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I recently placed on ad on a hooker site. I hate doing it, but money is tight so I need new income coming in. First, I need to preface this story, well, I don’t need to do anything, but let’s just say that I’m out of practice meeting new clients—the meet and greet. I’ve been lazy in my job search and last night was exactly why.

I was in a really good mood yesterday (although a little nervous). I was having a good hair and face day. Isn’t it strange how one day you can look like a super model and the next like something on the bottom of your shoe? Anyway, I wore a nice blouse, a sexy bright orange lace skirt, and I was strapped with pretty new heels. I felt like the perfect mix of sensual sophisticated. My tits weren’t falling out of the top, but I try not to scream hooker when I meet these guys. Plus, most dresses/tops that have massive cleavage plunge are tight around the mid-section and that’s my problem area. However—as my mom was kind enough to point out recently—I can sometimes look bigger than I actually am in the flowy tops. But if you’re a woman with large natural breasts and a poochy stomach, you understand the comfort of a flowy blouse.

Four o'clock came around, and I drove to Marina Del Rey. We were set to have a drink and maybe more if all went well. He said I should bring stuff to spend the night. Yeah, right. I didn’t tell him that there was no way in hell I’d be sleeping over, better to discuss these things after wine and a blowjob.

I parked and text that I had arrived at his building. He said he was going to bring his puppy. I thought that was a sweet idea. I saw him walk out of the monolith condo building. He looked exactly like his photos. 50’s, chiseled features (bordering on odd, but interesting). He wore jeans, a button up shirt and sports coat: classic “john” apparel. The puppy was over-the-top cute. Huge paws. He looked like the dog version of my Maine Coon cat.

About five minutes into the date (as we walked to the restaurant on the lagoon), I liked the puppy more than the man. I think he knows this about himself. The dog got loads of attention, while he was awkward at best. We arrived at the restaurant, and sat at a table on the patio. I ordered a Pinot Grigio. He ordered the house merlot, which I unenthusiastically noted. House merlot? Who the fuck orders house merlot?

Anyway, we talked. The conversation was stiff. He had a lengthy bio on the website: about how he comes from old money and has been to every country, and that he was a monk for fifteen years. He also mentioned a reality show about a guy who searches for oil. Something like that, I honestly couldn’t give three shits. I thought for sure that with all that life experience, we’d have tons to talk about. But he was a tough kernel to engage with. Thank god he brought the puppy. That puppy is his personality! The man was fairly mute. I guess he got that part of monkdom down.

I was struggling—and way too sober. I can usually talk to a tree better than this guy! I don’t know what was up with me. We managed to make it through our wine. I even got a smile out of him at one point. The waitress came around and before she could ask us anything, he requested the check. I figured we were done. I got the feeling I had a better chance of fucking the dog. He paid. I thanked him. We walked back. We got to the crosswalk, I was getting ready to say, “It was nice to meet you”, when he asked if I wanted to come up. I was genuinely surprised. This was not a man who acted like he wanted up my skirt. He seemed like a man who wanted to set my skirt on fire. I should have left, just thanked him and driven like an old bat outta hell, but I didn’t because this old bat needs money and a new client. So...I said sure.

His apartment: small one bedroom with “A view”, as he pointed out. The front door opened into the kitchen area, which was filled with boxes. Semi halting. First thought; “Are those filled with hookers past?” The place was decidedly unimpressive. Not only did it not look like a place a man with loads of money lived, it didn’t look lived in at all. Was I being punked? Or a soon-to-be cautionary tale? He asked if I wanted wine, remembering the merlot incident, I said sure and that red would be fine. As he poured the wine, he said something about moving to Santa Monica (hence the boxes). Sure, dude. So many things were going through my mind: does he really live here? Is this someone else’s place? Or is he married and this is his fuck (or kill) pad? Like Dexter, but with no code. I didn’t let any of these thoughts marinate though—I’m good like that. Instead, I used the bathroom and text my friend to let her know I was alive.

When I came out, I took a seat on the couch—besides the coffee table, the only piece of furniture in the small living room with the view. He had lit two big scented candles, presumably to cover the dead hooker smell. Then he played some fantastically cheesy opera music from this strange little system in the corner of the room with a screen facing inward. I mentioned the weird set up he said nothing. That alone should have had me leaving. Fuck the boxes...was he filming this? This idea didn’t really hit me until after I left. My eye was on the prize at the time. Prize, Ha! Nothing about this scene felt hopeful or prize-like, but I was there, and in super sweet mode.

The music cracked me up. It was the same soundtrack that was stuck in the cassette player of the rental car I had in Tuscany circa 1997. So. We’re on the couch drinking his two-buck chuck—yet another bad sign on the “I’m a millionaire” front—and he’s sitting a few feet away with zero positive body language. We clinked glasses. No, I didn’t watch him pour it to make sure he didn’t drug me, but honestly, my body is fairly impervious to poisons.

