Dating is Like Shopping at Goodwill

Finding love at midlife feels less like Cartier and more like digging through Goodwill sales bins

It started on an ordinary Tuesday night in the kitchen. I was standing at the stove, making homemade spaghetti sauce, when my daughter hopped onto the counter like she always does when she wants to talk. There’s something about that perch close enough to be in the middle of things, far enough to be an objective observer. The subject of dating comes up a few times a year. Specifically, my dating life at middle age and how challenging it is at this stage of life. She tilted her head, about to pop another kale chip in her mouth, when she said, “It’s like shopping at Goodwill.”

“What?”

And then she began, ticking things off on her fingers like she was giving a presentation.

“Everything’s used. Some cracked. Some broken. Missing pieces. A slight odor you can’t quite place. And definitely stains.”

I laughed hard because honestly she wasn’t wrong.

The list was so brutally accurate that it could be its own TED Talk. And before I could add my own commentary, she broke into song. Half serious, half joking, singing, “You can’t always get what you want…”

The most perfect soundtrack and absolutely hilarious in the moment because she was right. Last time I dated, I was a teenager. Shiny and new, in the best shape of my life, full of optimism and hope, with the world laid out before me. On a college campus, where potential partners were plentiful. Everyone is at the same starting point in life, trying to figure out who they are, what they want, and looking for someone they like along the way. The dating pool was diverse, with all shapes, sizes, cultures, and races. It was fun and exciting. But in middle age, life doesn’t always go as planned. We don’t always end up where we want or with whom we want. Careers detour, marriages collapse, dreams shift, losses accumulate. The best-laid plans of mice and men often go awry.

Maybe the comparison to Goodwill wasn’t so far off after all.

The Store We Didn’t Plan to Shop At

Dating in your twenties and thirties is like walking into Nordstrom or Neiman Marcus. Shiny mannequins dressed in coordinated outfits. Soft music plays in the background. The smell of new leather and clean perfume hangs in the air. The merchandise is arranged by size, by color, and fully in stock. You walk in with an idea of what you’re looking for, and more often than not, you find it. Everything is fresh, clean, and new. No makeup stains, rips, or tears. Just perfectly pressed pleats and starched collars.

But dating in your forties, fifties, and up? That’s not Nordstrom anymore, babe. That’s Goodwill on half-price Wednesdays.

The racks are overstuffed, hangers tangled together in ways that make no sense. Sequins dresses smashed beside men’s sweatpants, obviously rejected and put back in the wrong place by the previous shopper. A single shoe sits abandoned in the corner, its mate lost somewhere in the store. Somewhere, a toddler is crying, someone else is bargaining with a cashier over whether the chipped mug should really be $1.99. The lighting is fluorescent, a bulb or two buzzes with too much current, and another flickers until it finally burns out. The air is a weird combination of others’ household scents, mixing together in sometimes the worst ways.

And there you are, sifting through each item, the mismatched hangers squeal against the scraped-up rod that’s seen much better days about two decades ago. Trying to find something that’s still in style, doesn’t have noticeable stains, and hasn’t shrunk two sizes from the original tag. Hoping against the odds, you might stumble across that hidden gem tucked between the polyester blazers and the ill-fated denim skirts unnoticed by so many others before you.

We All Become Pre-Loved Eventually

By midlife, no one is fresh off the rack anymore. We’ve all been worn, stretched, snagged, and softened by the lives we’ve lived. Marriages and divorces, career highs and collapses, health scares, kids, heartbreaks, and betrayals. Every one of those chapters leaves its mark, like faded fabrics and scuffed shoes.

When we were younger, we wanted brand new. The latest fashions. Tags dangling from the side seam with crisp fabric untouched by others and time. But at this stage in life? We’re all “pre-loved.” And there’s an odd kind of comfort in that. Knowing every garment on the rack has its own story stitched into the lining.

Still, it can feel daunting. Because you never quite know if what you’re holding is a diamond in the rough or something that belongs back on the return cart. That leather jacket? Gorgeous until you spot the rip along the shoulder. That cashmere sweater? Luxurious except for the wine stain spreading like a shadow across the hem. That dinner date? Polished and charming until he casually mentions he hasn’t spoken to his kids in five years. Handsome and attentive until five beers in an hour, he admits he’s fallen off the wagon again. Funny and magnetic until you realize every story he tells circles back to how “crazy” all his exes are. They are the problem.

And so you stand there, hanger in hand, asking yourself the same question again and again: Do I patch this up and make it work, or keep rummaging through the bins holding out hope for a better find?

You Can’t Always Get What You Want

And that’s where the song loops back in. My daughter, half-teasing, half-true, sang it in the kitchen that night, “You can’t always get what you want.” Mick Jagger might not have been thinking about middle-aged dating when he wrote it, but he could’ve been. Because what we thought we wanted back then isn’t always what we actually need now.

At twenty, we wanted fun, carefree, and flawless. Everything fresh off the rack. Crisp white shirts without a wrinkle. Bright smiles that hadn’t weathered disappointment. Hair so shiny it caught the light when you walked into a room. The résumés were still short but polished, featuring internships and promising career prospects. Lives smelling of new-car leather. Clean, untouched, and all momentum, nothing but forward.

But at this stage? The wish list changes. What I need looks different. I don’t need untouched. I need durable, having weathered storms and battled scars, strong and fortified by them. I don’t need perfect and untested. I need proven, time-tested, and loyal. Someone who knows how to sit in a disaster without panicking and formulate a plan forward. Someone who won’t run at the first sign of problems ahead or life going awry. Someone who has faced loss and heartbreak and rebuilt themselves brick by brick.

Proof that getting what you need might be the better way. The cracked, the chipped, the faded isn’t the deterrent anymore. It’s proof. Proof of survival. Proof of resilience. Proof that life tested them, and they’re still standing. Like that leather jacket that feels better once it’s broken in. Or the vintage boots softened by years of walking. What lasts isn’t what’s flawless, but what’s endured.

And maybe that’s the quiet wisdom tucked into the chorus my daughter sang, laughing at the absurdity of it all. We don’t always get the spotless version we want. The “perfect” partner, the shiny new start of life, where everything and everyone is still possible. The untouched story. But if we dig a little deeper into the bins and stay more open-minded about our choices, we never know what we’re going to find.

Closing the Store

Goodwill teaches you to look differently. To shift your expectations. To notice the worth in what others might have discarded. The broken zipper? That can be fixed. The missing button? Easy to go to the fabric store, buy another one, and sew it back on. The faded T-shirt? It might be the softest thing you’ll ever wear.

Dating at middle age asks the same of us. To stop chasing flawless packaging and start seeing the depth, the resilience, the hard-won wisdom stitched into people who’ve lived enough life to know what really matters.

And yes, it can feel daunting. Dating now is messy, unpredictable, and sometimes disappointing. There are days when the racks look barren, the options bleak, and you wonder if maybe it’d be easier to stop shopping altogether.

But every so often, you stumble on something remarkable. A designer piece tucked between winter coats. A treasure you didn’t even know you were searching for until it was right there in your hands.

And isn’t that precisely what the song says? You can’t always get what you want. You can’t count on flawless. You can’t demand perfection. But if you keep showing up, laughing at the hunt, and staying open to possibility, you might get what you need.