu. It was terrible timing. I had to cancel going to an award show, postpone my birthday plans, and cancel a trip to Hawaii. As part of this glorious weekend on the toilet, I had to return a stool sample to my doctor, so he could make sure no small creature was living inside my stomach. In my dizzy, dehydrated frenzy to get out of the house after three days of terrible diarrhea to take my shit to the doctor, I also grabbed some of the garbage that had been piling up at my front door. I tossed it all in the Dumpster and took three steps before stopping in my tracks, realizing that I had tossed it all in—shit included. I needed that shit. That shit was important. My doctor specially requested it. After months of diligently making sure that nothing I threw into the Dumpster was anything more valuable than actual human feces, I had accidentally thrown my actual human feces into the Dumpster. I couldn’t go to the doctor without it, so I pitifully hoisted my frail body in to pull it out. On your twenty-sixth birthday, nothing says adulthood more than fishing your own shit out of a Dumpster.
ten cummandments
SAN FRANCISCO TAUGHT ME A LOT OF THINGS. For example, some people have the innate ability to wink at you, while walking in your direction, while peeing! Also, if you live in the Castro, you can sometimes go weeks without seeing straight people and forget they even exist! But my favorite lessons of all had to do with sex. In such a sinner’s town, it’s curious to think that with what I learned, I could write a Bible of teachings. So, without further ado, please enjoy . . .
The Ten Cummandments I Learned While Living in the Bay Area
THOU SHALT NOT FANG BANG
In a town where everyone lets their freak flag fly, I guess I shouldn’t be surprised when I meet people who are unashamed to announce their fetishes early on in a relationship. This is, of course, a town that hosts festivals like the Folsom Street Fair—an outdoors celebration of all things BDSM, where leather is mandatory, and I once saw a woman willingly getting her “downstairs” whipped. These things happen in broad daylight in the streets of San Francisco, so what did I expect of the gentlemen I met in the shadows of the city’s gay bars?
One of these fellows showed no out-of-the-box quirks at the bar, and he was kind enough to let me crash at his place. This is where I quickly learned the level of drunk I needed to be to ignore weird things during sex—meaning, I was way too sober to be hooking up with a guy wearing fangs. No, they weren’t the plastic, glow-in-the-dark ones you get out of a gumball machine—these were the real deal. Okay, not real as in attached to an undead Transylvanian aristocrat—they were just expensive-looking veneers. This was not my cup of tea, but at least this man respected his kink enough to go first-class all the way. Listen, when it’s 2:30 a.m., desperate times call for desperate measures, so you’ve gotta let Count Fuckula drain you dry. (No twinks were harmed during the learning of this cummandment.)
THOU SHALT TAME THY MANE
Some people are hairy. I can appreciate this, but everyone has his limits. During my San Francisco days, a guy spent the night. The morning after, he sat up against my headboard, arms spread, inviting me to come cuddle into him. Half-asleep and without my glasses, I moved into his embrace, until I felt like I was being smothered by some type of musky wig.
Bewildered and mortified, I rolled away on the bed to grab my glasses, and I looked back to find him smiling, sitting upright, hands behind his head. His overgrown armpit bushes were a visual assault, like a glob of spit or a booger, I couldn’t look away. I didn’t know what to say or do. So I just sat and fumbled on my phone and waited to see how long he’d sit like that. Eventually, he took one hand and slowly lifted it toward the opposite armpit, where—no exaggeration—he began to run his fingers through it. Every man has his limit, and apparently mine was his finger-combing his Rapunzelesque armpit locks.
THOU SHALT NOT STEAL
After one particular adult slumber party, I awoke to find my new friend hopping into his jeans, trying to make as little sound as possible.
“Leaving so soon?”
“Yeah, I’ve got a brunch to get to. . . . Don’t worry about me, go back to bed,” he whispered as he leaned over to kiss me. I stretched and snuggled into my pillow, closing my eyes and whispering good-bye to him.
About an hour later, I woke up again to the sound of my roommate, Korey, yelling from downstairs, “Did you use my hair stuff?” I heard his footsteps coming up my stairs, and he tapped on my door. “Where’s my hair stuff?” He peeked through the crack of my door.
“I don’t know . . . just use mine.”
He returned downstairs and a moment later yelled up again. “Yours is gone too!”
My eyes shot open, in shock and disbelief. I leaped out of bed and flew downstairs to see what else might be missing. That motherfucker had come over, slept in my bed, cuddled with me all night, and left with my hair products. This is why we can’t have nice things.
Just as Korey had said, our bathroom cabinet was completely empty, with all styling pastes, waxes, and hair sprays missing. Yet, nothing else seemed to be gone. Even my laptop lay untouched, out in the open, right next to the front door. Our thief had no desire for expensive technology—no, this sicko craved something specific: a perfect and effortless quiff. I may not remember his face, but I will recognize his hair, and when I do . . . revenge will be mine.
THOU SHALT BE THIS TALL TO RIDE THIS RIDE
It’s no secret that I dig shorter guys. Or, if it was, now you know. This is not to say I won’t also date and/or love taller guys. Times are tough, and beggars can’t be choosers.
I met one short guy while I was getting pizza one night at 2:00 a.m. He was probably five feet two, with a compact build and a charming smile. After a bit of conversation, I found out he used to be in the army—I was into it.
He spent the night, and after he left in the morning, my roommate, Korey, appeared, determined to get the gossip
on the night before. While we chatted, Korey noticed a step stool in front of my window, awkwardly out of place. We both looked at it, then at each other, curiously.
“Why is that there?” he asked.
“I . . . have no idea.”
We sat for a second before it hit Korey: “He was too short to reach up and close the blinds!”
Korey burst out laughing. I screamed and clasped my hands over my mouth, trying not to wake the neighbors.
THOU SHALT NOT LEAVE YOUR FAVORITE SWEATPANTS BEHIND
No matter how much you like a guy, you never know when things may turn sour. With this in mind, it’s imperative to keep all of your beloved items in your own possession, even if things seem to be going well at the time. I once dated a boy in San Francisco, and I left my favorite pair of Okemos High School wrestling-team sweatpants at his apartment. After a long weekend out of town and a few curt texts back and forth, I quickly realized I was probably not going to be seeing him anymore. Worse, I wouldn’t be seeing my favorite piece of athletic apparel ever again. Don’t repeat my mistake.
THOU SHALT AVOID TRAINERS
I once developed a weird cuddle relationship with a guy I met through a dating app. He was conventionally handsome, a personal trainer with a body that was borderline upsetting, and the perfect big spoon. We made a habit of hanging out and watching a movie, after which he’d log on to his IMDb account and give it 8 stars. It didn’t matter if Meryl Streep gave her all-time best performance, or if it was Fifty Shades of Grey. We’d then fall asleep spooning. Nothing sexy, just some good old-fashioned half-asleep grinding. This happened a few times, right up until I finally encountered his true, weird colors.
