Dating after 50 isn’t for the faint of heart—or the faint of Wi-Fi signal. Between deciphering emojis, dodging gaslighters, and trying to remember how flirting works (does a wink still mean what it used to?), the modern dating scene can feel like a full-contact sport with fewer hormones and more joint pain.
I’ve been out of the dating scene for so long now I wouldn’t even know how to flirt or if someone was flirting with me. No clue. And while I wouldn’t mind finding a partner, dating seems exhausting and complicated.
But it’s not all doom, gloom, and dad jokes. Whether you’re newly single, divorced, or just finally ready to find someone who shares your love of travel and tolerates your snoring, dating over 50 can be both hilarious and hopeful.
Today, I want to share some unique challenges that women over 50 face when entering the dating scene.
15 unique challenges that come with dating after 50
Here are 15 weird and unique challenges that come with dating after 50. When I was still living in Canada and dating after I left my ex, I came across a few of these. After 2 dating two men, I threw in the towel and moved to Guatemala.
Now the dating scene here is almost non existent for women over 60 but I still have hope that I’ll meet someone one day, either chasing a street dog or singing Sia at the top of my lungs at the karaoke bar.
Who knows.
The Dating Pool is Smaller (and a Bit Shallow Sometimes)
Let’s be real—there just aren’t as many available people over 50 as there were in your 20s and 30s. A lot of folks our age are married, partnered up, or just not looking. And those who are available might not be emotionally available, if you catch my drift.
Watch out for and catch any red flag you see on the first date and if something feels off, it is! Trust your gut instincts.
He’s not the only fish in the ocean but he ain’t swimming with millions anymore either.
Online Dating Can Feel Like a Second Job
Dating apps are the go-to now, but navigating them after 50 can be exhausting and confusing. Swiping, ghosting, endless texting—it’s a digital battlefield and I’m not here for it.
Not all apps are designed with mature daters in mind, so it can feel like trying to find love in a noisy bar with the lights off. Hard pass.
If you’re up for the challenge, here are a few dating sites that might interest you.
Happy surfing!
Baggage is Pretty Much Guaranteed
By 50, most people have some kind of history—divorces, kids, heartbreak, exes who won’t go away. That’s not necessarily bad, but it means more layers to work through. Love isn’t just about chemistry anymore; it’s also about unpacking and understanding each other’s pasts.
And some of us have ugly pasts that don’t like to stay in the past. If this doesn’t bother you, then have fun. But remember, if he needs fixing, it’s not up to you to do that.
Also, are you looking to date his ex too? I think not.
You’re Set in Your Ways (And So Are They)
Let’s face it—you know what you like, and you’re not as willing to compromise on certain things anymore. That’s empowering, but it can also make dating harder if your routines or values don’t align. Merging two well-established lives is trickier than it sounds.
Does he want dinner on the table at 5 whereas you don’t mind eating later? These things may seem small and cute now but could create big problems later down the road.
Are you open-minded enough to pick your battles wisely?
Fear of Getting Hurt (Again)
By this age, your heart has probably taken a few hits, and that can make you more guarded. It’s not that you’re bitter—you’re just cautious. Letting someone in again can feel risky, even if you’re craving connection.
And being cautious is a good thing, especially in this day and age, but you’re gonna have to open your heart up a little. One day. Eventually. No?.
You Might Feel Invisible
A lot of people—especially women—report feeling “invisible” after a certain age. Society tends to glorify youth, and that shows up in dating. It’s frustrating, because your worth and appeal don’t disappear at 50—they just get overlooked more often.
We’re competing against Botox and fillers and losing the battle.
Trust me when I tell you that you’re not invisible. Your perfect the way you are and nothing compares to you. Period.
Adult Kids Can Complicate Things
If you have adult children, or if your potential partner does, they might have strong opinions about your dating life. Some may be supportive, others might resist. Some may try to compare you to ‘mom’ and some will hate you right off the bat.
Blended families can be super difficult. Do you have to put up with his kids? Do they live across the globe or in his basement?
Make sure you find out if the kids are gonna be a problem.
Trust Takes Longer to Build
You’re more discerning now, and that’s a good thing—but it also means it can take a lot longer to fully trust someone. Past betrayals might make you extra cautious. Trust isn’t automatic anymore—it has to be earned, one small step at a time.
And this goes both ways. Are you willing to put in the time to gain trust?
You might really like this article about women having trust issues.
Health Can Become a Factor
This might not be romantic, but it’s real: health concerns can start to play a bigger role in dating after 50. Whether it’s your own needs or your partner’s, physical limitations or medical conditions can affect how you connect, travel, or even just spend time together.
Can you handle all your potential partner’s medical issues, or can he handle yours? As we get older, health concerns tend to pop up out of nowhere. Are you ready for that with a partner?
If health issues are a concern, you may want to skip dating after 50.
Sex and Intimacy Change
Desire might not look the same as it did at 30—and that’s okay. Hormones shift, bodies change, and sometimes ‘the drive’ isn’t quite up to speed. You may have a high drive where he may need a kick start (or a pill) to get started. Can you handle that?
Communication is key here.
Or maybe you need magic cream or more initiating on his part. Whatever the case may be, you guys will need to talk that out.
You might really like this silly fun short I created about magic cream.
Fear of Losing Independence
You’ve built a life that works for you, and bringing someone into it can feel like you’re losing your freedom. Sharing your space, your time, your routines—it’s a big shift. The fear of becoming too dependent or losing yourself in a relationship is real.
It’s important to remember to stay true to yourself and the things that bring you joy that don’t need to be shared with anyone. If you find John is a little clingy on date 1, either set boundaries or walk away.
We need our space!!
Dating Can Feel…Awkward
If it’s been a while since your last first date, jumping back in can be nerve-wracking. Do people still do flowers? Who pays? What do you even talk about? The whole scene can feel unfamiliar and a little uncomfortable at first.
Are you mentally and emotionally ready for this? Can you be yourself and be open-minded too? I know, it’s a lot!
It’s Easy to Get Discouraged
A few bad dates, or weeks without a match, and it’s tempting to throw in the towel. The highs and lows of dating can hit harder when you’re older and have less patience for nonsense. Staying hopeful takes real effort.
I’m of the mindset that if you just put it out to the universe, exactly what you want, it will show up.
Also, staying true to who you are not settling for less than you deserve because you don’t want to be alone is kind of important too!
Do You Share Goals, Dreams, Hobbies?
You might want companionship but not marriage. Or maybe you want to travel, and they want to stay home. After 50, aligning lifestyles can be trickier because everyone’s got their own version of what this chapter should look like.
Make sure to be clear on your first date exactly what you want and don’t want, what your likes and dislikes are and what the non-negotiables are. The latter is super important!
Don’t settle, babe.
There’s Pressure to “Get It Right”
You might feel like you should know exactly what you want by now, or that this relationship has to be “the one.” But love isn’t a race. The truth is, you’re still growing and learning things about yourself in this second chapter of life, and it’s kinda confusing!
That also means you’re learning about what you want and don’t want in a future partner and it’s totally different from what you wanted 30 years ago.
There is no perfect person but there is someone who is perfect for you so don’t give up if you really want to find true love.
final thoughts on dating after 50
Dating after 50 is challenging and can be exhausting but try to have fun with it. I think it’s important to first set clear intentions with your date. Let them know exactly who you are, no lying, and relax and enjoy.
Life is short and for some, we don’t want to finish this journey alone.
Having companionship can add value to your life, as long as he is right for you. Always stay true to yourself and your values.
Oh and never give them your banking info! Ha!
