Life of the Party: Stories of a Perpetual Man-Child

by Bert Kreischer

We saw the two dorks that had taken the boat to the island with us and matched their fake hellos with fake hellos of our own. He was dressed in a suit with a bow tie and she was in a dress just shy of an evening gown. I played a little mental game that I often play called What Do They Look Like When They Masturbate. It’s a fun game to play, especially in a room like that. And for him I envisioned it perfectly. His masturbation was something he succumbed to and didn’t delight in. It was fast and necessary, filled with guilt. His secretary had a slip of the nip and he couldn’t control it, and when he was done there was a harrumph, as if he’d let himself down. She on the other hand didn’t masturbate at all, as she was averse to pleasure, thus explaining her marriage to him.

  We were seated outside and as soon as we arrived at our table, a Key deer walked up to greet us, as if it had been cued by the hotel staff. But it wasn’t. LeeAnn lost her fucking mind and started feeding it, which apparently was something everyone had already been briefed on. They stared as if LeeAnn had started shoving the cutlery up her asshole. An older woman quickly reprimanded us, saying that we were not to feed the deer under any circumstances. What other circumstance would there be, I thought to myself, other than one just walking up to us.

  “How can anyone not think that a small deer coming up to your table and wanting a snack isn’t an absolutely amazing life experience?” LeeAnn said to me.

  I ordered a bottle of wine—with one glass—and we did what most couples do on dates: We eavesdropped on everyone else’s conversations. Our food arrived and shortly after, we heard the woman who had reprimanded us ask to speak to the chef. The waiter obliged, and LeeAnn leaned in. “This can’t be good.”

  “You think she saw him feed a deer?”

  When he came out, she said five words while pointing at her plate.

  “You are better than this.”

  I’m sure the chef had a bunch of words himself that he’d like to share with that lady, but he apologized and promised a better meal the next day. LeeAnn and I were appalled but were too busy wolfing down our meals to be bothered with whatever small detail in the recipe that had pissed her off. So when the waiter asked what we thought of dinner, we told him that the woman was out of her fucking mind, and the meal was possibly the best meal we’d ever had. And it was. Everything there was mind-blowing. The wine, the views, the service, the privacy.

  But the people that were vacationing on this island could suck hot homeless dick for all I cared. I’m not sure if it was because we were outsiders, getting all of this opulence at a discounted rate, so we were easily satisfied. But it seemed that everyone we’d run into was more disgruntled than the last. I’d never paid four figures a day for a room (I still haven’t), so maybe being an asshole just comes with the territory. I’d probably be pretty pissed off, too, if I knew that every moment of a vacation was putting me deeper in the hole. Anyway, that wasn’t the case for us.

  After dinner we retreated back to our cottage, I took another outdoor shower, and LeeAnn filled out our breakfast menu for the next morning.

  That next day the most amazing thing happened. We woke up comfortably around eight o’clock and I heard a noise on the front deck. I opened the door and saw what I thought was the same Key deer scamper off the deck and down the steps. In front of me was a table set for two with breakfast waiting for us. I swear to God, it was like the deer brought it to us, walking on his hind legs, holding it on his head and front hoofs. I told LeeAnn breakfast was outside and she couldn’t believe it. We walked over in our robes, sat down, and to my astonishment, it was piping hot. To this day I have absolutely no idea how they did it, but every single morning, the second we’d open the door, breakfast was waiting for us at a temperature that suggested it had come directly from the kitchen. And every single morning there were Key deer watching us like the Little Rascals, waiting for us to slip up and leave our meals unattended just long enough for them to snag a bagel. We finished our breakfast, got dressed for the beach, and headed in that direction.

  We were the first ones there that morning, but to our confusion every single chaise lounge had someone’s bag on it. Every chaise lounge except for one. Not a single soul was on that beach, yet every single seat had been spoken for? These fucking disgusting rich people, we found out later, would wake up at five in the morning, claim their spots on the beach, then go back to bed and come back when they were comfortably rested. It absolutely blew my mind what these rich fucks were capable of. Is this the behavior you have to assume in order to amass millions? When they started showing up around ten o’clock, I saw that the woman who had claimed the most chairs was the same woman who had chastised the chef the night before. I wanted so badly to walk over to her and say, “You’re better than this.” But the truth was she might not have been. I gave LeeAnn the last seat, and I stood in the water with a Gumby Slumber, staring back at my wealthy neighbors.

