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“Have you ever dreamt of falling from a mountain straight into a deep hole? Well, I’m about to experience that, and not in a dream. But I’m not afraid, and I don’t want you to worry either. Actually, I am afraid, but I sort of enjoy it too. No, enjoy isn’t the right word — I’m sort of enthusiastic about it, you understand?” — Dmitry Karamazov

In the summer I started dating someone so rich, he has his own jet. And six cars, a motorcycle, two ATVs, and a speedboat. I grew up on welfare and considered myself a revolutionary, of the people. I wondered if he was slumming it with (in?) me. If so, I was castling it with him. His last girlfriend was a model in London. I hate her.

You know the best thing about dating someone rich? He changes for dinner. That’s pretty respectful. It says, “It’s an occasion, to be out and about with you, even if we are just going to the sushi place around the block.” I never thought of it before. I would just wear what I had on that day, from when I went to the beach or whatever. I suppose I did consider it a little: I knew Nazis changed for dinner. So I had a prejudice against the practice. But does not changing for dinner make one not a Nazi? It’s silly and reactionary to live by double negatives.

I dress for dinner now, too.

We met on Match.com. My shrink said I was ready to graduate, with one caveat: I had to try to date someone normal. That’s why I was there. I imagine he was there because he’s used to ordering things online.

I was intrigued by his profile’s talk of name brands, vacation destinations, martinis, technology and velocity (in an ownerly way). He doesn’t say car; he says “Audi TT.” He doesn’t say “not far;” he says “1.6 miles.” Should he ever witness a crime, the detective would lick his lips at the specificity. I would drift into speculation about the criminal’s circumstances and mindset until the guy yelled at me to get the hell out of his precinct.

He was attracted to my profile for the same reason I was to his: “You looked like freedom to me. In real life, too. Always busy with what you’re thinking. You look like you don’t belong, wherever you are. You’re the only person I’ve ever met who doesn’t have an angle, who doesn’t need anything.” He, of course, always looks like he belongs. Everyone in the room turns to look at him — his light eyes, dark hair, good hands; the length of him, the cut of his suit, his graciousness — and something comes over them, something like greed, something like welcoming.

We each left home at sixteen, but he headed straight up, while I wanted to see how far I could burrow into the underground. I’d never even met anyone materialistic before — at least not up close — someone who had chosen not to deal in ideas, which are gelatinous and poofy, but in facts, surfaces. I didn’t know you could live outside of ideas. He gets his hair cut every fourteen days. Me, I’m like Edward Gorey, who refused to mow his lawn because he couldn’t bear to interfere with what the grass and rocks and wildflowers wanted to be.

His cold, dry speech sounded like code to me, and I wanted to crack it. Our first date was at the shooting range. He paused in his activity of removing from a suitcase and gym bag his glock, rifle, pistols, ammo, to take a call to “discuss the significance of operational adjustments on the Net Back to TIP/DBZ.” My stomach about melted down my legs into my shoes at that. I imagined how his accuracy would manifest in more intimate settings.

The first time I saw his place (which was decorated all in black, white, gray, and brown), I thought, “A murderer lives here!” There were no photos, mementos, or quote plaques on the walls. No pen, cup, or any other item that people use in life left on a horizontal surface. If I were to dust for fingerprints, I bet there’d be none. No past, no future. I felt like I was floating in space.

In bed, we discovered how similar were our backgrounds: a dead mom, a dad to whom we don’t speak, and a suicide we believe to have been murder. “Do you ever think about contacting your father,” he asked, “to give him a chance to show you if he’s changed?” I said, “Nah. He’s a sociopath. Those people don’t change.” He plucked from his bedside table a book on sociopaths and read aloud some interesting statistics. He doesn’t read, doesn’t own books (just manuals), so I was surprised that he could reach over and select one appropriate to the current vein of conversation.

“What are you doing with a book on sociopaths?” I asked.

“I thought maybe I was one,” he said.

“Sociopaths don’t wonder if they’re sociopaths — they know. And they don’t care.”

“I’m a little concerned that I don’t have the emotional responses I should to events. Or it comes later, completely out of context.”

“Maybe you’re dissociative,” I suggested.

“I thought about that. Everyone’s dissociative.”

It’s true. Everyone is dissociative.

We started to fool around and stopped, started and stopped. We were sweating, pushing against each other. He tore my nightgown. It was as if we were trying to dig through all this difference between us, down to the spot inside where our mutual history lay, like a miraculous wound that never stops weeping. Things feel like this in the dark.

