Lies That Chelsea Handler Told Me (8 page)

At dinner (food, good; conversation, not so much) Chelsea would bitch about kindergarten, then ask me in front of the whole family if I masturbated. I would bow my head in shame, lie, and say no, but everybody knew I did. We would pass all the food to my dad, and then Chelsea would roll off a couple of jokes, which were funny. Someone would inevitably fart silently, and we would try to figure out who it was, then my father would tickle my mother and blame her. “Oh, Rita, come on,” he’d say with a twinkle in his eye. That usually meant dinner was over.

Simone was the only one who could take Chelsea aside and knock some sense into her. She would share words of encouragement that seemed to have an impact. Glen was good with numbers, so he helped Chelsea with business affairs and taxes. What business affairs a ten-year-old had, I didn’t know and didn’t ask. At a certain point my father had had it with Chelsea, but reform school was out, because it was too expensive.

“Let her do what she wants and she will eventually come around.” That sounded brilliant. Why the hell didn’t he do that with me?

Fast-forward twenty years. I didn’t have a care in the world, and things were going wonderfully. Actually, they were quite pathetic and everyone basically saw that except for me. I was forty-three, a chef, single with no children, and owned 33 percent of a house. The other 67 percent belonged to my sister Shana and her family. The obvious benefit of living together was that Shana’s son Russell had a head that looked exactly like mine, and this caused a few awkward moments when we were introduced to new people.

One day while I was sitting in my third of the house, Chelsea called and asked me to move to LA. “What?” I said. “Are you crazy? The land of fruitcakes and nuts? Why would I leave my happy, pathetic life and move to LA? I love New Jersey and its culture. My whole family is here.”

“I’m not,” she reminded me, Al Capone style.

“No, Chelsea, I can’t do that. My friends, my job, my life is here. I’m not ready for that kind of change.”

“Are you sure, Roy? Your life isn’t really going anywhere. You’re almost forty-five, single, and living with Shana. Obviously, things aren’t going great. If you come out here you could work for me, cook a couple of times a week, travel, and be on the show, which will probably lead to a lot of penetration.”

“Okay. That sounds terrific. When should I come?”

I was scared, but I made the decision, and the rest of the family wished me luck, though I believe I caught Shana giving me the finger as I left. It may have been a wave, but it was very questionable nonetheless.

Fast-forward to California. Chelsea had just broken up with her boyfriend, Ted, rented a ridiculous house in Brentwood, and proceeded to move me, her Pilates instructor, and two Dallas lesbians into it.

“This is your new family,” Chelsea informed me.

I started catering for Chelsea Lately right away. I’d work there twice a week and pick up random catering gigs on the side. Chelsea immediately started putting me on the show and taking me with her on the road on weekends. I was getting more action in six months than I had in my entire life. Before I knew it, my bald head had become the characteristic that separated me from all the other guys on the show trying to get laid. People on the street were recognizing me, I was a burgeoning television star, and I was flying around the country in private jets. I felt like a Rolling Stone, only I couldn’t sing and I was thirty-five thousand dollars in debt. Chelsea eventually paid that off, but not before she took away all my credit cards and told me I should be ashamed of myself.

Chelsea’s quest to find me a little bit of penetration hasn’t stopped since I moved to LA. I appreciate it, but more important, I know better than to get in her way when she is on any kind of mission. I once got between her and a plate of chicken fingers and my finger still hasn’t completely formed back to its original state.

In 2010, Chelsea was the host for the MTV Video Music Awards. Between doing Chelsea Lately, her book tour, and preparing for the VMAs, she had a pretty full plate. She decided that the weekend after the awards were over, she was going to blow off some steam in her favorite place to relax, Cabo San Lucas. I don’t know why she calls it “relaxing,” because as soon as her feet hit the sand she consumes more alcohol than David Hasselhoff at Oktoberfest. It’s pretty impressive what goes down when she has a couple of days off.

Chelsea invited everyone who’d worked so hard for her on the VMAs: her annoying writers, her lesbian stylist, and her semi-bitchy makeup artist. She also took me and her fucked-up book agent, Michael Broussard, who hadn’t done shit for the awards show but was fun to be around and a good backup in case Brad Wollack had too many shots of tequila and tried to put his toe in Chelsea’s vagina, which, by the way, happened again on that trip.

