The Biggest Difficulty Of Dating In Your 30’s (And 40’s, 50’s and 60’s)

Stephen Hussey

You’ve crossed over past your twenties. Maybe even thirties, or forties. You’re single. You’re in a great place in your life to meet an incredible guy.

It’s taken a while to get your act together, but now you’re able to objectively look at your life and feel quite pleased with what you’ve made of yourself.

You worked hard through your early life to build some kind of meaningful work. It took sacrifice, effort, and focus – but you took the time and found a career that keeps you, if not always 100% motivated, at least interested for now.

Now you’re thinking about where you might meet a guy to share it with. Out at a party? A night out? Somewhere fashionable with friends on a Saturday afternoon? And suddenly the worrying truth hits you: Do I even do those kinds of things anymore??


You realise that your social scene these days consists mostly of dinners with OTHER couples, or quiet nights in with flatmates watching a movie, or even just weekends catching up on errands and being in your apartment. You enjoy these things, but you also realise that it’s been a long time since you even met any new guys, let alone a great one.

And this is the danger of getting older: We cease to have a life that gets us meeting NEW people.

What Happens in Dating After 29

Part of this, you’ll be glad to know, is all your friends’ fault.

Those now-coupled-up friends from high school or university are only making this more difficult. They have little interest in parties, going out, the kind of things single people do when they want to meet people.

Quick as a flash, from the age of 29 onwards you started to see more and more friends announcing engagements on Facebook. Some of them even had babies. Really early babies (at least, it seems that way to the rest of us who can’t even imagine being married yet).

Now you’re listening to your former single friends talk about first mortgages and building their nest with their family, and you’re wondering how you’re going to meet a guy when being “out on the social scene” has suddenly become the last priority on all your friends’ minds.

The danger isn’t being single in your early thirties and forties. The danger is feeling like you’re in this period of your life adrift, without support – leaving you to cling to friends who only want to pull you further into secluded hibernation with them in their cozy relationship nests.

Getting Balance In Your “Dating Peer Group”

So what’s the solution? How do you jump off of this treadmill of hanging out with the same people, in the same places, at the same obnoxious dinner parties.

It’s time to diversify your “dating peer group”.

If you limit your friendships to married people, it’s hardly surprising that your social life becomes nothing but an endless sea of seemingly happy couples. Yes, I’m sure they have a “great single friend” they’d love to introduce you to, but in the meantime, instead of waiting around to see if that lottery ticket turns out to be a winner, it’s time to cast a wider social net.

Say “yes” to those friends who get you out of the house on a Friday night and saying “no” to yet another offer of spending an entire weekend hanging out with your best friend and her fiancé.

By all means, give your coupled-up buddies an hour or two for lunch on a Saturday afternoon. But then have somewhere cool to go in the evening where you’ll ACTUALLY get to socialise and be in proximity to people you’re romantically interested in.

I’m not recommending you ditch your friends. I’m recommending you have more variety in who you hang out with.

Maybe it’s acquiring a few younger friends who are still focused on being out there and having fun. Maybe it’s pursuing your own interests and hobbies so that you expose yourself to a whole set of new people who can bring you into a new social circle. Maybe it’s calling up those other single friends whom you’re less close to but who are probably more up for being “out there” meeting guys than your married friends.

I’ve learnt in my most stagnant dating periods that my biggest mistake was often just hanging around people who had no interest in being single and dating. This meant I spent many a sociable hour at perfectly nice dinners with couples, but at the cost of being out at the places where single people tend to flock.

Just as in any other area of life, when it comes to dating and finding love, your peer group matters. The people you spend your time with will determine the amount of guys you meet on a weekly basis, and therefore determine your love life.

You don’t choose your family, but you do choose your friends. What no-one tells you though is that you have to KEEP re-choosing them depending on where you are in life. Make sure you choose some balance.

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52 Replies to “The Biggest Difficulty Of Dating In Your 30’s (And 40’s, 50’s and 60’s)”

  • I’m in my mid 30’s and besides the fact that it is difficult to find a single guy my age or a little older (who I actually want to date), these guys usually tend to be divorced with kids who are not interested in relationships, but having fun. Ironically it is the younger men who are ready to date seriously, start a family etc.

