The Man's Guide to Dating Up
By Tom Chiarella
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Back when I tended bar, I often served couples, obviously on their first date, as they waited for a table. I took care of them, the way a bartender does, and then retreated to wipe down a highball or cut limes, assessing, all by my lonesome, how the date was going. I figured I could learn from it, get better at charming women, even simply speaking to them. That's how miserable I was at dating then, thinking I might absorb something for my own benefit. I didn't learn much - except don't ever look over a woman's shoulder while she's on a date - so I amused myself by developing my theory that always people dated up or down, from one genetic platform to another. It was my own bar game, to figure out how far off the two people were before they themselves even knew.
There were, in the universe I created, no perfect matches. There aren't, on the surface, in any. But for every pair, one of the two people was by necessity "dating up." Usually the man. So I liked to lean on the end of the bar, and determine how far "up" a man could go in terms of whom he'd clamped on his arm for the evening. All this while cutting fruit. So cruel, my assumption that each of us is so limited by the first impression, by what is stock about our appeal or readily apparent in our best efforts. Bloodless. But I was young, I wore a vest to work, and I liked to think I could understand the world in a sidelong glance.
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I was not a big dater. I tended to go home with waitresses, or charm female friends into sleeping with me. And when I did get up the nerve to ask a woman out to dinner, it was generally driven by a hazy enough mixture of lust and expectation that I myself couldn't tell up from down - that is, whether I was dating up or down.
Sometimes it was clear. I once went to dinner with the Miss Alabama runner-up. Another time, I had three drinks with a Division-I cheerleader. I had several dates with a local weatherwoman, a woman who was constantly asked for her autograph although she was only on the air weekends at 11:00. Also, three dates with an all-American gymnast. Dating up. Big-time. So I was wildly attentive, hyper-aware of who was watching us, and snaky with my coolness. Which never really amounted to much, because I left the date that night - or the bedroom sometime later - feeling like I'd been acknowledging only a favor with all my energies. In those cases, I was talking to women who'd never known it any other way.
But I learned: If you can't say that in some way the woman across the table from you is greater than you in some elemental fashion - smarter, sexier, more stylish, possessed of a better body, sweeter eyes, a more natural laugh - then what are you after? What are your ambitions for love? What are you, collecting pelts? Do you think it's that easy? You have to give the higher ground to that which you desire.
Still, never assume the higher ground in love. Never assume you are better possessed than the person you have nudged out into the world with you. Every date, date up. I learned this at every date since the bar, and certainly at every not-date with the beautiful women I have had the pleasure of taking out professionally since then - Halle, Charlize, Brooklyn (although she took me out): Up. This is a form of honor, the representation that something dazzling is before you, or, better, that it's being discovered even as the date dwindles. Accept that you are always dating up. Accept it because humbleness is rare, and rarer still is it so easily earned, with this trick of the mind, driven as a simple assertion of the truth of things: There is no up or down in love.
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And dating down? Do you really thing I would list those women upon whom I made judgment? They're still out there, living lives whole time zones away from my peculiarities. It happened, I guess. But mostly I figured things out way down the road, long after the first date, the first kiss, the first everything - long after I was too deep in to walk away. It had nothing to do with how beautiful they were. No bartender, cutting no end of limes, could have helped me make the call on pettiness, selfishness, pride, greed, or mean-spirited gossip. This stuff always came out later. I only figured out that I was dating down long after the first date.
And the thing is, I'm certain these women would say the same about me, that I'd made them think I was a catch, that they'd been dating up at the very start.
I will say, I once went out with a female bodybuilder who told me as we played pool that she could lift me in a sort of bench press, and later proved it. Beautiful woman, too. Like me then, she drank wildly. I slept with her on the first date, because everything felt right and she seemed so taken with the fact that I said she was "out of my league." If you'd asked me that night, I would have said she was four levels above me, that I was dating up like a madman.
The next morning, I woke up in her bed, hungover and a little scared because, it turned out, she had two young sons, who walked in the bedroom to wake her up to drive them to school. When they saw me in the bed, the younger one, who was maybe nine, just sighed and shook his head. I don't know if he knew I was awake. I don't think it mattered. Nor did it matter that I went out and ate waffles with them, as if the sun came up like this everyday. The boys busied themselves, and watched me, sidelong, like a bartender cutting limes. I knew what they were thinking: I was on the lowest genetic platform just then. I don't know what they thought about their mom. The rankings were moot. She and I were dead-level just then. There is no up or down in shame.
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Photo credit: Bert Hardy/Picture Post/Hulton Archive via Getty
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