My pretty woman dreams were sailing away. Did I mention that over his house merlot he told me he owned a yacht and invited me on it once it was out of the yacht shop? Again, sure dude.

Back on the couch: This guy was as cold as deli meat and his puppy was biting me. The dog was adorable, but come on, he smelled like sadness and lagoon condoms, plus he was tearing my skirt. I thought, “Is the puppy some kind of test?” If the dog likes me, the condo opens up into a palace filled with buckets of cash? Yes, this is what goes through my mind. Not, am I about to be deli meat? So I was nice to the dog. His owner was giving me the stink eye and less than zero sexual energy. Jesus. This was going nowhere slowly. Snap to it, girl!

I leaned over and kissed him. He was a decent kisser, which surprised me, but it was clear he wasn’t enthused. The only happy thing in the room was the puppy—who was probably giving me rabies. Mr. Silencio was giving me absolutely dick all to work with. So, in the most uncomfortable manner possible, I said, “Honey... so...if we are going to go any further, I will need compensation.” This is my very least favorite part. This is why prostitutes have it spelled out in their ads: “Have the money ready for me on the side table”. I’m an idiot. He wasn’t making it easier. He looked at me like I just snatched one of his kidneys without novocaine. You know the drill, asshole, why are you making me out to be some kind of monster? He mumbled some sort of OK, that he had money. It was so torturous. I wanted to save him the time and put myself in one of those boxes. Or swan dive off his lovely view. The music was perfect for a swan dive. Found dead on sidewalk: “35” year old Jane Doe in a pretty orange skirt.

At least the bed was cozy, but he lay there like a skinny, annoyed log. You would of thought I just told him to fuck his mother. Why do I do this to myself? It was officially the strangest first hookup I’ve ever had...and I’ve had a few thousand.

I kissed him. Not much back. So I just held him and sort of felt my way around his jeans, looking for any evidence of life. I cannot tell you how motionless this guy was being, like he was playing dead. Did he expect me to jump his bones like this? Maybe he can’t get it up and was really just looking for companionship and I “ruined” it with the money talk. Perhaps that’s what his dog was trying to communicate to me.

I decided I would show the monk my spiritual side. I can be still, too. I laid my head on his chest and we lay there listening to the mid-life music and times past. I don’t know why I was trying to impress this guy with my ability to be quiet. It was torture. How long should I lay there? This is why meeting guys at the strip club was so much better. There was a rapport, they saw that I was sexy, and they desired me. Also, we could negotiate the fee over loud music and marshmallow-scented flesh. Perhaps twelve minutes passed when I gave up. I sat up. I laughed at myself, and the situation, and said, “Ok, honey, I think I should go.”


I put my heels on and left. He half walked me to the door and made like he was going to walk me down, but I said it was fine. I knew my way out. I walked to my car feeling like a world-class idiot: a smooth-skinned, ho-smelling jackass. I drove home and took pictures of my clean-shaven twat for a boy I’ve been flirting with. That was that. You win. You lose. Or so I thought.

I took my heels off and offered that we go to the bedroom. I wanted this shit over with. Again, he seemed bummed at my suggestion. I was at a total loss. His bedroom consisted of a bed and not much else.

I woke up in the morning to sweet messages from the boy. I was happy. I got online and discovered that the winery in Calistoga who had commissioned a photograph of mine to be on a small batch of white wine was finally out. I had a new found sense of hope...and then I hit refresh. An email from Mr. Wonderful: “Thanks for coming over, perhaps if you lost a great deal of weight, we could start something. In the interim we can be friends.”

There went my glow. So many things went through my mind. First, I used current photos on the site (although, yes, I’m a photographer and I know angles and how to capture my assets and hide my flaws), and second, I put myself in the “Curvy/Voluptuous” category. Hello! I could have chosen “Athletic” or “Thin”, but I’m not trying to fool anyone (with exception of the age) and was specifically trying to avoid this sort of thing. I’m not skinny anymore. I have big natural breasts, long thin legs, and some lumps...can that be a category, “Thin and Lumpy”? How about, “Not bad for a lazy ass forty-five year old”?

Here’s the thing, no one wants to get an email like this. It was completely cruel and unnecessary. Did he really need to go out of his way to tell me this? Easy as pie to just never contact me again. Which I’m sure he hasn’t eaten since 1982. I hate manorexic men. Friends? Is he joking? Yeah, buddy, let’s be friends. Fuck off. I tried to let it go, but I’m human and it effected me. Of course this would have to be my first experience out of the gate. I group text my homegirls, they were aghast (God bless their souls). I joked, “Maybe I was too big for him to chop up and fit into his freezer.” My friend Elizabeth replied, “You’d be too large a skin suit.” “Exactly, I’d be too baggy for his tiny frame.” Maybe I should thank my lucky stars for my extra poundage. Maybe I wouldn’t be here at this bar writing and downing vodka soda’s if I were skinny like the old days. I guess I need to rethink my outfit for next Wednesday’s date. I hope he's fun and doesn't wanna play dead.

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