Swipe, Ghost, Repeat: The Brutal Truth About Dating

Let’s get one thing straight: I just found out that dating after 50 is not for the faint of heart. It requires a kind of resilience you didn’t even know you had. It’s a world where you swipe left on a shirtless man flexing in his dingy bathroom mirror, only to have him pop back up like an un-flushable toilet. Where promising conversations vanish into the void, and where “age is just a number” is often the battle cry of 60-year-old men openly stating that they are seeking women 18 and up.

What? Really? Dude!?

Once upon a time, romance unfolded organically—college sweethearts, office crushes, friends of friends who turned into lovers. You met people in real life, in spaces where, for the most part, meaningful interaction came before you  started thinking, What would it be like to actually kiss this guy?

But here we are, navigating the digital bazaar of human connection, armed with life experience, a good sense of humor, and (ideally) a solid WiFi signal.

Now, you’re expected to assess romantic potential based on a handful of photos and a bio that’s either criminally vague—“I love adventure” (how does one even read that?)—or alarmingly specific—“The way to win me over: back scratches and seltzer or home cooked meal (true story, by the way).

And so, you take the plunge. Maybe it’s curiosity. Maybe it’s the reality of working from home and no longer frequenting bars or attending many social events. Maybe your best friend insisted. Maybe you’re just tired of watching everyone else being coupled. Or maybe you want to prove to yourself that, against all odds, there are still great men out there and “your person” is just one swipe away.

Whatever the reason, here you are, navigating the algorithm-driven circus that is modern romance.

The Profile Paradox

First, the challenge of crafting your own profile. Do you present yourself as the well-rounded, sophisticated woman you are? Or do you lean into the cliches, pretending to enjoy surfing, even though the last time you tried, you lost an expensive pair of sunglasses and nearly drowned and swallowed a mouthful of saltwater?

Crafting a profile should be simple in theory: Successful in business, active in life, and most certainly not looking for a sugar daddy. (I have my own money, thank you very much.)

Meanwhile, men (bless them) seem to have received a universal memo that dictates their photo choices:

• Holding a big fish (Is this meant to showcase survival skills? A backup plan for economic collapse?)
• Posing with a dog or a cat (To prove sensitivity, I guess?)
• Standing next to a sports car (that may or may not belong to them)
• Lifting very large, heavy weights (Virility? Competence? A cry for help?)

And then, of course, there are their bios.

Some, aggressively uninspired:

• “Fluent in sarcasm.” (Translation: “Incapable of sincerity.”)
• “I’m looking for an honest woman.” (As opposed to what? A pathological liar?)
• “No drama, please.” (Meaning…he has been the main character in multiple dramatic exits.)
• “Looking for my best friend.” (Possibly seeking an unpaid housekeeper.)
• “Favorite Sundays: Watching football and drinking beer.” (Well, at least you’re self-aware, but just grab a couple of buddies and go at it.)

Others are so wildly ambitious, you wonder if they’re written in earnest: “Looking for someone fit, fun, and flirty, who can travel at a moment’s notice, loves the outdoors, speaks a few languages, works out five times a week, and has no baggage.”

Sir, if she exists, she is dating someone half your age and has never even considered this app.

And then there are those who are reading philosophy books and authors I have never heard of—and am too uninterested to google.

The Swipe Circuit

Once your profile is set, the real work begins. Swiping becomes a daily ritual—equal parts thrilling and demoralizing. Occasionally, you come across someone promising. Someone seemingly intelligent. Someone who, most importantly, knows how to express himself with complete sentences and spellcheck.

But then, reality strikes.

Maybe they never respond to your opening message. (What do you even say without being too overt? “Hi”?)

Maybe they chat for three days, then vanish like a Victorian child into the mist.

Maybe they ask you to meet them in another city. (Why? What’s wrong with New York?)

Maybe they just want to chat…endlessly. Let’s “get to know each other,” which sounds nice, until you realize it means living forever in the talking phase.

Or they want to meet immediately. (Sir, let me at least remember your name first.)

Or they claim to be 5’7”, which you think is a little shorter than you’d like, but, hey, they seem so nice, until you meet and realize your eye-level with his forehead.

What’s the right move? Do you ghost them? Do you send a polite rejection? How do you even say, “Hey, you’re just coming across as a weird, lonely person, and our conversation makes me feel like I’m chatting with an AI chatbot that’s malfunctioning?”

I don’t often agree with Trump (read: never, on just about anything), but when he joked about a 300-pound guy sitting alone in a basement catfishing people, I felt that.

The First Date Gauntlet

So, let’s say you actually make it to an in-person date. You put in the effort, find an outfit that sends the right message, and arrive at the place he suggested, which, let’s be honest, tells you a lot about him.

The setting is almost always a coffee shop or wine bar: neutral, low-investment spaces where escape is quick and easy, if needed.

Within the first five minutes, you already know.

He leans in and calls you darling a little too soon.

He mentions his late wife in every other sentence.

He talks about his pharmaceutical sales job as if he’s single-handedly saving humanity. (Too unnerving for a lifelong wellness aficionado.)

He subtly evaluates you like a showroom car, hand grazing your back, as if checking for firmness. (Sir, this is a date, not a pre-purchase inspection.)

He lets me pay for my tea and his coffee. (Wow!)

And then, of course, there are the younger men. The fresh-faced 30-somethings who slide into your messages with disarming confidence, declaring that “older women are less drama” (translation: likely more desperate to take things to the next level, quick).

Oh, to be valued for my emotional stability and expertly curated style. 

Do they think we all come with an identical instruction manual?

Ah yes, the universe can be funny. And at times, almost cruel.

The Unexpected Joys

And yet, for all its absurdities, online dating after 50 isn’t without its surprises.

There are those rare moments when a match turns into a real connection. When someone’s quirks align perfectly with your own. When you find yourself genuinely excited for the next message, the next date, the next possibility.

Okay, that hasn’t happened to me…yet, but I’ve heard it’s possible and have read about it in New York Times Sunday wedding section. A friend of mine found her perfect match after enduring 80 dates. (No joke.)

And then, there’s the camaraderie among digital warriors. They trade unsettling stories like battle-scarred veterans: the man who forgot to bring his wallet to dinner, the woman who refused to order appetizers until she checked his horoscope, and so on.

And perhaps, most importantly, there’s adventure. The thrill of stepping into the unknown, of rediscovering parts of yourself buried beneath decades of routine relationships or marriages. You may not find the love of your life on these apps, but you will find stories. Laughter. And, if nothing else, a newfound appreciation for the stability of singlehood.

Because, at the end of the day, whether romance finds you or not, one thing remains certain: The ability to laugh at it all might just be the best survival strategy of all.

(BTW: All the stories are true!)

Cover image generated by Drew Green with Midjourney