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)”

  • Matthew and Stephen: there is a serious issue in today’s relationship landscape with which ALL my female friends – both single and married – have struggled. I would like your take on it: male insecurities and whether or not they “feel like a man”. This issue has been faced by women of varying income levels, social status, physical attractiveness, single and married. In play with this fundamental issue are several “catch 22’s”, for example: the man wants to be the “provider” but doesn’t have an income to support it; the men want a woman who relies on them, but women cannot surrender their self sufficiency to placate a man’s insecurities; the men say: “sure you want me, but you don’t NEED me”, and the women are left baffled thinking: “yeah – that’s WAAYYYYY better. What’s the problem?”. It’s always the same problem: male insecurities ruining relationship harmony. It has happened to EVERY woman I know. It’s a massive issue. What say you?

    1. This is absolutely correct. Most men are not attracted by 30 year old women who have their life together. They seem too independent. They rather want to date/get together with girls who need them financially and emotionally. This is absolutely the main issue today.

    2. Thank you for this comment! I TOTALLY agree!! I m 34 ys old single woman and almost all the guys that i’ve met are insecure at all levels! Its a serious issue!!

  • I have started this expansion this year, and I am meeting a ton of people! I am part of two pretty big groups. No romantic relationships though. :/ It can still be tough to find, even when all of the pieces are there.


    1. this is because the role of women and men have been destroyed.. women have taken the ‘ i am independent and have 2 degrees’.. the men like myself can not be bothered trying to compete with the masculine energy the vast majority of women now project ..

      1. Why compete ? Why not just enjoy what someone else brings to the table. I would love to find someone with similar interests. Someone to do fun things with. Outdoor sports going to eat traveling. I always try to find someone with interests but don’t seem to meet many people that like to do anything but sit home. That’s fine here and there but not all the time. I grew up going on weekend getaways and would love to enjoy that with someone.

    1. Brett is correct. The main issue I see is modern feminists. Women don’t want to be accountable for anything and want it all. Men and women are different period and now no one wants to define what a woman is. Why do women expect a man to pay on a first date? Men want someone sweet and that doesn’t have a body count if 30+ dudes. Women just show up on dates expecting free meals without bringing much feminine energy or attributes themselves to the table. Or men value looks which now with blue hair and glorifying being obese does wonders for that.


    Great article, thank you Stephen! Maybe it’s just me, but I like the way you write because it sounds like we were just having a conversation over tea and you were giving me advice ond dating. It’s just very heartfelt. Thank you.

    I am, however, already in my 40s – never married, no kids and my boyfriend of 4 years broke-up with me 8 months ago. I wish I can say it was a good break-up, but it wasn’t.

    Though I am already in my late 40’s, people say that I look like I am in my late 20’s or early 30’s, which, I will be honest, feels very affirming. I like hearing it.

    Also, I also feel young and have the energy and the playfulness of, well, actually, someone in their teens or early 20’s. Long story, but I lived a sheltered life and didn’t start dating until I was 40. My ex is 10 years younger than me and people actually think that he was dating someone 10 years younger than him. We both liked when people say that. :)

    My ex’s theory on why I look and “think young,” is because I haven’t been “jaded” or have enough baggage and bitterness yet and that I am a genuinely happy and playful person. He said that one of the things he truly appreciated about me was that I have the looks, energy and playfulness of a girl in her early 20’s, except without the immaturity and whiny-ness.

    My biggest dating issue is that, I know that I am supposed to be dating men around my age group, preferably older (which is what my friends believe I should be doing). I should be looking for more matured men, who are stable, monogamous and want “that stability too.”

    Okay, I have no problem with that. However, men my age or are older, and I feel so ashamed admitting this, look really old, even for their age. It is hard to feel attracted to them. I tried. I forced myself to feel attracted. It really, really is very difficult for me.

    They are also very serious and has the “retirement-thinking” mentality. Most of them are bitter and have their own baggage – starts conversations with “I don’t want drama in life.” Well, uhm, duh! Who wants that? And, who starts a conversation with that? Sorry! I don’t mean to be sarcastic.

    I’ve also done a lot of personal and spiritual development for over 10 years now. I constantly work on myself, so I am attracted to people who do the same.

