The Older I Get, the More I Realize What a Loser I Am…and the Less I Care

There’s not a single standard I can meet anymore — thank god

It was only four years ago that I sat here on my couch with my best friend, Sunny, and we talked until late into the night about our romantic aspirations. We were both scared — neither of us had experienced a relationship in which we hadn’t been abused or betrayed. Yet there we were, two middle-aged women filled with hope, stars in our eyes, giggling like schoolgirls over the thought of falling in love again.

We had vastly different approaches. I couldn’t date anyone if I didn’t already have a crush on them. I couldn’t explore something romantic unless the feelings were there. Sunny was more practical. She was willing to start from scratch, using dating apps to meet men and see if sparks developed.

I was surprised to find myself the first one to dive into a relationship. He said he was going to take me to New York and Paris. He told me so many stories of all the adventures we would have.

But he ended things abruptly after our first weekend together.

Sunny was four or five guys in by then. She couldn’t help but give me a subtle, “I told you so.” She had not trusted my long-distance love. She already had a much better track record with getting out before permanent damage was done.

I thought I should take a break from my dating quest to find my footing again, but, while still shell-shocked, another suitor, someone I thought was a friend, moved in quickly, lovebombing me so relentlessly that I remained shell-shocked. Which, I suspect, is just how he wanted me.

There were no dreams of travel with this one — instead, he promised to take me to a realm I had never visited before: marriage and motherhood. He promised me forever.

Sunny said I was being a fool. Sunny was right.

I lied to her about how it ended. I was too humiliated to admit that every single word out of his mouth had been deception — and that I’d believed it all.

Today, as I sit here on this couch where we shared our romantic dreams together, we are no longer friends. She met a nice man last year. Over the course of their early courtship, she began to fade away from our friendship until one day, she was just gone. They are currently traveling the world together, and, I suspect, about to announce an engagement. He gave her everything my two men promised me: the world and forever. Only this guy meant it.

I never recovered from what happened to me. I don’t want to date, anymore. The thought of being alone in a bedroom with a man makes me physically ill. I don’t even remember what it felt like to have romantic dreams for my future. And I don’t miss it.

But Sunny did it. She wasn’t gullible and naive like I am. She held her ground, sorted truths from lies, and made her dreams come true.

I guess I’m what you might call a loser. And for the first time, I don’t really care.

I woke up a few days ago to photos of a couple who looked vaguely familiar to me — the man in the cowboy hat, in particular. They were all over social media. Who was this guy with the giant arms with a woman who could’ve been 20 or 50, hanging off his neck?

When I read the caption and saw it was Jeff Bezos, I nearly fell off my chair. Where the hell did he get those arms? And the cowboy hat? And the fiancée of indeterminate age? What is going on here?

I read the Vogue article that featured this image and found myself further stunned as I scrolled through paragraph after paragraph of socialite fluff. It was filled with labels and name brands of all the clothes the two of them were wearing during the interviews, and how fancy the house is, and how fancy (and big — the biggest!) the yacht is, and how cool the helicopter is, and how big her breasts are. (Yes, seriously.) And no, they don’t feel there’s any issue with their huge carbon footprint because they are doing so much work for the environment and humanity. It all really cancels itself out, in the end, doesn’t it?

I couldn’t stop thinking about this article. It’s in Vogue, for heaven’s sake. No, not hard-hitting journalism, but a major publication. And it occurred to me that we’re supposed to care about this. We’re supposed to be scrambling to consume a Jeff Bezos rebrand, embracing him as an American pioneer, a hero of the western world. And a hot motherfucker, at that.

We’re supposed to see them as ordinary working people while also being dazzled by their closets filled with designer clothing where a cheap t-shirt wouldn’t cost less than $600.

I was struck by the contrast between me and the members of this power couple. I spend my weekends in baggy jeans and ugly t-shirts from Walmart, hiking through the woods, sweat dripping down my face, panting and stumbling. You’ve never seen anything so unattractive in your life. Annie Leibovitz would pull a hard pass on taking my photograph.

I am a failure at everything this Vogue article tells me to aspire toward.

And I’m okay with that.

For the last ten years, I’ve watched successful businesswomen in their twenties and early thirties prance through fields in gingham dresses on social media, sharing their business expertise, and advertising their classes or coaching programs.

I’ve always been struck by these women. Seriously, they are beautiful. I mean stunning. If you look up words like siren, seductress, fox, goddess, and knockout, you would find images of these women. The long, curly hair. The flowing skirts and ankle boots. Smooth legs and full, pink lips.

But that’s not all: they’re all in the Six-Figure Society. That’s right, their businesses are so successful, they regularly bring in at least $10,000 a month. And they did so in less than three years of starting those businesses.

They live with their husbands in tricked out cabins in the woods or elegant New York City apartments, far from those Instagram fields in which they frolic. And they’re friends with all the other gingham-clad, bare-footed business goddesses who show up on my social media feeds.

I’ve spent the last decade trying to be like them. You’ve seen it — me in my red dresses, frolicking in the forest.

But all this time later, I’ve never joined the Six-Figure Society. I’ve never even gotten close. It takes me at least five months to earn $10,000.

And let’s face it: What am I even doing out there in the woods in my dresses with my hairy armpits, chubby tummy, and lined skin? I look ridiculous. I’m not pretty and never have been. I’m not feminine and never have been. I look like a clumsy elephant trying to pretend she’s a swan.

But that’s okay. I like who I am just enough not to care. Sure, I wish I was beautiful and feminine. Sure, I wish that beauty and femininity translated into social media followers which then converted into customers. Sure, I wish I made $10,000 a month. (Hell, I wish I made half that.)

Yet I feel incredibly grateful to have the life I have. I may barely bring in enough money to pay the bills most months, but I am free.

I am my own boss. I write what I want to write. I make my own deadlines. And if I want to eat lunch by a river on a Wednesday, then goddammit, I do.

So I guess I’m kinda a loser when it comes to my career. I’m almost 50 years old and women half my age are making it rain.

Yet in some ways, I feel like one of the wealthiest people I know.

When I’m hiking, everyone passes me. Women in their sixties with knee braces on. Kids under the age of 5. No matter how hard I push myself, how in shape I am, I am always the one who is in everyone’s way.

I still buy CDs because I can’t figure out how to get my auxiliary cable to work in my car. I spend hours making elaborate recipes but my healthier substitute ingredients generally ruin the chemistry of the dish and everything — including the time I took to make it — ends up in the trash.

I wear socks with holes in them. I don’t shave my legs. I have mild hearing loss that makes phone conversations a little awkward. I can’t see anything without my bifocals.

And I never got married or had children.

I don’t know anyone who is more of a loser than I am.

But I’m okay with that.

© Y.L. Wolfe 2023

Y.L. Wolfe is a gender-curious, solosexual, perimenopausal, childless crone-in-training, exploring these experiences through writing, photography, and art. You can find more of her work at yaelwolfe.com. If you love her writing, leave her a tip over at Ko-fi.

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