Tasteful Nudes: ...and Other Misguided Attempts at Personal Growth and Validation (13 page)

It was the late ’00s and Myspace was still the social networking site of choice. So, being a man of the times, I had my profile page open in another browser window.

“Hm,” I said, stroking my chin. “I wonder if she has a Myspace page.”

I typed her name into the search window and, as it turned out, this woman (whom, for matters of privacy and respect, I will simply refer to as the Hottest Naked Chick on the Internet), did indeed have a Myspace page. So I giddily sent her a friend request. I wasn’t hoping to establish any real contact with her or anything—it’s just there’s something about becoming Internet “friends” with a woman who really seems to hate wearing clothes that somehow makes you feel more alive. Just ask those nearly four million people who had the same idea with that Tila Tequila lady.

I planned on just getting on with my life after sending the Hottest Naked Chick on the Internet a friend request, but the next day I was stunned to find a comment on
my
Myspace page from none other than—you’re not gonna believe this—the Hottest Naked Chick on the Internet.

“Nice pic of you with Colbert!” she wrote. “Love him!”

As you may have just guessed, my profile picture at the time was of me with Stephen Colbert, whom I had recently met at a comedy festival. Naturally I was stunned. Not only did the Hottest Naked Chick on the Internet actually write me a note but it seemed like we also had a lot in common—like an appreciation of Stephen Colbert to give you just one example.

“This is all happening so fast,” I thought.

I tried to play it cool after seeing her comment, but it was all a bit too much to handle and I couldn’t restrain myself from clicking on over to her page and leaving a comment in return.

“Thanks,” I wrote after a long hard think.

While I was on her page I couldn’t help but notice a few updates since my last visit. Not only had she embedded one of my YouTube videos on her page, but she had also written a familiar name in the “Who I’d Like to Meet Section”—mine. That’s right. Apparently the Hottest Naked Chick on the Internet wanted to meet me, Dave Hill.

Things were officially spinning out of control. And then, before I even had a chance to come back down to earth, I received a full-on Myspace message from—I guess we both saw this coming—the Hottest Naked Chick on the Internet.

“I’m a big fan,” she wrote. “I’d love to come to one of your shows next time I’m in New York.”
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“Whoa,” I thought, momentarily resigning myself to never using the Internet again, as things had fully entered “be careful what you wish for” territory. I suddenly felt like Anthony Michael Hall and that other guy in
Weird Science
, where they just sit there with bras on their heads and the next thing they know Kelly LeBrock appears in her underwear asking if they want to hang out.

“I am officially in over my head,” I thought. “Nay, I am officially in
way
over my head.”

Eventually, however, I pulled myself together and alerted her to my upcoming performance schedule, admittedly something I do whenever someone asks, regardless of age, race, gender, sexual orientation, or whether or not they appear anywhere on the Internet with absolutely no clothes on whatsoever.

“Great, I’m going to be in New York then,” she wrote. “See you soon!”

Strictly for survival purposes, I actively tried to forget the Hottest Naked Chick on the Internet was planning to come to one of my shows in the near future. I was reminded of my date with Destiny (not her real name), however, when, after the shows had come and gone, she sent me another Myspace message.

“Sorry I missed your shows,” she wrote. “I’m still in town. Any chance you would be up for meeting for coffee or lunch today?”

As a Z-list celebrity, I receive requests from strangers asking to meet me all the time, sometimes as many as two or three times a year. Still, it is my strictest of rules to turn down each and every one of those requests. After taking another look at some photos of the Hottest Naked Chick on the Internet, though, I decided to make an exception.

“Absolutely,” I wrote back. “I would enjoy that very much.”

I figured it might be a character-building experience for me, and, perhaps more important, I would get to have lunch with a woman who appears naked on the Internet, which, statistically speaking, is something that just doesn’t happen to most people.

I arranged to meet the Hottest Naked Chick on the Internet at a restaurant near my apartment. I tried to get my friend Meredith, who had stopped by for a visit beforehand, to come with me as a chaperone.

“No way!” she said. “I’m not coming with you on a date.”

“It’s
not
a date,” I stressed to her. “This is research!”

