Are You There, Vodka, It's Me Chelsea

planning to be done if I truly was going to prison: My first priority was to start thinking about what kind of gang I would join.

I hoped my uncle wasn’t still mad at me for choosing to have sex with a family friend instead of him when my cousins and I were playing the “Who Would You Rather Have Sex With?” game. The premise of the game is you have to choose between two people who you would rather have sex with-sober-or your entire family is killed. Usually, the choice is between two real winners like David Hasselhoff and Gary Coleman. A couple of weeks prior, when my fourteen-year-old cousin Madison asked me if I would rather have sex with her dad (my uncle) or their family friend Rusty, I of course chose Rusty, because he was not a relative. My uncle didn’t take kindly to this when Madison told him. He took it as a personal insult that I would rather have sex with someone I barely knew. “We are related!” I told him.

“That’s really shitty, Chelsea,” he replied as he took another sip of his double vodka and grapefruit. “I’ve been like an uncle to you.”

“You are my uncle,” I reminded him.

“Not by blood,” he replied.

A couple hours later a female officer came in and handcuffed me. “The bus is here to take you to Sybil Brand.”

“I hope you realize that you’re making a big mistake,” I told her. “My father works for the Department of Sanitation.”

“Well, then, you should have no problem getting released.” She smiled. She walked me on the bus and sat me down next to a Hispanic woman with two gold front teeth who looked like she was in her nineties. Then the female officer shackled our ankles together.

“Are you being serious?” I asked her. “Do you really think ankle cuffs are necessary? I am not an outlaw.”

“Standard operating procedure,” she replied.

I looked around the bus at all the other prisoners. There were close to twenty women altogether. The only race not represented was Asian, and I breathed a sigh of relief. Mandarin and Cantonese are two dialects I knew wouldn’t be easy to pick up, not to mention the pressure that would come with joining an Asian gang. This was years before the release of Crouching Tiger, Hidden Dragon, and my martial arts weren’t anywhere near the level they are today.

I looked over at the woman shackled to my ankle and made the peace sign.

She didn’t respond, so I had no choice but to vocalize it. “Peace,” I said, leaning in to make sure she could hear me.

“Peace,” she responded without looking in my direction.

I turned around to look at the two black women sitting directly behind me. One looked like she’d only be a voice if she lost any more weight, and the other was about four hundred pounds and looked like she was very close to eating the woman sitting next to her.

I lifted my chin and jutted it in their direction. “Word.”

A cold stare met my eyes from Fat Albert’s sister, and the skinny woman kept staring out the window, shaking. “You wanna get bitch-slapped, Barbie?” was the next thing I heard from a black woman sitting behind Fat Albert’s sister.

I was tempted to let Foxy Brown know that it wasn’t really possible for anyone to bitch-slap me with handcuffs on, but decided to keep a low profile. I turned around and wondered when Malibu had become so heavily integrated.

The bus ride lasted for about forty-five minutes, and I kept to myself the rest of the trip. It became clear that this wasn’t my crowd and that once I got to prison I would have to find the girls with good teeth and run with them.

Once we got to Sybil Brand, all twenty of us were put into a holding cell with benches, while they would call us out one by one to be booked and fingerprinted again. They unshackled us, and the minute Goldfinger was separated from me, she walked over to a corner of the room, pulled her pants down, and peed on the floor.

It was quickly becoming apparent to me that this situation was much more serious than I had realized. This was turning into a full-blown episode of Survivor: Women of the Outback. Not only were some of these woman behaving like wild Indians, but looking around the room, I knew that if I had any hopes of blending in here, I would have no choice but to get a tattoo.

Soon after we arrived, an officer came in with a bunch of sandwiches covered in Saran Wrap. You would have thought these women were getting food airlifted in a war zone. One woman was knocked to the ground as others ran to the officer bearing sandwiches.

How anyone could have a sandwich at a time like this was beyond my imagination. I stayed seated on my bench and watched this pandemonium in disgust. I avoided further eye contact with any of the women until finally my name was called.

I was taken in to be booked and fingerprinted. Again, I tried explaining to the officer taking my picture that this was a huge mistake, and that they shouldn’t bother booking me, as I was going to be bailed out at any minute.

“That’s what they all say, sweetie,” she replied.

“I’m serious,” I said as I turned my head to the side for my profile shot. “My father is black.”

She told me it didn’t matter what race my father was, and that even if my bail had already been posted, I couldn’t be released until I was entered into the system.

Next up was a strip search, or what I now refer to as anal rape. They took us in groups of eight into another holding area, where we were instructed to undress and stand a few feet away from each other in the buff. This news, of course, threw me into a hissy fit, as I tried to piece together when I had last had a bikini wax. It had been at least a month, and I knew it was not going to be pretty. Even though I am not an extremely unkempt girl, I make it a personal rule to never allow others the displeasure of seeing my beaver in an unruly state.

Turns out that I had nothing to worry about. Once we were all undressed, I realized the true meaning of “unruly.” There were women in there who clearly had never heard of a razor, never mind a bikini wax. Hedge trimmers would have been a more appropriate tool for the situations going on in between some of these women’s legs. One woman looked like she had Buckwheat stuck in a leglock.