    I work out, not because I want to lose weight or want to look good. I work out because I really enjoy it. I teach Zumba. I do a little bit of belly dancing and body combat (it’s an aerobic form of MMA with music. I love it!) and I do a little bit of kickboxing too. I just feel very Lara Croft-y when I punch and kick people. It’s really fun!

    The men who are in my age group, who I am attracted to, have the playful spirit, does a lot of personal development work, can carry interesting conversations, are… married. :(

    I know I need to get out more with friends. I know I have to cast a wider net, but uhm, which part of the ocean? :) I mean, uhm, the “matured fishies,” don’t move that quickly and maybe easier to catch, but what if I don’t like what I get?

    Sorry, this is a really bad analogy. :(

    Or, maybe I should just accept the fact that I should just be okay with dating casually (I don’t mean intimate encounters. Not a cougar either. I don’t like that word, sounds very predatory) and just enjoy the company of men I am attracted to.

    Uhm, help? :)

    PS. If I am just being arrogant here, please just let me know what I need to change about me. I want to learn. Don’t pull any punches. I can take it! :) Almost literally actually! Thank you!!!

    1. Most women over 40 say they receive compliments that they look so much younger. Well society had taught men to be polite to always say a woman looks younger by at least 10 years. As if people are concerned with how old you or me look. The are concerned with their own lives.

    2. OMG and I thought I was the only one!

      I am in my 50s, told I look younger, take care of myself. The men in my age bracket or older look just awful. Not only do they not try but they don’t have any energy about them either. Old-fashioned too.

      I mentioned this to my therapist, and she said she had heard that from other patients and that we all should just suck it up, that was the way it was.I’d rather date younger men who are divorced and have had their kids.

      What city do you live in? I’m in DC.

    3. I so can relate to your writing. I’m halfway my 40’s and faced a lot of trauma in my life. Apparently I look a lot younger also, which I think doesn’t help me in meeting that one person. I tend to be attracted to older men and was lucky to find men who were also young at spirit. But all of them brought me into a toxic relationship. They are being paranoid over me doing things behind their backs etc. But always turns out they are the ones cheating and lying, but putting all the stress on me. I refuse to give up on love, but I feel that I’m stuck between the traditional image of relationships that society taught us and the modern ways of dating and being in a partnership. So sorry I live in Belgium. We could have gone for a coffee. Or a cocktail

    4. Jade
      If you want men in your age group who are physically and mentally very active and look years or even decades younger than they are, have you tried US Masters Swimming?
      You will naturally need to enjoy swimming, and there is a learning curve if it is new to you.

  • Hi, What to do if you have no peer group? The few single friends I do have don’t have the same interests as me. I completely failed at online dating, so now I am at loss for options. It shouldn’t be so hard.

    1. Girlfriend. I hear you. I’m in exactly the same boat, haven’t met a new guy outside of work in years.

    2. Hi my friend. You need to go out and make friends. Go to your favorite hobbies and while you’re there, talk to people! Go to the theater, cinema, Galleries, Bookshops, Gym, etc. and actually talk to people. Say things that are interesting, exchange numbers to go to similar events and voila, eventually you can expand some of those friendships and get into new groups of people.
      Best of luck to you. :)

    3. Meetup.

      I live in a city of about a million people, and there are thousands of Meetup groups. I could go to a new one each week and never get bored! Also of note, that unless it’s a very female orientated group, the scales tip in favour of male numbers. (Upon research I’ve read it’s because men really target this site as a means to meet people. Who knew!).