I even tried showing her a bunch of pictures of the Hottest Naked Chick on the Internet on my computer, but she still refused. Weird.

I purposely headed over to the restaurant a few minutes late in an effort to convince myself I was playing it cool, a power move, really. In reality, though, I was struggling to hold it together. Usually when I step out for lunch, I just grab a sandwich or something at the corner deli and head back to my apartment to stuff my face in solitude, not sit down with some naked superfox. There’s just no training for this sort of thing.

“I wonder if she’ll wear any clothes to lunch,” I muttered to myself.

I was starting to feel tingly all over. Also, by this time, at least half of me was starting to think I was about to become the victim of an elaborate prank. But then I remembered I love a good prank, even when I’m the victim.

“I just can’t lose on this one!” I thought.

As I walked through the front door of the restaurant, I braced myself for either outcome. But when I got inside, instead of being greeted by a gaggle of friends laughing, giving me the finger, and kicking me in the genitals (you know, prank fun), I was met by none other than the Hottest Naked Chick on the Internet, who, much to my delight, looked exactly like her photos, which I had assumed must have been pushed beyond mortal levels with Photoshop. Much to my dismay, however, she was wearing clothes—jeans and a T-shirt to be exact. It took me an extra beat to recognize her all covered up like that, but I’d like to think she didn’t notice.

“Hi,” I said. “I’m Dave.”

“Hi,” the Hottest Naked Chick on the Internet said back, shaking my hand.

It was really nice, as if suddenly I weren’t some guy who’s been on basic cable television a few times and she weren’t a woman who hates wearing clothes, but just two totally normal people saying hello to each other in person for the very first time. So we grabbed the nearest table and began chatting.

“I love your comedy,” she said.

“Thanks,” I said, blushing. “I love your, um … you seem nice!”

“Thanks. You too.”

I think I can speak for most straight men when I say this, but—with a few possible exceptions—having a gorgeous woman who regularly takes all her clothes off and lets people take pictures of her pay you a compliment is, well, is the nicest thing that could ever happen. And that alone would have been incredible, so when the Hottest Naked Chick on the Internet continued on in great detail about all the videos of mine she had seen on the Internet, I nearly soiled myself. She even seemed mildly aware that I had been on basic cable television, something not nearly enough people, naked or otherwise, ever seem to notice for some reason. Not only was she the Hottest Naked Chick on the Internet, but it kind of seemed like she was also the foremost authority on Dave Hill in North America. I was dizzy.

“What other stuff do you like about me?” I wanted to ask in an effort to keep her sitting there looking beautiful and talking about my favorite subject.

Ten or twenty minutes later, however, it occurred to me that it would be impolite not to ask her about herself, so I reluctantly changed the topic.

“So what about you?” I asked. “I, uh, notice you, uh, have those, uh, a Web site!”

I felt awkward bringing up the whole naked pictures thing like that so quickly, but it’s not like I really knew anything else about her.

“Yeah,” she said, rolling her eyes. “I posed for those nude photos when I was really young and naive. I regret it.”

“Oh, yeah, I could see that,” I said, trying to sound sympathetic. “Almost made that mistake myself back when I was a younger fella.”

The truth is, I didn’t regret her posing for those all-nude photos at all. How could I? After all, they were what brought us together.

“What I’d like to do is fashion modeling,” she explained as our food showed up.

“Is that what brings you to town?” I asked while picturing all those naked photos of her I’d seen and reluctantly putting clothes on all of them in my head.

“Nah. There’s this other job I do sometimes.”

“What’s that?”

She ignored that last question and turned the conversation back toward me, which I thought was really sweet. But even as much as I loved that sort of thing, I kept wondering about that other job and, what with her being the Hottest Naked Chick on the Internet and all, why she would even need it. After taking the time to field a few more questions about me, I tried to casually bring it up again.

“So, uh, what’s that other job you mentioned?”

“Oh, that,” she said, rolling her eyes again. “You know how sometimes a businessman needs a date for lunch or dinner or something?”

“Of course,” I lied.

“Well, I work for an agency that sets me up with them,” she explained. “I get paid four thousand dollars per date.”