  And that was how just about every single day went down. We would get down to the beach earlier and earlier, still to find only one seat available. As people showed up I would try to guess which bag matched their outfit for the day and guess which seats they had “called” before sunrise. I would be left standing in the ocean, facing everyone with cocktail in hand, telling LeeAnn stories, while everyone eavesdropped. As the week passed, it seemed more like I was doing stand-up for the group than talking to just my wife. Until one day everything changed.

  Halfway through our stay, a thunderstorm of a man and his lightning rod of a girlfriend showed up on the beach. They looked to be straight out of the Sopranos. He was a large man with tattoos in places so odd I thought they must have been earned rather than bought, while she had the unmistakable figure of a onetime stripper. The first morning they came to the beach, LeeAnn and I were already there, but the others hadn’t arrived yet. He looked around and saw that every seat had bags on them, and with a shrug of his shoulders and a “What the fuck” muttered under his breath, he threw the bags off of the chairs he wanted. Come ten o’clock when the woman who had chastised the chef (every single night now) found her stuff lying in the sand, she asked the group, passive-aggressively, “What happened to my bags?”

  The man looked her straight in the eyes. “They were on my fucking seat.”

  “Oh no, you’re mistaken, sir. We called those seats.”

  “Doesn’t look like it’s working out so good for you.”

  “But we woke up early and put our bags on those seats so we could have them.”

  “Take that shit back to Connecticut, honey. What you think this is, high school? When I’m done with my book you can have your seat.”

  And that was that. There was no more calling seats after this man arrived.

  My stand-up got a little louder each day, as I stood in the ocean facing LeeAnn and hoping to God this guy would recognize just how funny I was and take me under his wing. I wanted this guy to like me more than anything in the world.

  Until this point, LeeAnn and I felt like the black sheep, but now that these two were here, we were in the clear. He would sit on the beach in black shorts, a black Tommy Bahama shirt, black sunglasses, and a black hat while his chick downed champagne in a skimpy bikini, tearing through Marlboro 100s. And in some sort of Darwinian turn, the disgusting rich-people tribe started to warm up to LeeAnn and me. It was hilarious, watching them try to connect with two people they had turned their noses up at.

  One of the women handed LeeAnn a James Patterson book, The Big Bad Wolf, while I was at the bar. “I got this for Bert.”

  “You got Bert a book?”

  “Yeah. I thought he might enjoy reading a book on the beach like the rest of us.”

  “Unless it’s got rum in it, I don’t think he’s going to touch it while he’s here.”

  When I got back to the beach with another drink, LeeAnn was forced to tell me about the present the woman had gotten me, in front of her. She couldn’t keep the laughter out of her voice. “Bert, this lady was nice enough to get you a book.”

  “Wh
at for?”

  “I think she wants you to read it.”

  We held in our laughter. We were like two kids who had just smoked weed before study hall. I thanked the woman profusely and poured on for over an hour about how much I loved dogs. You can imagine my embarrassment when later I found out that the Big Bad Wolf was a serial killer and not a canine.

  As the week carried on, I got no closer to meeting the two people we had now found were named Danny and Dawn. We’d see them at the beach, and I’d passed by them on the way to the bar, trying to get Danny interested in me with some witty one-liner or a comment about how nice the island was, but like I was a fat chick on spring break, not once did he even notice my existence. Our second to last day, we took a boat ride with a new young couple. It was a sunset cruise, the martini of boat rides, and they were actually fairly decent people. They were our age and, from what I could gather, he came from money. He and I drank on the boat like pirates trying to get rid of the clap, as the captain sailed us around the island. We watched the sunset, and on our way back in, began talking about the mystery couple. They, too, had noticed Danny and Dawn and had been just as fascinated as LeeAnn and I were.

  “He’s got to be in the Mafia, right?”

  “Definitely,” I said.

  “Do you think those tattoos mean anything?”

  “They have to. They are in too odd places not to.”

  “You talk to everyone; what is he like?”

