#Swipe Right or Walk Away. Dating Later In Life.
Life’s Funny…Until It’s Not™
Dating later in life is a whole different sport than it used to be.
Do you remember what it was like dating in your 20s or 30s? I do. Fun, exciting, lots of energy, definitely adventurous. Now? At age 55+? Where do you even begin? Do you even have the energy? Is it exciting, or does it feel like you’d rather stay home in a nice comfy pair of sweats?
When we were younger, all that time we spent picking out the right outfit, doing our hair and makeup, wax on, wax off… it was part of a time in our lives we looked forward to. Now, do we even have the energy to do half of what we used to? This time around, it might be a pair of Spanx, comfortable sexy shoes (is there such a thing?), and we’ve gone from the black sexy dress to black slacks and a smart-looking sweater. Even though men might not put in as much effort to look 20 years younger, they have their own rituals as well. It’s not easy on either side — this thing called dating in the modern age.
Where Do We Even Meet People Anymore?
Then there’s the question: where do you meet people in your own age range these days? When I was in my late teens and early twenties, we went out to places where we could dance, have a few drinks if you were of “drinking age” — wink wink. There was even one very cool place we’d go — and this was before cell phones — that had actual rotary dial phones at the booths. If you saw a cute guy at another table, you’d dial his table number and hope he’d pick up. If I remember correctly, it was called the Dial Tone Lounge. If it worked out, you’d end up on the dance floor, and who knows… I’ll let your imagination run with that one.
Now here we are — like me at 66 — wondering how we meet someone to go to a movie with, go antiquing, share a meal, explore parts of the state we didn’t even know existed. Just spending time with someone we might enjoy being around. We’re not hanging out in bars or out dancing on weekends like we used to, but we still want to spend time with someone.
Dating Apps: Taking the Plunge
Okay, hold on. I’m going to say those words you might not be ready for: dating apps.
Oh my goodness. What the heck have I done? The questions start running through your mind: Which apps are the legit ones for people 55+? How do I spot an imposter? What are the red flags? Good profiles versus bad profiles? And when do you take a chance and swipe right?
Oh wait — what the heck is swipe right? In the world of dating apps, swipe right means it might just be a possibility. Then that moment hits: What have I done? How do I unsubscribe from the dating world? Panic takes hold for a moment. Deep breath. You think about the worst that can happen — you just don’t make any dates. It’s okay. Really.
But if you decide to dip your toe into the dating pool, then good for you! Dating these days can be an exciting proposition or a terrifying thought. This time, while you’re dipping your toe, you know what you’ve liked and disliked from past relationships. Lean on those. Write them down, and don’t be afraid to share them with your potential new person. Know this as well: there’s less pressure dating this time around. If that first date doesn’t feel right, say thank you and swipe right again. Or maybe it’s just not the right time for you, and in that case, X out of dating… for now.
My Dating App Experience
Let me share one of my dating experiences (yes, I said one — there might be one or two others, but I’ll keep those for another time). One time, I swiped right and met a nice man who was soon to be a retired mailman. One of the first rules you need to learn is that the first date should always be in a public location, and you should always tell someone that you’re meeting someone for the first time — when and where. After we texted for a while and felt like we should take it to the next step — oh my — I met my guy at a McDonald’s for coffee.
The coffee date was nice, but he made one irritating comment. He told me that I was one of three he had met for coffee that day, and I was the winner. The winner? Anyhoo, I let that go, and we did date, even moved in together, but unfortunately, it didn’t work out in the end. Oh, did I mention that he drove his car like a mail truck? Stop-and-go, stop-and-go, like going from mailbox to mailbox. I mentioned that to him one day. Let’s just say that conversation wasn’t a winner. But you know what? It was okay. I am okay, and I was just fine on my own.
Because here’s the truth: Dating is an option, not a requirement. Keep that at the top of your list — because the most important relationship you have is still the one with yourself.
So if this is you — 55+ and looking to dip your toe in the dating game — go for it. Let someone know that you’re going to give it a go. Your safety always comes first. Make sure you have a checklist of what to look out for, good and bad. Always give someone a heads-up that you’re meeting someone for the first time and where you’ll be. Be smart, but also enjoy this time of your life. Have fun, do a little dance. You’ve earned it.