As each woman bent over and spread her ass cheeks, I wondered what the officers thought they would find. “I’m sorry,” I blurted out. “I can tell you right now that I do not have anything inside my brown eye. You do not have to check it.”

“Ma’am, please turn around and bend over,” the female officer said to me.

“I just don’t understand what you think you’re going to find in there,” I said, standing upright with both hands covering my asshole.

“You’d be surprised, ma’am-drugs, pills, money. Yesterday someone had a Game Boy up in there.”

“A Game Boy?” I asked, horrified. I turned around and tried to relax my butt cheeks. “Were the batteries in it?”

“Uh-huh,” she replied as she motioned for me to get into position.

“I guess that gives new meaning to the term ‘junk in your trunk.’” No one responded to my joke, which I thought was extremely clever. I turned around and bent over. It wasn’t as unpleasant as I had expected, but I would have been much less inclined to put up a fight if the officer were male.

Afterward we were each given a bright orange two-piece prison suit and open-toed slippers. Fortunately the slippers really showed off my pedicure, but the orange prison garb was a total nightmare for my skin tone. I had found out years earlier that I was a “summer” and the best colors for me were pastels. I looked at the clock and saw that it was 7:30 p.m. If I wasn’t here, I would be leaving happy hour this very minute, most likely with someone of South American descent.

Finally, they led the eight of us into a room the size of a football field filled with rows of bunk beds. There were hundreds of women everywhere, and none of them looked Jewish. I was assigned to a top bunk in the middle of the room. The bottom bunk, I had to assume, was occupied by the large muscular woman doing one-armed push-ups next to it. I was given a bag of toiletries, and when I looked inside and didn’t find a pair of eyeshades, I nearly hit the roof.

The situation was growing worse by the minute. I looked at G.I. Jane and asked her if there was a manager around.

“Huh?” she asked.

“Hi, sorry, I’m Chelsea,” I said, putting out my hand. When she didn’t meet my hand for a handshake, I asked her who was in charge around here.

“Depends. What are you looking for?”

“Well, I’m not supposed to be here, so I need to talk to whoever’s in charge.”

“Go to the window up front; the guards don’t know nothin’.”

“Thanks,” I said, and walked over to the glass partition at the front of the room, only to be stared at by every woman I passed.

“She looks yummy,” I heard someone say as I sped up and stared at the ground. I was in no mood to fight off a sexual abuser. Normally I would never be one to report a rape, unless, of course, it ended badly. But if my attacker was a woman, that opened up an entirely new playing field.

When I got to the booth, there were about fifteen women in line ahead of me waiting to speak with the two women behind the large glass partition. It struck me that this was exactly like the DMV, except we were all wearing the same jumpsuits. There was a large Mexican woman in front of me with a shaved head and tattoos covering both of her arms. She turned around to look at me and didn’t drop her stare for thirty seconds. I had already learned through trial and error that the conventional “hello” or “word up” didn’t work here, so to break the awkward silence I had to try something new. “I like your head.”

She said something in Spanish and spit on my feet. Then she looked at me again for an uncomfortably long time. I gave her a closed-mouth smile to let her know I was totally cool with her spitting on me, until she turned back around. She had two large knots above the roll of fat that connected her head to her shoulders, and her back was the size of a suitcase. This was the type of woman you’d want on your side if you were up against a crocodile.

I looked around at all the inmates milling about. Some were in groups talking, one woman was rapping loudly with headphones on, and there was some sort of frenzy ensuing in the far corner of the room about fifty yards away. Then I heard yelling. “Ham-and-cheese sandwiches!” Again, I saw all the women flocking to one area as sandwiches flew through the air, some landing on beds, some landing in people’s outstretched hands. Everyone in line in front of me scattered and ran toward the sandwiches. It was a complete madhouse and gave whole new meaning to the word “picnic.”

I, of course, seized this opportunity to get to the front of the line and get some answers. “Hello,” I said to the officer sitting behind the partition. “I’m supposed to get bailed out shortly, so how exactly does that work?”

The officer was a pretty black woman who didn’t appear nearly as annoyed with me as everyone else seemed to be. “Well, someone needs to post your bail, and then we will be notified, and you’ll be released.”

“Well, I’m positive that my bail has already been posted, so can you check in the system and see?”

“Name?” she asked as she wheeled the chair she was sitting in closer to her computer.

“Chelsea Handler.”

“No bail has been posted,” she told me after a couple of minutes. “That doesn’t mean it hasn’t been paid, but it’s not in the system yet.”

“Well, how long does it take from being posted to get in the system?”

“Sometimes a couple of hours, sometimes overnight. The system looks like it’s down. You’re definitely not getting out tonight. You better get yourself a sandwich before they run out.”

I was unsuccessfully trying to fight back tears. I turned to leave and then walked back to the window. “Do you know where I can get some eyeshades?” I asked her.

“Eyeshades?”

“Yes. I need them to sleep. I am extremely sensitive to light.”

“I don’t know if they sell them at the commissary, but you can try. You need to have money in your account, which you don’t have. Once you start working, you will be able to purchase stuff from