  To their dismay, and my own, I explained that I had not been able to break the ice with this man the entire trip and I had absolutely no idea what he was like, beyond standoffish, overweight, and banging a hot stripper. We spent the rest of the ride back to the island fantasizing about what their lives must be like back home.

  We got back to our cottage and I took yet another shower. I was finding so much enjoyment in that shower that the treetop animals must have thought I had OCD. We went to dinner, we came back, I took another shower, and we went to bed.

  The next morning was our last full day on the island and much to my chagrin, Danny and Dawn were nowhere to be seen. I spent the day like I had spent the previous five, standing in the ocean, drinking the signature drink of the island, and working on new material to the crowd of eavesdroppers. That night, LeeAnn decided she was going to allow herself a glass of champagne, so we found a couple of Adirondack chairs on what we thought was a secluded part of the island, facing the sunset, and we ordered an expensive bottle. Just as we opened it, Danny and Dawn came walking up behind us on their way to the dock to take the boat ride we’d taken the day before. As they passed behind us, I shouted to them, “Boat ride?”

  Great opener, Bert. State the obvious, pose it as a question, and open your eyes real wide.

  They said nothing and kept walking. My first attempt failed, but I knew for a fact that when they were done with their boat ride, they would have to walk past us one more time. We sat and drank champagne and I planned my attack. We saw the sunset, I killed most of the bottle and switched to beer, and by the time they walked back past us, I was well lubricated, locked and loaded with a better intro line. When they were the perfect distance away, I perked up out of my Adirondack chair like a gazelle who had just heard a lion fart, and I motioned to them.

  “Hey guys, come on over and have a drink with us.”

  They said nothing. Assuming that they didn’t hear me, I tried again.

  “Danny, Dawn, come on over and have a seat and a cocktail with us.”

  I saw the look on Danny’s face and realized that there was no reason why I should know their names.

  “Do I know you?” he called out from twenty feet away.

  I was busted. I looked like a stalker now—or worse, an undercover cop. Picture me on my feet, holding a beer, in board shorts and a tank top, a look of dumb shock on my face.

  “No, I’m Bert and this is my wife, LeeAnn. We were just wondering if you guys wanted to sit down and have a drink with us.”

  Danny stayed back, dressed in the same black-on-black beachwear he had been wearing all week. “We’re good,” he said curtly.

  And they left. I felt like a complete and total asshole, but at least I had given it my best shot. As we headed back to our bungalow, LeeAnn and I imagined what the night might have been like had we hung out with them. We got back to the cottage, LeeAnn began to get dressed for dinner, and I went to do the thing I loved doing most on that island, namely, taking an outdoor shower. My genitals by this time had been washed red, my hair turning brittle, my feet forever pruned. I was shocked when LeeAnn came out and stopped me before I could get in.

  “Danny and Dawn invited us to their room for drinks before dinner.”

  “What?”

  “Dawn was just standing outside our bungalow, shouting for us. I went out there and she said to come down immediately, they were ordering cocktails for us.”

  I quickly threw on the clothes I had been wearing and we made our way to their bungalow. When we got there, we were stunned. It was three times the size of ours, two stories, hanging over the water, with a dock surrounding it. Mob money must be slamming, I thought to myself. Their bungalow was also easily three times more expensive-looking than ours. When we got to their door we noticed their names weren’t on it.

  “Typical Danny. He likes his privacy,” I said, as if I had known him my whole life.

  “I know, right?”

  We knocked on the door and Dawn greeted us in jean shorts and a bikini top.

  “I’m fucking so glad you guys could fucking make it. Sorry about Danny earlier, he don’t fucking like nobody.”

  From the background we heard Danny yell, “No, I just don’t like the fucking people on this island.” Danny then appeared from one of the many rooms in their bungalow in a wifebeater and his black shorts. “They’re all stuck-up cunts if you ask me.”

  Wow, I thought, we are getting to see Danny be Danny. It was like going to a wedding with Sammy Davis Junior and watching him dance drunk.

  He stuck out his hand. “I’m Danny, this is my chick, Dawn.”

  “I’m Bert, this is my chick, LeeAnn.”

  “I’m his wife,” LeeAnn corrected.

