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Dipping your toes in the dating pool in your 50s and beyond? Yeah, me too. In fact, I’ve been at it for almost a decade, so I have some things to share with you. I’m sure there are books to read about this subject, but you know what’s even more helpful (I think) is getting CliffsNotes from someone who’s been going through it.
When I divorced, I honestly thought there would be no fewer than one hundred variations of men who looked like Brad Pitt, were emotionally developed, charming and grateful to meet a woman who knew what she wanted.
I’m still looking.
What I’ve found instead are a lot of men who feel inadequate, struggle with communication and have emotional wounds that rival my own. This is not a male-bashing article — it’s an honest, informative piece about what dating in your 50s really looks like and how you can navigate it with compassion and confidence.
1. Everyone at this age has emotional baggage.
Every man I’ve met has been in a long-term relationship that has affected him. At this point in life, we all have scars, and the first step is to have empathy for yourself and your experiences so you can have empathy for a potential partner.
Of course, we’d all love to meet a man who’s dealt with his divorce in a healthy way, has no bad feelings toward his ex and handles life’s struggles without drama. But that man just doesn't exist.
Divorce is hard and can have a long grieving process. It’s expensive. It can completely change your lifestyle, and that can break many people down, especially men. Remember that when you meet a man, you are both showing up with a past. The key is to learn whether someone can recognize the difference between a person who is working through their “stuff” and someone who is stuck in it — and be honest about where you fall in that spectrum, too.
2. No matter how “together” you are, you’ll get ghosted. And yes, it still hurts.
It doesn’t matter how confident, accomplished or emotionally mature you are — ghosting still happens. Whether it’s someone from a dating app you’ve never met in person and you’re still in the talking stage, or someone a friend set you up with and you’ve had a few dates, unfortunately, grown men and women are treating each other this way. It’s happened to me, and I’m guilty of doing it too.
However, I soon realized how terrible it felt to go quiet on someone because of my personal s**t, so I stopped.
Yes, it can be incredibly hard to tell someone you’re dating or just messaging that you’re not interested for whatever reason, but it’s a lot kinder than ignoring someone.
Realize that if someone disappears, it likely has nothing to do with you, and you’ve put yourself out there — which is a huge accomplishment after divorce.
And if you ever get the urge to stop talking to someone because you’ve met someone else or decided you’re not ready to date, I’m telling you it feels better to let them know. My go-to is to say I just don’t think we’re a match. It’s clear and not personal.
3. Your standards will be higher. Keep them there.
In your 50s, you’re more aligned. You know what you don’t want, and that’s a gift. Your tolerance for people who can’t meet you where you’re at isn’t very high, so it will take longer to meet someone you’re compatible with. That can be the tough part, and you may have lonely days and wonder where the hell he is.
But stay open. Rather than looking for a flawless résumé or the perfect body, women in their 50s value emotional maturity, kindness, character, consistency, actions that match words and shared values. That’s what’s attractive, and while it's hard to find, there are people out there with all those qualities. They might not look like your usual type or check all your boxes, and that’s okay.
So remember, when you’re feeling frustrated and meeting men who just aren’t doing it for you, it only takes one person whose life fits nicely with yours and who can make your journey a little sweeter.
Dating in your 50s isn’t for the faint of heart — but it’s also not without its magic. This is your reminder that you’re wiser, you know yourself better and you can show up with experience. It’s okay to be vulnerable, but don’t let that stop you from being open, because there’s a good chance you’ll find a connection that feels like coming home.
Are any of you dating right now? How's it going? Let us know in the comments below.
Jess Jenkins