He filled his (and, soon, our) life with jokes, action-adventure, extravagance, dressing up, front row seats. He threw money. He laughed. I thought he was brave, the way he ignored anything horrible. The one time he acknowledged a problem was when he told me his escape plan, which involved off-shore accounts, unsecured credit and putting everything in my name. This did not look dishonest to me so much as a positive reaction to everything closing in on him. He’d spend two or three thousand dollars on a date to get it just right. We’d go one place for the best dessert, another for the best coffee. Sometimes we’d fly there.

It felt so strange to me, dining on caviar in private rooms, sometimes with his fellow CEOs, CFOs, COOs. The deference of their hangers-on was obvious: a little disgusting, a little addictive. I don’t know why people insist the rich are the same as you or me. They’re not. They move at a different speed, down invisible pathways that open continuously before them. There’s an army of men and women all over the world trying to read their minds, to anticipate and facilitate their every move. We step out of the elevator at the Nine-Zero and the bellboy jumps in front of the automatic doors so we don’t have to wait that extra second to glide through them into my beau’s warmed-up, valet-fetched vehicle, which, due to the turbo-something-or-other and the radar detectors, he’ll push to 120 or 130 miles per hour. Even inanimate objects give way to the wealthy.

The twenty-five-year-old brandy he ordered was made of fire; it circled my lips and moved gently down my throat like a leaf falling from a tree in October. I never had anything find its own way down my esophagus before. Before, I always had to swallow. Lying in his arms later, I felt like that brandy. He was a great choker. Not too hard, not too soft; neither tentative nor so caught up in it as to accidentally cause permanent injury. He just kept me in that starry state the lack of oxygen brings. It’s like being drunk but still aware. (No, it’s more like poppers: the room loomed in and out.) I couldn’t respond sexually because my entire body had gone limp — I had to just let it happen. I studied his every gesture, listened to every word he said. He recounted crouching in wait at dawn for a deer, shooting it, stringing it up between two trees, gutting it. I felt like Mata Hari. Here was a hunter, a polluter, the last of the pure heterosexuals. He would be the first, in revolution, to be overthrown. He was as eager a student of me as I was of him. I introduced him to dadaism, hypnosis, black-and-white movies, humane farming, and the fact — yes, fact! — that, when you really, really think about it, you do not ever have to do what you’re supposed to. Ever.

I took him out on a rowboat, to the beach after dark, to a five-dollar palm reader. I taught him everything that’s useless for societal advancement or financial security, or security of any kind. He taught me about status, the significance of seating order, the debtor mentality, messages in watches. He owns eight. Not Rolexes, because that would be too obvious. His are another brand that costs as much but only rich people know. This way, the clients believe you have the knowledge to be in charge of their millions and do tricks and avoid fraud charges. Because the watches are automatic — supposedly more accurate than quartz — they need to rotate, so he bought a watchwinder. It’s a disembodied wrist that moves in the night. He writes with a $1,400 pen.

He saw my non-attachment to things as freedom. But there’s something static about that lack of desire, I was realizing. Yes, he was consumed with wanting it all, but only to destroy it, then to make his fortune again — make, not keep. He looked magic to me, the way he just leapt and expected the sidewalk to be there to catch him. I decided to be magic, too. When my house sold (my slow investment of the last decade), I decided I’d buy a BMW and just rent a nice place, blowing the whole shebang at once, instead of being dignified and sturdy and halfway safe for another ten years.

One morning, he blurted, “I’m putting all my watches up for sale tomorrow on eBay. It’s all absurd. It’s not real, none of it! Each one of those watches is a down payment on a house. I’ve rethought it all.” I was alarmed. I said, “Don’t sell the one with the antenna!” If you’re stranded on a mountain and your phone gets no reception, you take the face off this watch and unwind a thirty-foot antenna. Two men’s lives have been saved that way.

Perhaps he wasn’t as experienced at trading or merging identities as I was. He’d tell me things he’d never told anyone, claim I had awoken his soul, and then disappear for days, as if to punish me for knowing what I knew about him. I didn’t like to think about what he might be doing out there with his newly awakened soul. We had our first (and only) fight at a Halloween party. It wasn’t even a fight — just a little stirring of revolt beneath the surface. His outfit was a Russian commander with a working paintball (AK-47) gun, which he planned to get people with. I decided on Catherine the Great. I attached a pony pinata to the front, re-enacting her legendary and fictional death under the weight of a rutting stallion.

