When you're the only male in a limo full of fashion models hitting the town to get laid, you don't really stop to wonder how it all happened. You just try and enjoy it. But because you're wondering, I'll fill you in…
A decade or so ago, I wrote a newspaper column in which I tried various tasks I clearly wasn't qualified to do; it was like "Dirty Jobs" meets "Jackass." One of my first jobs was a backstage dresser at a fashion runway show. I got the gig thanks to a recommendation by a model I'd once written about. It also helped that I pretended to be flamingly gay.
Once my inability to identify basic items of female clothing (and my drooling) made it clear that a prank was afoot, some of the models--the few who weren't incensed--admired my chutzpah and invited me out for what was, I assumed, a typical night on the town for them.
Because it wasn't a "typical" night for me, a 5-foot-5 man with no money, I rehearsed pretending to be someone who wasn't impressed with the very real possibility of living out every sexual fantasy he'd ever entertained to this point. I also purchased the most expensive champagne I could squeeze onto my debit card and memorized a set of five specially tailored jokes to fall back upon, in case the evening hit any lulls in laughter or orgasming.
The limo pulled up outside my apartment building. As soon as the driver opened the door, it became apparent that my first role was not stud, jester or even provider. It was errand boy. Anya, a blond model from Poland, had me direct our driver to the nearest gas station, into which I ran and purchased more OJ to mix with the Skyy limo vodka.
The conversation between seven gorgeous models who are good friends was a clusterfuck of namedropping; not just people, but places and fashion terms I didn't recognize. Models are geniuses of a very specific moron world, and trying to keep up felt like being at an adult party when you're a tyke: You try to find some piece of something you can chime in on every five minutes to score a laugh without sounding uninformed. Before we were even halfway to our destination, four of my jokes had been used--to only middling effect--and I had forgotten the fifth.
I'd been to the Sunset Room, L.A.'s club de jour, but not even remotely like this. A huge African-American man, probably the same one who made me wait in line for two hours a month earlier, unhooked and lifted the red velvet and ushered us immediately into the main club, which I mistakenly assumed was our destination. Anya walked us into an unoccupied wing, where a doorway led to a set of stairs guarded by an even huger African-American man.
Upstairs was not particularly nice. It was a well-lit rooftop lined with five or six green tents, closed but slitted slightly open so occupants could see out without being seen. Now I understood about the "no guys." Fresh and well-lit meat was being delivered to whomever lurked behind the slits.
Suddenly, Matt Dillon stepped out to introduce himself. Sort of. He was not particularly nice, either.
"Hey girls, come here," he demanded.
The ladies complied, of course, because "There's Something About Mary" had come out just a few years earlier and Dillon was at the height of his superstardom. This left me standing outside, by myself, next to a cheese tray. As the girls filed in to chat with Dillon, I saw what they didn't: Denzel Washington was emerging from the tent on the right and watching them, apparently cursing himself for not being as quick on the slit. (Little did they know how close they came to spending the evening with the winner of an Oscar instead of a Blockbuster Entertainment Award.)
After my lifelong preference for Swiss was confirmed by sampling all 12 other cheeses, Dillon and a dorky sidekick exited their cabana with all seven of my former models and an apparent plan. Anya saved my evening, and an $80 cab ride home, by motioning for me to follow them down the stairs. I never knew where beyond-hot chicks went when they left a club, but I was about to find out. This time, I was coming with them.
The models went to salsa-dance at a nearby Latin bar called the Conga Room. Dillon and his dorky sidekick were there before our limo arrived. Once again, the ladies and I bypassed the line and were ushered inside. Since Dillon now realized I was an unshakeable part of his model package, he introduced himself to me in a manner that communicated that I have switched entourages. Instead of being in theirs, I was now in his. (This was four years before Matt's little brother, Kevin, redefined the term for a generation.)
To seal this new arrangement, Dillon lit two cigarettes and offered me one. I told him I don't smoke and received the first of many "you're not really one of us" looks of the evening. He handed the rejected cigarette to his dorky friend, who shook his head at me.
Probably the strangest thing about being part of a celebrity entourage was how taboo it was to discuss the host celebrity's career. I discovered this when I tossed out a "Flamingo Kid" reference. Everybody mentioned "There's Something About Mary" to him, so I figured he would appreciate in his newest entourage member having been a fan 15 years ahead of everyone else.
It was at this point that I received the second of those "you're not really one of us" looks. Dillon grabbed one of the models, Dena, and began dancing and making out with her on the dance floor. Dena was half-Irish and half-Mexican. She was married, but she and her husband each had an agreed-upon list of celebrities they were permitted to cheat with. And, so she claimed, Matt Dillon was on hers.
The next memory I have is of being at Mel's Drive-In on the Sunset Strip with the severest cases of hunger and blue balls ever simultaneously experienced by any male in history. Our waiter introduced himself and let Dillon know how much he loved "There's Something About Mary." After dessert, Dillon tried desperately to convince Dena and Kelly to return to his place. But then two female fans who'd been eyeing him all night interrupted.
"Your first movie was what?" one of them asked.
"Great, girls, thanks," Dillon said as Dena and Kelly walked away.
Dillon then applied pressure to another model, one he had barely spoken to.
"Come on," he said. "I know you've got nowhere better to be."
A frustrated Matt Dillon was now scribbling his cell number on slips of a ripped-up takeout menu for all seven models. I was watching the ultimate football captain transform into a standard-issue A/V geek before my eyes.
As anyone who has ever watched video of a lion chasing gazelles knows, you separate out one and you focus. You don't let yourself be fooled by the movements of the entire herd. But guys who have everything handed to them during their sexual lives are apparently not lions. What need is there to develop hunting skills when prey is regularly delivered through stairwell doors and all that's required is the opening of a tent slit?
On the limo ride back home, I asked Dena why she blew off someone on her actual marriage cheating-clause list.
"I decided I don't want to be with Matt Dillon," she said. "It's fun to make out with him because of who he is and what I can tell my husband. But he is so skanky."
What began as my fantasy night, which became a nightmare of watching a celebrity hijack my fantasy, had needle-jumped to the fantasy side once again.
I mean, not that I ever saw any of these girls again. And I'm sure Dillon opened up his black book as soon as we left and made a phone call that insured some action for him and his friend. Either that or he found those other girls and named his first movie.
But at least I didn't have to watch any of that.
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