“Wow! Four thousand dollars just to have lunch with someone?” I said, deciding it was best to play innocent. “That’s the best job ever!”

“Sometimes it’s sexual. But only if I want it to be.”

“You’re a straight shooter. I admire that.”

I respected that she played by her own rules. But it also occurred to me that, given the close proximity of our fellow diners, everyone around us was now likely under the impression that I had arranged to meet a prostitute for lunch. She wasn’t dressed like a prostitute, but it doesn’t take a pimp from a
Shaft
movie to figure out that when a woman says she accepts cash in exchange for her company something might be up.

“Wait a minute,” I thought after considering things for a moment. “I
did
arrange to meet a prostitute for lunch.
Awesome.
”

Naturally, the fifteen-year-old in me giggled to himself in a bizarre mixture of mild embarrassment and full-tilt excitement that only a manchild can truly understand. But a moment later, horror set in.

“Oh my gosh!” I thought. “Did the Hottest Naked Chick on the Internet/foremost authority on Dave Hill in North America want to meet me for lunch just so she could proposition me?”

I had never been so conflicted in my entire life: On the one hand, I was insulted that she might think I was the kind of guy who’d be willing to pay for sex. But on the other hand, I was completely flattered that she might think I could afford to spend four thousand dollars on it. Despite my inner turmoil, I did my best to play it cool.

“So, how often do you come to New York to see clients?” I asked now that everything was out in the open. “And how many per week?”

What I really wanted to ask, though, was how she got into it and how did it affect all those other hours in her life when she wasn’t earning four thousand dollars. Did her friends or family know? Was there a special someone out there (you know, besides me) who got to have lunch with her for free whenever he wanted? And did she ever get all freaked out about it like I was?

“But you’re so nice and pretty, ma’am!” I wanted to blurt out. “Why would you do that sort of thing?”

“I want to quit a lot of the time,” she told me, “but the money is so good.”

When I thought about my own hourly rates for my work, I couldn’t disagree. Clearly she had a better agent than I did.

“They’re not even trying!” I thought.

But then she explained, “What I’d really like to do is sell DVDs of me dancing around in sexy outfits.”

I weighed the two options for a moment before deciding that dancing around in sexy outfits was definitely the high road, kind of classy even.

“Now
that’s
an idea I can get behind!” I told her.

She seemed really nice and I felt like it was my due diligence to try to steer her away from a profession neither one of us seemed too thrilled about. Baby steps, I figured.

“Wow, I could be like Henry Higgins in
Pygmalion
!” I thought before quickly realizing I was actually just a jackass.

We chatted for a few minutes longer, mostly about me, but also about her for a couple of seconds, before we finished our food and I flagged down our waiter for the check. And even though she appeared to be the breadwinner between the two of us, I decided to pick up the tab.

“I don’t have to be a john to be a gentleman,” I thought as I considered some of the lessons I’d learned during our time together.

Though there wasn’t any indication that things between us were anything more than platonic (nor did I want them to be, outside of my elaborate fantasy world), I was still a bit anxious as we headed back outside. After all, she was in town on business and Moneybags Hill did just spring for lunch.

“What if she got the wrong idea and still has every intention of trying to book a date with the Big Guy?”
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I wondered.

“It was really nice to meet you,” the Hottest Naked Chick on the Internet said as we stood there on the sidewalk. “Thanks for lunch.”

“Any time,” I replied. “Nice to meet you, too.”

And it really was.

Then I braced myself for whatever might be coming next. But instead of getting down to brass tacks, the Hottest Naked Chick on the Internet just gave me a hug good-bye and walked away. Was I relieved? Sure. But even so, the egomaniacal and wildly insecure part of me couldn’t help but get a little offended.

“What—does she think she’s too good to offer me sex in exchange for money?” I whimpered to myself. “The nerve of her!”

And while, sure, it might have been exciting, titillating even, to at least have been asked, the fact is, if I ever did have a wild time with a prostitute, even a really fancy four-thousand-dollar one, I’d probably cry myself to sleep that night and try to confess the whole thing to every person, house pet, or even lamppost I saw the next day. Call me a prude, call me a cheapskate, call me a self-righteous prick—but I’m just not set up for that sort of thing.