Chelsea’s makeup artist, Gina, and I had become some version of friends. She seemed a little distant when I first met her, which I mistook as her having complete disdain for me, but according to her she’s “been in the business a long time, sweetheart,” and tends to be “guarded.” Whatever… She’s got pretty hair and a plump pout, so I don’t really take issue with her. She fancies herself a green thumb and also thinks she can cook, so I’ve spent a little time with her in both the yard and the kitchen. I’ve definitely seen worse things bent over.

One night while we were in Cabo, everyone got really drunk. Well, that happened every night while we were in Cabo, but during this particular night most of the group had trailed off. Gina had passed out, Brad had facial-ticked himself into a coma, Johnny “The Bird” Milord had finger-blasted some stranger on the couch, and Chris Franjola had disappeared at some club downtown where you could buy sex for less than two dollars. I had no idea where Michael Broussard was, but I do know that one of the resort busboys went missing for three full hours. The only people who were still up and drinking were me, Chelsea, Amy the lesbian stylist, and Sarah Colonna. Sarah may have been in a blackout, but at least she was still sitting upright.

We were staying in two villas: boys in one and girls in the other, although nobody ever slept in their appointed room. As you may have heard, Chelsea has some very questionable sleeping tendencies. Maybe it’s because we have a big family and she’s used to having people around, but she likes to share her bed with random people. When she’s actually involved in a sexual relationship with someone, she prefers that person to sleep in an entirely other state.

Heather McDonald had been studying Gina over the weekend and was working on an impression of the poor girl to add to her repertoire. In case you didn’t know, Heather does borderline decent Drew Barrymore and Celine Dion impressions, and an impression of some poor girl who was popular in the ’80s and had cerebral palsy. I have to say, though, that her impression of Gina was dead-on. Like I said, Gina has been in the business a long time. She likes to talk about movie sets she worked on in the seventies, and she acts as if she’s met every big-time Hollywood person there is to know. I guess at some point in her life she threw a fur coat out of the sunroof of a limo on Sunset Boulevard and told Heather about it.

That night in Cabo, Heather stumbled on to the patio where we were all sitting and was thrilled to share Gina’s fur-coat-limo-sunroof story with us while doing her newfound impression of Gina. Chelsea laughed and then noticed that one of Heather’s eyes was pointing off to the right. Heather is a pretty bad drunk, so Chelsea demanded that she go to bed before she started becoming really annoying. Heather stumbled away on her weird little legs, and the rest of us laughed at her.

“That impression is pretty good,” I said. “She sounded just like Gina.”

“Where is Gina?” Amy asked. “I think I’m sharing a room with her, aren’t I?”

“She’s passed out,” Chelsea said. “You can sleep in my room.”

“Wait, I’m sleeping in your room,” Sarah reminded Chelsea. “Amy can go get in bed with Gina. I doubt she’ll wake up.”

“No, Sarah,” Chelsea said. “Amy can’t share the bed with Gina. Roy has to.”

“What are you talking about?” I asked. “I’m sharing a room with Michael.”

“Not tonight, you aren’t,” Chelsea informed me. “Tonight you’re sharing a bed with Gina.” She went on to tell me that she thought Gina liked me. “She’s always talking about what a good cook you are.”

“That doesn’t mean she likes me, stupid. And, by the way, it’s called a ‘chef.’ ”

“Sorry, that’s what I meant. I mean, you’re a pretty good chef, but you aren’t worth going on and on about the way Gina does. She likes you. She’s alone in bed, and this is the perfect opportunity for you to go in there and bring your relationship to the next level.”

I don’t have a ton of self-confidence, due to the circumference of my head. When someone tells me that a pretty girl is interested in me, even if it’s Chelsea, I want so badly to believe it that I just do.

Since Chelsea’s friends have all been trained by Chelsea, they joined in with her. Amy started saying that she’d noticed Gina giving me the eye a couple of times while we were lounging at the pool, and Sarah said she thought she’d overheard Gina asking Michael Broussard if I had any interest in a long-term commitment. Pretty soon all three of those assholes had me considering changing my Facebook status to “It’s complicated.”

“Roy, go in there and get in bed with her,” Chelsea demanded. “She’ll like it. Every girl loves to be held, especially after a long day of drinking in the sun.”