  • Hi Stephen, thank you so much for the post! You are highly appreciated!! It really makes sense to choose the circle of people to hang out with! I actually have friends who are couples and we always go for a dinner and drinks where I don’t really meet other single guys. So I have to think about my single friends and saying “ yes “ more often to their proposals for going out and socialise. Thank you once again and have a wonderful weekend! ✨✨✨XX

  • lol this is so me. i do hangout with married couples with kids and a few of my friends that are engaged. it does get seriously lonely especially when im already 41 turning 42 in a few months. My brother send this post to me because he is married and i guess he wants me to look for someone lol! well this year is going to be a great year for me because im starting a new business with training and meeting people in these seminars. Hopefully i meet my other half! i wish everyone luck and i hope you find the one! Also focus on being positive and on what you want to accomplish first in your life!

  • Bloody Hell.

    I was just reading back on everyone’s comments and it’s gone back to 2016.

    I knew I had read this article before. It is a well written article Stephen and great advice.
    I did take this on board at the time.
    But to be brutaly honest I put myself under emmense pressure to be on a out of control dating busted wheel that’s rolling down a cliff and it’s just gone off the edge.
    Believe me!
    I tried and tried and tried I dated lots of men. It drove me to drink.( I am Irish I am allowed to say this)

    So, since I have now fallen of the edge I now see this from the bottom up and realise that I was never kind to myself and felt I never deserved a happy life.

    I spoke to myself that was dark and horrible. But that is over now. I have accepted myself and I feel so much happier. For once I truly understand myself and when the right guy comes along, and he will.
    At least I wont be putting on a stupid bad show of myself. I am gonna be living my best life with a fabulous man that is on my side as much as I am on his.
    Single and fabulous Cat xxx

    Ps whats your views on what I said ?

  • Thanks for the tips! I’m a Male, and a Hopeless Romantic! It seems I’ve struck out half of my life! I’m choosy, and I’m aware that’s part of the Problem, but I’ll take Beauty, over “Everybody likes her, she and her mom are so much alike, she’s a little thick, but if you two fall in lothey cheat on me, they’re never allowed back into my Comfort Zone, ever again!ve, she’ll lose weight!” No, not for me! If

  • Thanks for the tips! I’m a Male, and a Hopeless Romantic! It seems I’ve struck out half of my life! I’m choosy, and I’m aware that’s part of the Problem, but I’ll take Beauty, over “Everybody likes her, she and her mom are so much alike, she’s a little thick, but if you two fall in loveshell lose the weight…if they cheat on me, they’re never allowed back into my Comfort Zone, ever! No, not for me!


  • I wish this would be this easy. I’m in my mid-30s and befriending different kind of people is just not a guarantee for any kind of outcome. I’m also a musician, so dating a musician colleague I am working together with on a project is neither an option for professional reasons (if it turns out good, yay!, but if it turns out bad you have less opportunities). So in my point of view, in theory this could work, but when it comes to practice, I don’t think it’s a good solution.
    Also, another huge problem with dating above your 30s is that you don’t necessarily have the urge to have a relationship, nor wanting to get into casual dating. The scene looks like this: you either get a very serious guy, who wants children (who knows, maybe you don’t), or you get the f*ckboy who pretends to be an easygoing nice guy, and of course you have the relationship-traumatized guys who don’t want to commit. So your choices are kind of limited.

  • I’m in my late 40s, divorced 13 years, no kids, in good physical and mental health. I’ve put in a lot of work to determine who I am and what I want.

    Men are highly interested in dating me, but none want monogamous, long term relationships. They haven’t done the work to know who they are. They’re either newly divorced after thirty years of marriage or have been divorced a few years and both types enjoy the freedom of dating more than one woman at a time.

    I’ve done the meetups for outings. I’ve tried making friends with other single women, but they either are focused on their kids or big into bars, which I’m not. I’ve tried dating apps. It’s a meat market, regardless of how clear you are in your profile (following Matthew’s rules) that you’re a high quality person seeking more than a hookup.