  • I have never really given this much thought but when in my twenty’s I had a date almost at any when when I wanted to.The kind of date’s most people would dream about.Wite table clothes ,wine and a Gourmet dinner and then off to a silent and cozy bar pretty much made for couples. Then I ended up in a couple long-term relationships my last one was with a man that was 17 years older than me and I could see even in my late thirties what might happen and that was what’s going to happen when he dies and I’m in my 50? And that is exactly what happened now I’m 54 and I’m having a hard time getting readjusted to being single and wanting and needing social relationships and yet I find myself completely happy almost being alone in my apartment at most times. I have a man that I absolutely adore and even though we live five and a half miles apart and he is extremely busy he always finds time to come and see me and spend a night or two. In fact we are almost like teenagers living our life backwards and being good kids not hitting too involved in the lovemaking Department. But that is exactly what I would like and also just adore his personality his set of morals his boundaries and such things of respect this is what attracts me so highly to him because that actually what I’ve been looking for all my life is a gentleman. Let’s face it I want to find the two of us eventually together we have our private jokes S&R private pillow talk and common case in art I’ve even been a model for him he is a photographer. He has a strong faith in God he takes also good care of his parents that are still alive and live an hour or so away. His life is very full and I know he’s highly into me but the question I have is how much is he into me this guy has made me feel so much for him that I want to be exclusively his and I wonder as many things as he does for me does he want me to be his exclusively. Yes he says all the guys things but I’ve been reading endless name 2 with Matthew hussy. Plus living a distance apart makes AZ house our hearts grow fonder fonder I have learned how to shorten my text and also say little things that makes him want more. But how do I know if I should invest more it’s like I am in my twenties again which I had so much fun then I didn’t realize the Clock Was ticking and all of a sudden I ended up being 54 I have lost major weight and have become very muscular and slim and call but I have a body that looks better than when I was in my twenties this all happened before I met this man I decided to change my life for the better health-wise so I look upon this as a lifetime change not just a year or two. My question is this man has been married twice his last one was for only six months they were a disaster and I have never been married, but find myself desperately wanting to marry this man. I love his work I understand him doing major craft fairs and I’m okay with that due to the fact I’m fairly well have been independent and most of my life so I can handle but lonely at times but I don’t want to end up being a spinster I want to be close and married and to support our love for one another. I want you know more about him each and every day I want a family his sisters brothers parents Etc I want his flaws and also his drive for life itself, and also what we have created together amongst ourselves. But how do I get him to commit and take one more Chance on marriage. He has had horrible disaster and have had to what away from his marriages and literally lose absolutely everything he has built his life upon. Now I’m not financially rich but I find myself not wanting anything from this man because I am finding him being the man I have absolutely praying for and lived for even though I am 54 he is exactly what I have dreamed of and yet I want nothing from him except for his love even if the relationship was to go bad yes I would walk away with a broken heart butt I would not take anything of his or financially that was his whatsoever because that is the type of person I have found myself all through life to be I would rather have love and a slice of bread and a heart that beats next to mine than anything else in the world. I truly believe that love does conquer all. I don’t just want to be a passerby and I don’t feel like I have missed my ship I feel just the opposite it’s like I’m living my life backwards in time I got all that messy stuff out of the way when I was young and I have found that I care and love the people of this world so much even the cranky and the horrible people because there’s a place in life that these people exist for a reason because they’re not I go. But yet I would give them the last slice of bread a shower or whatever else as long as I find that they are not a threat or just after one thing. That is not the love I have ever envisioned. But this man fits every directions that I have dreamed about since I was young. He has all those qualities of family the privacy of love the touch that we dream about xcetera xcetera. We now have been closed 4 almost a year or at least three-quarters of a year we practically Gmail each other short messages everyday just to see how each other is doing and we have our private little jokes and and poke’s at each other it’s like he’s my Jessie James and I’m his Bell Starr, My Fuzzy Bear, and I his Sweet Pea and yet I find not wanting anything from him except his admiration of love in our lives. And though he says that his plate is full I see his scaredness from his past marriages. I just want to be in his Circle afamily and our love and respect for one another? Is there room can there be room for us to be together or should I move on and look 4 another relationship. Can I get him to commit he appears to me to be highly in love with me but I myself have that question and doubt’s weather he finds space in his life for me? the last man I had I was with close to 20 years and believe me we sustained ourselves on love respect and admiration. And yes there was times I wanted more commitment and time spent with me and the last couple years we had just that. Before that that is exactly what I wanted was at least 2 years that we could go and camp and dig our hands in the soil and make beautiful gardens and that is exactly what we did unfortunately I thought he should live to 99 but he died at 66 and at least it went quickly he was in so much pain from the cancer I have kept the picture from him for 6 years now and last year I swear he told me look I want you to be happy and you need to live out the rest of your life doing just thought that it was time to let him go it’s been 6 years now and it was almost instant when his eyes told me that but that’s when I met the man of my dreams but just like all other people we come with our own garbage and our own heartaches and we take them as lessons learn the hard way. That seems to be human nature. We seem to be Our Own Worst Enemy. Time in time again. I always know it is true love that when I desire nothing from a man accept the closeness of two hearts coming together. But since men think so differently then women I definitely now from what I have read from you and watch for me I am in his marriage category or should I say the top of his love list besides his family. He treats me like I am a queen and I should be treated as such. He is such a gentleman that any mother would be so happy to have their child come out as such. My question is is there anything I can do 2 speed along and also to get him to commit and marry me? Am I doing something wrong? Am I giving him too much am I not giving too much. I envisioned this before I Tangled with a man that was 17 years older than me but yet we were two peas in a pod and when we met it felt like we’ve had known each other for thousands of years, our hearts were definitely drawn towards each other because of that reason. And no one thing that when we were the poorest we were the richest.And yet I want to be able to show him how true this can be. We have so much fun together and come so far this far. I Don’t want to lose him by any means or make him feel like he could do better, or want me to move forward in finding someone else.That his life is so full he has no time for a relationship. I find this one of the reasons why men and women are having such a problem’s meeting the man or woman of their dream’s. Thought cell phones are wonderful they have been slowly breaking us humans apart we spend to much time on are phone’s tell to much on are phone’s etc,etc. We are social by Nature.So on one hand they are Great and yet they are the other side of the sword it is just as sharp. We do not need a friend and even if you due people are Leary of the other because we don’t need friends, if we have a cell. So here is the Big question? How do I get him to commit, and I become a Bride and for us to become as a team and to keep that twinkle in are eyes for one another for the rest of are lives. Yes that is rare I admit but it is not impossible. I have seen that kind of love before, and it always makes a person wonder. How do they keep that flame that creates the same feeling that they had for one another as the day they were married. After children hardships and all the bad thing’s that happens to us through a lifetime. Why do a few grow closer while other’s pull apart. I think truly why I have kept myself apart from the one’s in the past that asked for marriage but I didn’t feel it like I do know. Every love we have ever had in our lifetime is diffrent from the last. I ha e had relationships that where just visual,and some of those were fantastic. Other’s have a slow comfortable compassionate feeling. Others have felt fast and fun and busy which is also as good as the others. But the one I find in now is like he is the one I have prayed for all of my life and with such such a different feeling then I have ever felt before. Please I am asking how do I get him to commit and find out the absolute pure love and gentleness that I have for this man the compassion the not needing just his love.?

