Online Dating in My 40s 👫 Why I’m Completely Done 💔

September 26, 2025 by FlipFlop The Clown in Discussions

Online dating is supposed to make meeting people easier, right? Swipe, match, chat, meet. Sounds simple. But in your 40s—especially as a single guy who’s just trying to be upfront and honest—it feels like running headfirst into a wall, over and over again.

Physically, I’m a good-looking guy. I diet and exercise every day, stay active, and hit the gym regularly. I don’t have any problem attracting attention from women, and I’m confident in my appearance and who I am as a person.

I’m a Cuban American, raised in Miami, now living in Orlando. I’m 43, single, no kids (by choice), and never been married. I’ve got my own place, I live alone, I pay my own bills, and I make it work—even if that means living paycheck to paycheck and driving a moped instead of a car.

It’s not like I’m sitting around doing nothing, either. I’ve been grinding—sending out résumés daily, applying to hundreds of jobs. The economy and job market are brutal right now. But at least I’m out here trying. At least I’m putting in the effort. You’d think that would count for something. Apparently, it doesn’t.

I’m not rich, but I’m responsible. I’m a funny guy, a kinky guy, a creative person. I’m honest, loyal, and I’ve got a huge heart. When I fall in love with someone, I give them everything and more. That’s who I am.

The Harsh Reality

What I’ve noticed about dating in my 40s is that most of the people who are single and in my age group—at least here in Orlando—don’t want a serious relationship. They just want to fuck around and keep things casual.

Meanwhile, I don’t want to waste my time. I want to settle down, get married, and have a family. But here’s the reality: most singles I meet in my age group either have kids, are still married but “separated,” or are carrying so much baggage that a real relationship feels impossible.

Some expect me to be the father of their kids while their baby daddy is still in the picture. Others don’t even make their ex pay child support, yet they expect me to step in and take on that responsibility. Some are still legally married, “separated,” and trying to date while dragging me into the middle of their unfinished mess. Others are going through a divorce and trying to sell their house while their ex-husband is still lingering around causing chaos. And they expect me to wait around a year or more until their divorce finalizes.

I’m not signing up to be a stand-in dad, a rebound, or a distraction while you figure your life out.

Baggage & Drama Everywhere

Everyone’s got baggage, sure—but what I’ve run into feels like straight-up chaos. Married but separated. Divorce drama. Exes lingering around. Baby daddy issues that never seem to end.

What I’m looking for is pretty simple:

Is that really too much to ask?

When Ego Turns Into Hypocrisy

Then there’s the ego. The “I deserve a man who makes six figures” crowd. Meanwhile, some of these same women are broke, living with roommates, or struggling more than I am. But I’m “not good enough”? The hypocrisy is mind-blowing.

And don’t get me started on the women who brag about traveling the world. You know the type — the ones with ✈️ in their bio like it’s a badge of honor. They’ll post nonstop about their latest “soul-searching journey” in Italy or “spiritual awakening” in Bali, but suggest meeting up an hour away and suddenly it’s “too far.” You’ll hop on a plane and cross an ocean, but won’t cross the highway? Make it make sense.

Money, Money, Money

Some women brag about their income and assets, others judge you based on your paycheck. Like, congrats on owning a house or making six figures. That’s great for you. But unless you’re planning to share that with me, why should I care?

Whatever happened to connecting because you actually like each other? Here in Orlando, that feels like a dying art.

The Foot Fetish Factor

And yes, I’m upfront about my foot fetish — I’ve never hidden it. It’s literally the first line of my bio:

BORN WITH A FOOT 🦶 FETISH!
(Swipe left if that’s a dealbreaker.)

Yet some people don’t read. They match, start chatting, and the moment I mention it, half ghost, and some try to shame me for it. The few who stick around? It usually still doesn’t work out.

I figured being honest would earn respect. Instead, it often earns silence or judgment. And that’s fine. I’d rather be rejected for being real than liked for being fake.

The Free Meal Problem

Three years of trying. Countless conversations. Exactly two women I’ve actually taken out on real, physical dates.

And it’s not because I don’t talk to people—I’ve spent hours on the phone with women I’ve met through these apps. But what I’ve noticed is a lot of them just want a free meal. They’re more interested in the expensive restaurant I’ll take them to than in actually getting to know me. That’s why I haven’t gone on many dates—I refuse to waste my time and money on people who see me as a dinner ticket.

Time Wasters & Dishonesty

A lot of women on these apps are time wasters. They’ll talk to you nonstop day one, hit it off with you, and then day two they ghost, block, or start replying with shady one-liners like they’ve lost all interest. Some block me for no reason at all, and I never even know what went wrong.

And then there’s the dishonesty. Some leave out major things on their profile—like not mentioning they have kids, or not mentioning they’re still married. I’ll only find out hours into talking with them. That’s not fair. That’s wasting my time.

It’s not just online dating, either. I’ve gone to singles social gatherings and even tried speed dating, hoping to meet someone genuine in person. Same story—people wasting time, people not serious, people showing up with walls of baggage or just looking for entertainment.

And honestly, a lot of these events feel like cash grabs. The hosts will charge an upfront cover just to meet in a public place that’s usually free to enter, give you a list of icebreaker questions, and then disappear once they’ve pocketed the money. No real effort goes into helping people connect—it’s just another way to take advantage of people who are genuinely trying to meet someone.

A Heartbreaking Experience

The last woman I was talking to really hit it off with me on day one. We met on one of the dating apps, exchanged phone numbers, and started talking. She even told me she wanted to have kids with me. She already had a child, and her baby daddy wasn’t in the picture.

We were talking about the future—getting married, starting a family together—and this was only a few hours into our connection on the app, including phone calls and FaceTime. She even wanted to come over to my apartment that same day. Things felt amazing.

I’ll be honest, most single guys in my age group aren’t looking for single moms. I wasn’t really looking for that either, but we hit it off so well that I decided to overlook that and give her a chance.

Then, day two, she found out I live paycheck to paycheck and drive a moped. Suddenly, her energy changed. She no longer wanted to talk about a relationship, marriage, or a future together. The next thing out of her mouth was “friends with benefits” and that I could be her “sex slave” instead.

I was heartbroken. All the trust and potential we had vanished as soon as finances came up. Apparently, I wasn’t good enough to be her man—but I was good enough to fuck. Imagine if the tables were turned and a man said that to a woman—it would be seen as completely unacceptable.

Long story short, we never actually got to meet in person, and things didn’t work out.

I'm Done

Dating in your 40s isn’t dating—it feels like a job interview:

Meanwhile, I’m out here being upfront and honest about who I am and what I want. I’ve been loyal, funny, creative, and responsible, even if I’m not rich. I’ve worked hard to put myself out there, and I’ve tried. But after years of running into walls, I’m done.

I deleted my dating profiles. I’m not playing this game anymore. At this point, I’d rather be single and at peace than dating and drained.

If someone genuine comes along someday, great. But until then? I’m investing in myself.

Thanks for reading, and good luck to anyone else out there navigating this mess. Stay strong.