I don’t drink as much as my sister or the losers she hangs out with, but I’d had a couple of sips of tequila that day, so I was finding what they were saying very interesting. Plus, I hadn’t been with a makeup artist before. I had heard they’re pretty crazy in the sack.

Even though I had already made up my mind to do so, I let Chelsea tell me a few more times to go crawl in bed with Gina. “I expect a full report,” she yelled as I got up and walked slowly toward my newfound lover’s room.

About two and a half minutes later I walked back to the patio to rejoin Chelsea for a nightcap.

“What happened?” Amy asked.

I went to grab a chair.

“Don’t sit down. You don’t get to sit down until you tell us what happened,” Chelsea warned.

“She didn’t go for it,” I mumbled as I ignored Chelsea’s command and sat down.

“What do you mean she didn’t go for it?” Chelsea asked. “We need details, Roy. Let’s get serious.”

I sighed. I was tired, ashamed, and defeated. “I went into the room, just like you told me. Gina was passed out. I quietly shut the door so that I wouldn’t startle her. Then I took off my T-shirt and my boxers.”

“Wait, what?” Sarah asked as she choked on a lemon. “You took off your boxers?” She, Amy, and Chelsea all started laughing hysterically.

“You told me to get in bed with her!” I semi-yelled. I don’t really like to raise my voice.

“I didn’t tell you to get in bed with her naked,” Chelsea shot back. “What is wrong with you?” She then proceeded to laugh harder than I think I’ve ever seen her laugh. “What did she do?” she said, rolling on the patio.

“Well, she woke up and asked me what the hell I thought I was doing. I quickly realized that she didn’t want me in bed with her—even though you told me that she did—so I panicked. I told her I was just trying to get some shut-eye.”

“Some naked shut-eye,” Amy said with a laugh.

“Shut up, Amy. What do you know about sex. You’re a lesbian,” I fired back.

“Roy, please continue,” Chelsea said.

“Well, she told me that she’d heard my T-shirt and boxers hit the floor, which is ludicrous. Pants maybe, but who hears boxers hit the floor? She said that she knew I was naked. She told me to get the fuck out of the room and to stay away from her for the rest of the trip.”

Chelsea was delighted. In her wildest dreams, she didn’t imagine that I would have removed all of my clothing.

“It’s not funny, Chelsea,” I scolded her. “Now Gina thinks I’m a sex offender. We were kind of friends before, and now she probably hates me. I wonder if she’s going to press charges.”

“Oh, calm down,” Chelsea said with a sigh. “I’ll take care of it.” She assured me that she would tell Gina the next day that she had made me get in bed with her. I don’t know if she planned to tell her that the naked part was my idea, and I didn’t ask.

“Thank you, Roy. That’s the hardest I’ve laughed since I broke up with Ted.”

I looked at my sister, feeling glad that I could give her that gift. So what if Gina started carrying a rape whistle around me? At least my little sister was happy. As Chuy so wisely put it once, “When Chelsea’s happy, everybody’s happy.”

“Just so I’m clear,” I asked Chelsea, “do you still think she likes me?”

For the record: my brother is the horniest person I have ever met, and although I find that disturbing, it is one of my great pleasures in life to be a catalyst in his getting penetration.

—Chelsea

BRAD WOLLACK

Chelsea Handler is a hypocrite. The one thing she hates more than anything in life is a liar, and yet Chelsea lies more than anyone else. And not simple lies like “Brad, you were on TMZ last night—oh, wait, it was just a shot of Kathy Griffin’s pubes.” No, we’re talking about emotionally crippling lies.

If she sees your weakness, she pounces. In fact, that’s really the underlying premise of this book. The back cover doesn’t say it, but it should read, “Here’s the deal, Chelsea Handler mercilessly fucks with those around her. They all just have to take it, and here are some of their pathetic stories.”

There are some of us she abuses more than others. Sadly, I’m one of them. It almost feels like I’m a recovering addict. “Hello. I’m Brad Wollack and I’m a constant Chelsea Handler victim.” Chelsea knows all too well that I’m a psychological mess, yet this only fuels her desire to prey on my weaknesses.

Chelsea relishes the emotional strain she places on me when she fucks with me, and, truthfully, she probably doesn’t care. For her, wreaking havoc on my nerves is a good thing. As long as she’s letting off some steam, who cares if I’m contemplating suicide? And if you think suicide is out of the question for me, let me offer you some background…