Food for Thought: Matlock and Ageism
It took me a minute, but I started watching the new Matlock series starring Kathy Bates. I now wish I had started sooner, because I didn’t realize how much it would reflect what has happened in my own life over the last couple of years. The show is about a woman in her 70s who goes back to work as a lawyer — essentially starting over as a rookie. That’s how it starts off. Definitely add it to your watch list. But what really gets me is the ageism she faces from the beginning of the series and throughout. In the first episode, the character Matty says that women of her age are invisible to society. People underestimate her, dismiss her, assume she’s past her prime. Sound familiar?
Here’s why this resonates so deeply with me: I retired in November of 2024 after experiencing ageism in the workplace. I’ve been working since I was 15. That’s over 50 years of having a job to go to, of knowing who I was in that 9-to-5 structure. So when I made the decision to take early retirement — I won’t be 67 until April 10th, 2026 — I had to ask myself: was this the right choice? Who am I without that job? Am I going to be okay not having that routine, that identity?
But here’s what I knew: my responsibilities as my parents’ caregiver were only going to grow. I had a lot on my plate. And honestly? The workplace that pushed me out because of my age didn’t deserve my energy anymore. So yes, I made the right decision.
Watching Matlock reminds me that retiring — or dating, or learning something new — isn’t about being done. It’s about choosing what comes next on your own terms. Kathy Bates’ character shows up, uses people’s assumptions against them, and proves she’s got more to offer than anyone expected.
And you know what? So do we. Whether it’s dating at 66, starting a podcast, or just figuring out this next chapter — we’re not done. We always have something on the back burner. We’re just getting started.
What I’m Learning: Finally Opening the Keyboard
So, remember that keyboard I bought? The one that sat in the box for… let’s just say longer than I’d like to admit? Well, I finally unpacked it. It took a few days to get it all together — it came with a stand and a stool — but it’s set up now, and I’ve actually started learning.
I found an online app that had good reviews, signed up for the pro version, and started following the lessons. And here’s the surprise: I’ve actually found it to be a better experience than I expected. There’s something satisfying about those first few lessons, about being a complete beginner and seeing even tiny progress.
Now, I’ve only gotten through the first week of lessons because life has thrown some curveballs lately — caregiving responsibilities have shifted in ways I didn’t expect. I won’t lie — it’s given me brain fog on many days. But you know what? I’m glad I made the purchase. That keyboard isn’t going anywhere, and I do want to get to a point one day where I actually play a song. Hope springs eternal, right?
And here’s the thing I keep reminding myself: learning something new is always important for cognitive brain health. Even if I’m only getting through a lesson here and there between everything else, I’m doing something for myself. I’m being a beginner again, just like we talked about with dating — willing to be awkward, willing to start from zero, willing to try.
So if you’ve been thinking about learning something new — an instrument, a language, a craft — this is your sign. Unpack that thing. Sign up for that class. You don’t have to be good at it right away. You just have to start.
Final Thoughts
One thing I’ve learned over these last several months is that life doesn’t always move at the pace we think it should. And honestly? That’s okay.
My caregiving responsibilities have shifted significantly. Some days I have all the energy in the world. Other days? Brain fog rolls in, and I can barely string two thoughts together. I’ve had to learn — and I’m still learning — to be okay with that rhythm. To not fight it. To not feel guilty about it.
And here’s what’s interesting: in slowing down, I’ve actually started noticing more. Like that keyboard, I finally unpacked. Or the fact that dating at 66 is completely different than dating at 26 — and maybe that’s actually better. Or watching Kathy Bates play a woman who refuses to be invisible, and realizing… yeah, me too.
This stage of life — 55, 60, 66, 70, wherever you are — it’s not the ending people make it out to be. It’s just… different. We’re not done. We’re just getting started on a chapter that actually might be the best one yet, because this time we know who we are. We know what we want. And we know what we’re not willing to settle for anymore.
So if you’re navigating something hard right now — caregiving, retirement, dating, learning something new, or just trying to figure out what comes next — I see you. You’re not alone in this. And you’re doing better than you think you are.
Remember: Life’s Funny…Until It’s Not™, or you’ve swiped right.
Listen to “Life’s Funny…Until It’s Not™” the first two Sundays of the month at 7 pm EST on the R2RB Network at www.r2rb.com
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