“Some people are offended by bestiality, just to let you know,” he said. It was a work party.

“Some people are offended by army men killing them, just to let you know,” I retorted.

In his attempt to graft my attributes onto his own belief system, one just would not take: my rabid feminism, which for me was the idea that no kind of sex is shameful and any kind of violence (including psychological, including societal mores) is. This is the unspoken reverse of American thinking in general, and of rich men in particular. I am often inappropriate. That is why he chose me: I don’t fit; I’m not tamed. He wanted me to break him out of his prison of social pressure. He is resolutely appropriate. This is what fascinated me about him. I wanted him to sneak me into the inner sanctum of the winners in this world, the ones with their boots on the heads of the unlucky, uneducated, ungroomed. And now, in costume, drunk as two skunks, we were bristling at getting exactly what we asked for.

Then, the subprime-lending troubles descended, expanded outward. Twelve-hour workdays turned into fourteen. There was no time. One week, our only date was to go into twin sensory-deprivation booths at a spa for a half-hour. Afterward, I got groped in the front seat of his Alfa Romeo for five minutes and he had to take off for a business dinner. On a Saturday. He sent me dire text messages from meetings, referencing various wars and coups, or making fiery-death jokes. He had to fire twenty-seven people in one day, and one of them reached across the desk and tried to strangle him.

Once he left work, he didn’t want to make decisions anymore. “I defer to her,” he said, gesturing toward me when the strip-club bouncer asked did we want a hotel, did we want another girl, another bottle of champagne. “Whatever Lisa wants. Whatever she decides.” He pawed me lazily.

“Hey buddy,” the bouncer warned. “No contact in the private lounge.”

“It’s okay,” he slurred with confidence, “I’m going to marry her. She takes care of me.”

This was true — I picked up his dry cleaning, made his travel arrangements, kept things from him to safeguard his peace of mind. When he’d forget things he’d said or done, I didn’t say, “Hey, you’re having blackouts.” I didn’t even think it. I simply would recount for him what had happened, who said what to whom, so he could get the night straight in his mind. I was holding memories for him.

That wasn’t me. That was what my grandmother did for my grandfather, as did all those 1950s wives. And like those ’50s husbands, he didn’t look like he was falling apart. He always seemed clean and capable. All his shirts were double-starched, all his manners intact; he never left a door unheld for a lady. He was a self-created bionic man. I couldn’t see his stubbornness as in any way incapacitating or isolating. I admired him for choosing to ignore the fact that we’re living in an existential age, to only laugh and imbibe and work longer and harder and pretend his terror didn’t exist. When he couldn’t do it anymore, I took over. I’d stop drinking, or whatever it was he had us doing that night, at one and let him go on until three. I drove us home.

What he was doing to himself seemed normal among all those upper-echelon financial people — drive yourself until you drop, plow yourself down along with everyone else you run over. From what I could see, they’re all on about five different prescription drugs by day and five over-the-counters at night, so they can forget what they do long enough to get three hours of sleep so they can stumble up and do it all over again — finagle all day, both with figures and amounts, and with people’s lives. Keep their house of cards from blowing down. They think they can leave their dishonesty at work, but it leaks into their homes, into their hearts. They’re polluted.

Even in his dreams, he was anticipating disaster, figuring out escape routes. A recurring one was that all the wiring started dripping acid, and no one knew what was happening, and he found the one safe spot, but everyone who wasn’t dead yet rushed him, shoving. He didn’t want to sleep anymore. He called one midnight in a panic. He’d been cleaning and found an earring. He made me describe all my earrings to find out if it was mine. Like they make you do at lost and found before they pass over the misplaced item. As if I would lie and say it was mine when it wasn’t. When I got it “right”, I heard him collapse onto the couch and start breathing okay again. Lately he’d been losing track of time, even when he wasn’t on anything. It was like the sense of time center of his brain was betraying him. He was afraid, with the discovery of the earring, that he’d had an affair and didn’t remember it. We talked about work, the CPA hounding him. He needed to figure out how Enron-like he was willing to go. Should he let the company go down, or risk drowning only himself, or could he find at the last moment some hidden way to make the problem go away? He was thinking, thinking. He’d been putting this moment, and this particular CPA, off for two years, but tomorrow was the day. I was so far away. Our frustration turned into phone sex. I didn’t want to discuss fantasies; I needed to be there. The next day he showed me the PDA-edge-shaped welts across his penis and thighs, what he’d done so I could hear it.

