Swipe Right, I’ve Got Wrinkles: A Midlife Dating Survival Story

Let me just start by saying: dating after 50 is not for the emotionally fragile, the technologically illiterate, or the romantically naïve. It’s a battlefield out there, and I entered it armed with a half-decent selfie, a glass of cabernet, and a healthy dose of skepticism.

I didn’t exactly choose to rejoin the dating world—I was sort of shoved back in, thanks to life, divorce, and the realization that watching cooking shows alone wasn’t the pinnacle of romance I once imagined it could be. But hey, I figured I’d give it a go. I mean, how bad could it be?

The answer: worse than you think and funnier than you expect.

First up: dating apps. Or, as I now call them, digital zoos filled with men named Steve who describe themselves as “easy-going but intense” (translation: emotionally unavailable and still angry at their ex-wife). I quickly learned that men on dating apps fall into one of three categories:

The “I took this photo in 2008 and I still think I look like this” guy.

The “Hi beautiful, can I tell you about my crypto business?” guy.

The “I’m holding a fish in every picture and I don’t know why” guy.

One man messaged me to say, “You look like the kind of woman who cooks with butter.” I still don’t know if it was a compliment or a cholesterol warning.

And don’t even get me started on profile bios. If I had a dollar for every time a man wrote, “No drama, just good vibes,” I could retire and date from my yacht. (Spoiler: they are always the drama.)

Still, I pressed on. I showed up to dates. I wore lipstick. I smiled. I listened to stories about vintage cars I didn’t care about and pretended not to notice when he ordered for me like it was 1952. I once had a man ask if I wanted to “go somewhere quiet” before our entrees even arrived. I told him I was somewhere quiet. Then I excused myself to use the restroom and never came back. (Sorry, Carl.)

But here’s the thing—they don’t warn you about the confidence glow-up that comes after 50. I no longer sit across from a man wondering if he likes me. I sit there thinking, Do I like him? Does he bring joy, or is he just tall and breathing?

When I was younger, I’d overlook red flags. Now? I wave at them as I walk out the door.

Oh, you think it’s “cool” to be vague about your life plans, live with your mom, and text me once every 8 days like that’s normal?

No, Greg. That’s a cry for help, not a dating strategy.

Don’t get me wrong—there have been some genuinely lovely guys. Some that made me laugh. Some that surprised me. And yes, one that told me I looked “pretty good for your age” and is now blocked on all platforms including LinkedIn.

But through it all, I’ve learned one golden truth: dating after 50 isn’t about finding someone to complete you—it’s about finding someone who doesn’t drain the fabulousness you’ve already built. If I’m going to let a man into my life, he better bring more to the table than heartburn and emotional baggage. At the very least, he should know how to make a decent margarita.

So yes, I’m swiping. I’m dating. I’m laughing. And I’m absolutely not lowering my standards just because someone’s still rocking bootcut jeans and calling it a “vibe.”

This is midlife dating, baby. It’s messy, ridiculous, and sometimes weirdly wonderful. And it deserves a playbook written with lipstick and sarcasm.

Wine, Wisdom & WTF Moments: A Midlife Dating Survival Story

Because dating after 50 still involves butterflies, weirdos, and the occasional emergency exit plan.

Let’s talk about the stuff people really want to know when it comes to dating after 50. Like...

SEX.

Yep. That little three-letter word that apparently terrifies some men in this age bracket almost as much as emotional intimacy or updating their profile picture to this decade.

Here’s the truth: Yes, sex after 50 is a thing. A very real, very wonderful, very underestimated thing.

But here’s the twist: you get to decide what it looks like.

Maybe you’re all about it.

Maybe you’re cautious.

Maybe your libido is living its best life while your knees are plotting your demise.

Whatever the situation—it’s your body, your rules, and your rhythm.

What it’s not is a favor you’re doing for someone just because he called you “babe” twice and split the bill at Olive Garden.

I’ve had men practically schedule a sleepover before I even got my salad. I’ve also had men who were so scared to kiss me goodnight, they looked like they were defusing a bomb. There’s no right speed—just your speed.

Also, if any man refers to it as “making whoopee”... please just leave.

Now, let’s talk about REJECTION.

Oh yes, rejection still exists in your fifties—but it hits different.

In your 20s, you cry into a pint of ice cream and overanalyze every emoji.

In your 50s, you delete the number, sip your wine, and say:

“Meh. Not my person. His loss. Next.”

I got ghosted by a man named Barry once. And honestly, I can’t even be mad—I’ve been ghosted by my Amazon packages before. At this point, I just assume if a man stops responding, he either got abducted by aliens or joined a monastery.

Rejection is just redirection. And redirection, darling, is your best friend.

But here’s the real plot twist: I’m not dating for him. I’m dating for me.

At this age, I’m not looking for a knight in shining armor. I’ve already rescued myself, thank you very much. I’m looking for a man who adds joy, not drama. A man who understands that I have a life, and he’s invited to join—not take over.

I like my freedom. I like my schedule. I like that I can cancel plans to take a nap and no one cries about it.

If I’m bringing a man into this calm, peaceful, wine-sipping existence, he better be someone who texts back, knows how to use punctuation, and doesn’t refer to women as “females.”

Dating for fun? Absolutely.

I’ve dated just for the hell of it. For the conversation. For the cocktails. For the experience of someone opening my car door and telling me my laugh is cute.

I’ve flirted shamelessly, laughed at cheesy pickup lines, and once told a man I was in witness protection just to get out of a weird date.

The beauty of midlife dating is that you finally, fully, gloriously know who you are. You’ve lived. You’ve lost. You’ve loved. And now, you get to choose.

Not because you need someone.

Not because time is running out.

But because you damn well want to.

So here I am. Swiping. Laughing. Dating. And sometimes deleting entire apps after one “Hey sexy, you up?” text too many.

But always—always—remembering this:

- You are not too old.

- You are not hard to love.

And you are definitely not here to babysit some emotionally stunted man-child with commitment issues and a flip phone.

Dating after 50? It’s ridiculous. It’s beautiful. It’s better than I expected.

And above all—it’s mine to enjoy.

Now pass the wine, and swipe responsibly.

- Been there, laughed at that? Drop your best dating-after-50 story below. Let’s turn our wild rides into wisdom… and wine-worthy tales.