  “My first wife.”

  Danny let out a roar of a laugh, put his arm around my shoulder, and walked us into his living room.

  “I told the bar to send over whatever the fuck it is you’ve been drinking all week.”

  I looked over and saw a spread of booze that looked like it belonged in the Puff Daddy suite. Two bottles of Cristal on ice, a bottle of Johnnie Walker Black, beer on ice, wine opened and breathing, and pitchers of Gumby Slumber.

  We sat down and Dawn poured us all drinks.

  “No, thanks,” LeeAnn said.

  “You don’t drink?” she asked.

  “No, I do, but I’m pregnant.”

  “Oh, how long have you guys been a married?”

  “Five days,” I said.

  Danny started smiling. “You guys ain’t like these fucking people at all, are you?”

  “No, we are not.”

  LeeAnn looked at me. She could hear my accent shifting into Danny’s as I matched him in tone, energy, and personality. I tend to do that from time to time, mostly around black people.

  “How you fucking affording this?” he said.

  “My dad got us a deal.”

  “Ain’t no deals on this island, kid. Everything’s overpriced and everything has a price tag on it. What do you do?”

  “I’m a comedian, she manages an apartment building.”

  “Real fucking people, I love this. A comic and a slumlord.”

  Dawn popped a bottle of Cristal and poured me a glass, and despite the fact that I was already holding both a Gumby Slumber and a beer I had brought from our room, I gladly accepted it, as I figured this might be the only time I would ever be able to drink Cristal.

  She looked to LeeAnn imploringly. “Are you sure? It is Cristal.”

  “If there’s one thing I know about Le
eAnn, it’s that she loves champagne,” I said.

  “It ain’t gonna make a fucking difference to the baby; my second wife drank a glass of wine every night when she was pregnant,” Danny said.

  Sage enough advice for LeeAnn, I guess. “I’ll have a small glass,” she replied. We all smiled.

  We got to know each other. Danny was in the concrete business. He told us he’d been “pinched” in a town very close to where LeeAnn grew up, which confused my literal wife. “Who pinched you?” “A cop,” Danny said flatly. “Why would a cop pinch you?” Danny almost laughed the tattoos off his plump frame. Danny never said anything about the Mob or being in the Mafia, which only fueled my speculation that he was. As I kept drinking, I saw every detail of his life through my Mob glasses.

  Dawn, despite having the body of a stripper, had children almost our age. She steered the conversation all over the place, hopping from subject to subject at high speeds. She mostly talked about her psychic abilities and the fact that she knew our child was going to be a boy and a Gemini (it was neither). I talked at great length about myself, and Danny seemed sincerely interested. He loved comedy and loved the fact that I knew the material, off the top of my head, of all the comics he loved. I was so excited to be hanging out with them that I wasn’t paying attention to what I was drinking, or how fast I was drinking it. While LeeAnn kept the same small glass of Cristal in her hand, I was juggling beers, champagne, rum, and now Johnnie Walker Black like a bear in the Russian circus. We talked so seamlessly and effortlessly that we didn’t realize how much time had passed until Dawn looked at her watch.

  “Oh shit, we’re gonna miss dinner.”

  “Fuck it, let’s go. You guys want to eat with us tonight?” Danny said.

  “Sure,” I said. “We’ll go down and get changed.”

  “Fuck that shit, were going like this.” Danny stood up. If Danny wasn’t concerned with the dress code, then neither was I. I looked to LeeAnn, who shrugged her shoulders.

  “Fuck it,” she said.

  There are three moments in my life, now as a forty-year-old, that I wish had been videotaped. My first home run. The first time I did stand-up. And the moment, that evening, when I walked into a five-star restaurant with Danny, Dawn, and LeeAnn, wearing board shorts, flip-flops, and a tank top. Slow motion, a mismatched foursome who looked like they were straight out of Daytona Beach central booking. Oddly enough, I was the nicest dressed of the bunch. LeeAnn was in little more than a cover-up, from having been at the beach all day, Dawn was still in a bikini top and jean shorts, and Danny was wearing black shorts, a wifebeater, and house slippers. Before the maître d’ could say anything to us, Danny slipped a hundred-dollar bill in his hand.