Shortly after that, on another all-nighter, he claimed to recognize me in a porno and showed it to me. There was a series of girls in the video, and he thought I was every one of them, even the Hispanic teenager with moles. He figured I’d altered my appearance for that one with spray-on tan, dark contact lenses and prosthetics. His paranoia had grown slowly enough to acclimate me to it, and it always went away after a while, so I thought this would, too. I thought his delusion was funny, even a little touching: that he would think I was every woman, as if there were no room in his heart or the world of porn for any other. (And that he would think that, at age thirty-eight, I could carry the whole movie.) So I just laughed and said, “Yeah, and I’m sure the director would agree to that. Because Lord knows, people who buy porn don’t want unblemished flesh and bright blue eyes, so he’d be willing to pay a makeup artist an extra $500 to get rid of those for me with dark lenses and prosthetic moles.” Then we had sex, ate breakfast, talked about love and I went home.

That afternoon, he took the porno, a tape of my phone messages, and photos of me — from when we went to a freaking wedding — to some AV guys at a local college so they could do some under-the-table “point-to-point” voice and face analysis. Here’s a man who’s six-foot-two, well-built, sleepless and wild-eyed, flashing a wad of hundreds. What would you have said, if you were those guys? “Dude, it’s obviously her,” they said. That’s what he recited to me. That was his “irrefutable proof” of my “hypocrisy and betrayal.” I had tried to make him think he’s crazy, he said, which was the ultimate manipulation, and he never wanted to see me again. Two days later, he needed to see me again. And I let him. And it was good. And then he did it to me again — he stayed up all night going over a new batch of research porn he’d purchased until he found not only me again, but this time all my friends too, and my house. This time, it was me saying, “I don’t ever want to see you again.”

And I never did — I never saw him again.

The closest comparison to what I felt then happened when my daughter was a baby. Whenever she started crying, I had to pick her up, hold her, nurse her, touch her. Even if she wasn’t crying, I had to touch her. If someone had held me back, tried to stop me, I would have kicked and clawed to reach her. I went from that with him to just nothing. With no warning. It was like someone took a pickax to my stomach and gouged the organs out, and now I had nothing there, just air and some blood.

It wasn’t the sex — I’d had plenty of good sex before. It wasn’t the money — I never accepted anything he tried to buy me: a coat, a purse, underthings, a Mustang convertible. It wasn’t the status. It took about two days to figure out his coworkers were all sleazeballs who spent their time in strip joints lying to their wives and their investors, all of whom were lying right back to them. What made me desperate was that I felt the need to protect him. No one else was, certainly not himself. We spoke a secret language: a system of advance-and-retreat that smart little kids all bent up by circumstances develop and never can quite escape. We understood each other’s senseless behavior; it did not bother.

I too needed what was different between us. He was the key to an unknown world. That I ended up not really liking the world didn’t matter. Everything in my universe looked new when he commented so oddly on it. No one ever made me question my liberalism before; I didn’t even know I was a cliché. This supposedly shallow man made me rethink my every trusted belief, more so than all my philosophy-major, underground-musician, prankster exes combined. I learned that a poor man is simply a rich man who hasn’t been tested. There’s nothing to brag about in having never lived a certain lifestyle, no matter what you think of the lifestyle.

I used to believe, vainly, that this Nietzsche quote applied to me: “Independence is for the very few, [for those] not only strong, but also daring to the point of recklessness. He enters into a labyrinth, no one can see how and where he loses his way, becomes lonely, and is torn piecemeal. And he cannot go back.” But I was never really lost before. I was never lonely. I had my gang of misfits, and my gang of ideas. They evaporated in the hot light of his cynicism. I can’t call him anymore, and my friends don’t want to hear about him or what he thinks — in the end, they decided he’s too cocky, proprietary, doesn’t recycle. Our love affair was a thrilling voyage into hostile territory, and now I’d returned home — to the things I think, to the things I know — and it didn’t feel like home anymore. I can’t make it in his world — can’t afford it for one thing, don’t like it for another — but I no longer wanted to be in mine. Having fallen into a void, now I was lost, now I was lonely. Now I was free.

This article originally appeared in Hooksexup’s Personal Essays.

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