Lies That Chelsea Handler Told Me Read online

  The completion of her bat mitzvah was a miracle in itself. My brothers all had wagers with one another on whether it was actually going to take place. Most kids prepare for a couple of years. Chelsea regularly skipped her sessions with the cantor and rabbi. They had never in all their years at the temple worked with a child like her before. She regularly swore at them, she was always defiant, never prepared, and repeatedly said she wasn’t going to practice until a week before the ceremony. At one point, she slammed down the Torah and exclaimed that all this was practically child abuse, because she wasn’t ready to commit to having a bat mitzvah and wasn’t even sure she wanted to be a Jew. It wasn’t pretty, but in the end she somehow managed to pull it off without making any mistakes. This, of course, drove me insane, as I was silently hoping she would embarrass herself the way she had embarrassed me so many times, but on a bigger scale. Pure schadenfreude. Google it.

  It wasn’t until I was twenty-four that I became determined to repair my relationship with Chelsea. I was single, living on my own in Seattle, and working as a registered nurse. I really wanted to take a trip to Hawaii, and I wanted Chelsea to come with me. Admittedly, I was a bit of a late bloomer, but I was finally ready to sow my wild oats. I thought maybe this trip would be a fresh start for Chelsea and me. We would rebuild our sisterly foundation on a big adventure—just the two of us.

  I very excitedly called her up. “Chelsea!” I said, bursting at the seams. “Let’s go to Hawaii for a few days. I will pay for everything. It’ll be a blast, and I am sure you could use a few days off.” At the time, Chelsea was living in LA with our aunt and uncle, nine cousins, and six animals in a three-bedroom bungalow. She was waiting tables and auditioning in Hollywood.

  My proposition was met with a long silence on the other end of the line. “Can I think about it and call you back?” she asked.

  “Chelsea, really? You won’t go with me on vacation to Hawaii?”

  “Shana, no offense, but you are not my idea of a good time.”

  “I know, but I’m more fun now, and I promise we won’t fight. I’ll even promise to drink with you.” I had never been a big drinker, and Chelsea considered nondrinkers very untrustworthy.

  Finally, she said, “Well, as much as going on a trip with you seems like watching paint dry, I could really use a break. Hawaii sounds pretty good actually. But you’d better cool it, Shana. Your enthusiasm is a little alarming. We are not planning a honeymoon here or going on a bunch of gay tours. I just want to chill out and relax. And drink.”

  “Okay, okay,” I said. Chelsea probably had no intention of doing anything other than getting a borderline amazing tan and hooking up with a semi-hot Samoan dude, but I would try to wear her down. “Chelsea, we can’t go all the way to Hawaii and not even go to a luau. It would be sacrilegious.” I reminded her: “The drinks will be free-flowing, it’s only a couple of hours, and don’t forget, I’m picking up the tab for the whole trip.”

  About six weeks later we took a red-eye flight to Hawaii. On the way, I made friends with my seatmate; she and I talked the whole way there. I knew Chelsea was farting, and I told her to knock it off. Near the end of the flight I got my new friend’s phone number, but when I went to the bathroom, Chelsea ripped it up.

  “What the hell did you do that for?” I said.

  “Well,” Chelsea said, “two reasons, really. Number one, you didn’t shut the fuck up the entire flight. It’s a red-eye, but thanks to you I didn’t get any sleep. And number two is for accusing me of farting on a flight. Shame on you, Debbie. Shame on you.”

  We stepped out of the airport and hailed a taxi. In Oahu, or any tropical destination for that matter, any hotel worth squat is on the beach. I know that now. Back then, however, I thought near the beach was good enough, right? Plus I would save a few bucks. As our taxi started heading away from the beach, Chelsea yelled, “What is happening? We are in Hawaii, I just spent what seemed like four years on a plane, and now the beach is disappearing. Shana! What is going on? Where the hell are we staying?” she screamed.

  “Oh… well, I got a great deal at this place in town. It’s just a half mile walk to the beach.”

  “Oh, that sounds fabulous,” she mumbled.

  We pulled up to the Grand Hotel (not so grand) and I hit the driver with my big tip (not). Later Chelsea lit into me about the standards and practices of tipping. Since she’d joined the service industry as a waitress in LA, tipping had become a very sensitive issue for her. My low tip evidently was unacceptable and not to be repeated. To this day, you are not to argue with Chelsea when she hands you a ridiculous amount of money to give to a waitress, hotel employee, or concierge at a hotel. I’m not rich, and I’d be lying if I said I haven’t thought about pocketing some of the money she’s instructed me to hand out to people on islands we will never see again.

  After getting a few hours of sleep, I suggested we check out the hotel pool. We headed up to the cement rooftop pool and made a quick U-turn. It was not a pretty picture: a bunch of beer-bellied, bald, leering assholes in the Jacuzzi and a pool of questionable water color. Upon seeing all this, Chelsea decided to take the reins on our daily plans. She told me we were hoofing it to Waikiki Beach and to put on my walking shoes. I wasn’t much for exercise or exerting any kind of physical energy, but I agreed, only after she told me my bathing suit looked a little too snug in the rear. Her exact words were “Your ass looks like Delta Burke trying to crawl through a tennis racket.”

  After much complaining on my part and both of us sweating like pigs carrying our crap to the beach in ninety-plus-degree heat, we finally arrived. Chelsea scoped out a decent-looking hotel on the beach with a great pool and a guest population that appeared to be under forty. “Shana, let’s find our spot. Don’t worry, we’ll blend right in,” she assured me.

  “I really don’t know about this, Chelsea,” I said.

  I grabbed two chaise lounges close to the pool, and we set up shop and caught some rays. We got pretty hungry and figured we should try to order some food. I picked out a few items on the menu, and Chelsea signaled the waiter to give him our order.

  He asked for our room number and she blurted out, “Twelve twenty-one.” I, a rotten liar, felt uncomfortable. The waiter looked at the two of us suspiciously but finally walked away.

  “Shana, what’s the matter with you? Just go with the flow.”

  Our food arrived, and a short time later the waiter came back and said that there must be some mistake with our room number. “I am going to have to see your room key, miss.”

  “Oh, I am so sorry, there must be a misunderstanding. Maybe I got the number backward or something.” Chelsea rifled through her bag, as though she were looking for the key. I was shaking in my flip-flops and not being much of a wing woman. Chelsea was going to have to handle this solo. “You know what? I can’t believe it, but I think I lost it swimming at the beach earlier. How about if we just pay in cash?”

  “This pool and bar are for hotel guests only, miss,” the waiter said.

  “Are you accusing us of crashing this pool?” Chelsea said. “I mean, really, I find that very offensive. I am going to have to talk to the manager about the awful treatment we are receiving here.” She probably could have pulled this off, but I had blown our cover. Tears started to well up in my eyes, and Chelsea looked at me with horror.

  “Are you seriously crying?”

  “I’ll be right back,” the waiter said and left.

  “Okay, Shana, let’s hit it. Grab your shit and nonchalantly walk to the beach,” Chelsea whispered. Over my shoulder I could see our waiter with two large security guards on either side of him heading toward our spot. They were both ridiculously overweight, so I wasn’t worried about outrunning them, but I wasn’t fast enough for Chelsea. “Step it up! They are onto us!” They started running after us, but we were able to lose them fairly quickly.

  That was too much excitement for me already, but when you’re with Chelsea, there’s always more to come. We fou