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Older member of my extended family asked whether I was ever going to date again. I was brutally honest and said I don’t know, probably not, and they were troubled by that answer, and then we went a few rounds of whys and wherefores.

Here’s the thing.

I’ve been in a larger number of legitimately long-term relationships than most people have, I think. I started almost right away. I’ve had five relationships in my life that went at least a year. Four of those went at least two years. Two of them went five years or more.

All of them started wonderfully, and ended miserably.

— § —

In my early ’20s, I wasn’t established yet, but for a young twentysomething, I don’t think I was a bad catch. I had done TV interviews about science on the evening news, had entered college early at 15, was technology expert who also studied human culture. Very well read. Had stock options, my own car, a steady job as an editor, and plans to go to grad school. And I was six feet tall, slim and muscular, not bad looking (I wistfully say now, looking back), and not at all a geek. Other young people called me a ‘rock star.’ Not just my professors, my peers.

At the start of that relationship, she was “so lucky” to be in a relationship with me. And for several years, it was like a match made in heaven. And then it wasn’t. Over time, I was compared to other people, and found to be lacking.

Thing is, no matter how hard you’re working, no matter how ahead of the game you think you are, there is always somebody who’s going to out-play you, out-look you, out-tall you, out-hustle you.

I was out-hustled and eventually, cheated on and left.

— § —

Big interim, let’s skip to me as I entered my 40s. Double bachelor’s degree, master’s degree from the University of Chicago, Ph.D. from a legendary school in Manhattan. Seven books to my name. Ten years as a professor, then a pivot to private industry where I became a technology industry executive with a strong career. Unusually well-read, literate, even, yet down to earth, decent conversationalist. Still six feet tall, still not some awkward geek.

Still getting called a loser who will never amount to anything and routinely compared to other guys who have done more. This guy founded a company that became a hot startup. That guy traveled the world and has lived on multiple continents and speaks five langauges. I just don’t match up, such a mistake to settle for me when men like them were available. When will I earn a quarter of a million? When will I become a CEO? Obviously no ambition. Loser.

— § —

It generally has always gone the same way. Great start, then a pivot somewhere over a middle period to “why did I settle for you?” And then dissatisfaction. Nagging and bitterness. Eventually a period of deep and bristling contempt for me. Then end.

Yet I have never cheated on anyone in my life (though I have been cheated on multiple times). I have never forgotten a birthday, an anniversary, a Valentine’s day. I have taken people on dreamy road-trip dates to restaurants a thousand miles away and to Radio City Music Hall and Carnegie Hall on black tie dates. I do housework. I am thoughtful. I write notes. Not because I think I have to, but because I want to. I have myself actually yelled at a woman maybe twice in my entire life. I’ve never hit one. I don’t call people names and it’s not in my nature to do so. I’m easy to get along with—so long as by “get along” you don’t mean “Aron has to do what I say he does and make the choices I say he must.”

Still, by the end, there is always someone (or someones) that I just don’t measure up to. The grass is always greener somewhere. Well, yes. It is. I’m a solid performer—recall, masters and Ph.D. from significantly brand-name schools, VP in technology, seven books, six feet tall, holiday-rememberer, dishes-doer, romantic dater, reasonably masculine (or, when being lambasted, “so unapologetically guy”)—but still that’s all it is. No, I’m not a founder and CEO. No, I do not earn half a million a year or have 10 million in my 401k. I don’t drive a late model BMW. I don’t have a rolodex that stretches to the halls of political power. I haven’t run for elected office (yes, this comparison has been made in my life, and I have lost out to the guys that have).

And in the end, it’s miserable. Not only because I don’t compete at that level, but because I don’t want to compete at that level. I’m already too posh for my own comfort. I was raised a lower middle-class kid, with TV sitcoms and clutter in the kitchen. I don’t want to stray too far from that because I like it. It feels like home to me. I don’t want to live in an immaculate architect-rendered house with an atrium and a Zen garden and snap photos of us in the sauna for Instagram. I just don’t.

— § —

Older relative says there is someone out there for me, I just have to look, it’s important that I not be alone.

Maybe, but I don’t care. I’ve done the long-term relationship ending in a painful breakup where I’m just a loser by comparison too many times. I’ve been cheated on, yelled at, belittled, even belittled in public while standing next to other high-achieving guys. It’s a whole bunch of no fun.

All of this was too much to try to explain to my older relative. He’s from another time and genteel as they come. But the thing is, I just don’t care to do it again, to keep looking. I don’t care to try to compete again. A Ph.D. and a pile of books is enough for me. I’m done questing and conquering. I’m almost 50 and I’ve been at this life thing for a long time, and been through too many “hell-like final years” during which I was beaten over the head with my “loserdom” relentlessly, while thinking to myself “really, am I such a poor catch?”

I just want to raise my kids now and think about what kind of legacy I can leave.

Dating feels like this competition that you have to win, and the guys I end up competing with, I frankly already lost to. I don’t have the energy (or at least, want to have the energy) to be a founder and CEO, or to run for political office. I want to tend my own garden and just appreciate the buds and the bees and watch the seasons turn and reflect on life.

Maybe there’s some woman who will ultimately just come and sit beside me as I do it, and not ever actually leave, and that’s fine. But I’m not going out looking.

And if she starts to compare me to other men or tell me I could and should have been so much more, I’m throwing her out earlier, not later. I’ve already earned my terminal degree, been married, had my kids, written my books, traveled internationally. My bucket list is done. Ain’t nobody going to convince me this time around to try to get back into that game.

It’s so much extra, hard work, and now that I have my kids, there’s no reward it can offer that I actually think is worth the investment.