    I’m not unhappy being single. I like my alone time and independence. I’d love however to meet a good man who I share common interests with and who wants a relationship too.

  • Hi, thank you for your advice. I’d like to add another perspective, if I may, that I’ve not yet seen directly addressed.
    I’m 51, divorced with three kids. Most my age are empty nesters or soon to be. I married and had kids later in life, so I’m about a decade behind my peers with life stage stuff. I was on dating apps for a while but kept hearing the same reasons from men as to why they didn’t want to date me. The first reason I kept hearing from men is they didn’t want to go back and deal with young kids again. I totally get that. And that’s without even discussing that two of my three are on the autism spectrum. I have yet to meet someone who can handle that. I get that too. Honestly. The second excuse I heard from men my age and older was that I run too far and they can’t keep up with me. I have a lot of energy and love to run. I joined the local running community. I really enjoy the outdoors and running ultra-marathons! But, that seems to turn men my age off. I would date younger men but there still seems to be a taboo about younger men seriously dating older women. I say this because I’ve met younger men several times only for them to change their minds once they learn my age. Would love to hear you and Matthew address some of these very real challenges for us older ladies. I have high but not impossible standards and don’t want to have to dim my shine in order to date. In the meantime, I’m enjoying my life and have some races to train for and places I’d like to travel to. It would just be really nice to be able to share the journey with someone else. I never expected to grow old alone. Thanks for all that you do.

  • Thanks Stephen! I’m 65. Everyone thinks I’m in my late 40s. Most of my girlfriends are in their 40s. My problem is meeting guys who are in my age bracket who don’t look 70+. Most Guys stop looking after themselves after 50. I do go out with a lot of 40 year olds who freak when they eventually find out how old I am and pretty much end the relationship. I don’t mind younger men.
    My second problem is that I’m now on an old age pension and live out in the country. Going out anywhere is expensive. Petroleum costs keep me at home a lot. Finding a new partner seems like finding a unicorn. How about some advice for dating after 60 please. We have our own challenges.

  • There’s this kind of thing I’ve been seeing a lot lately. No one wants to make an effort. Like, if you don’t live three miles away you’re too far away. Or if you want to talk to them, just one time a week, immediately you’re needy. Or they only call you when it’s convenient for them, not you, and now you’re frigid. I don’t understand the balance, or if there’s any. I feel like every guy, I’ve met so far, just want a booty call and that’s all.

  • “Those now-coupled-up friends from high school or university are only making this more difficult. They have little interest in parties, going out, the kind of things single people do when they want to meet people.”

    – Except, I’ve never hung out much with married friends. I’ve been single so long, I no longer have interest in doing the kind of things single people do. After 20 years or so it gets old. :)

  • I’m 59 and divorced Most of my friends are married and a lot of other single women my age have either soured on men and think there are no good ones out there or they have just given up and decided they will just be alone. They also don’t want to stay up past their bedtime. Well I’m not dead yet. I’m vibrant passionate and want to get out there and have fun, go listen to music, dancing, sporting events etc… I’m online dating but it really is tough. I’ve met some nice guys that just weren’t right for me. I’m dating one now for four months so wish me luck

  • This post a lone could be a good potential for people to connect. I see so many comments of individuals with the same mindsets and for me this is a good start

  • Try meetup. Great social circle enjoy doing what you enjoy. In every city. I’m in Perth, West Australia with a thriving social life meeting new people all the time.

  • I blog quite often and I genuinely thank you for your content.
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  • I’m in my mid late 30s. Never been in a relationship never thought I would find ,meet and or see a man that would also interested in me as well until a couple months ago. It was day before supper bowl, I was at the pop section of grocery store and there he was. He was looking at me with interest and smiling but not in a creepy way just very sweet smile and look at me. As I was going to the other side of the store, I saw him again at another section of the store, he again smiled and he laughed ( the kind of laugh a guy has when he again sees the woman he likes). I hope I have another chance to see him again, next time I will not be afraid of rejection, I will definitely talk to him.

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