  • What about fifties? I’m in my fifties. People in their fifties are a lot different to people in their fifties many years ago. I don’t look my age and mix with people of all ages. I’m surprised age has even been mentioned here. Disappointing.

  • sounds like i need to leave my, kinda big leap but i like the idea :) let’s see.. i’ll try to consider that and think about it.
    but yeah, why not?

  • Finally!! It was like I’ve been thinking and worrying about but I can’t talk about with my friends because they are part of the problem… Reading this let me set things in perspective as if I was talking with a friend who is going trough the same, which isn’t at all what’s happening with my friends! Thank you so much!

  • I’ve been single for 7 years! I can’t find a boyfriend! Guys just don’t want a relationship with me. All my friends are in relationships, long term commutes getting married and having babies.
    I can’t find single friends either. At 29 single people are a rarity.
    I swear I will die alone…or give up and go for a man I’m not interested in because of the fear.

  • Interesting article. From a single Male in early 40’s we are in the same boat. How and where do you meet single women that your interested in? I often see a group of older women out for dinner and drinks. As a guy your thinking it’s a girls night out. It’s not the time to approach someone. What else do you like to do? And when and how do you like to be approached is a mystery to me. Often I read women want a confident guy. I get it. Everyone is different though and if you have wants you have to deliver them too. I love doing anything new and are pretty active. My coupled friends not so much. At least not on a regular basis. Hanging out with young people can be fun. But interests vary and I’m tired of partying. There’s a lot of other things I’d like to do with my time.
    I don’t enjoy online dating and would love to meet someone naturally but have to accept this is the times and get in with it. Like others it all just seems too hard. I want to invest time in finding someone but the effort, enthusiasm and energy it takes when your older is emotionally draining. Then when you do meet someone your both coming in with baggage as everyone does. Are you compatible? Are you attracted to each other? Like each other and what you stand for? The odds don’t appear to be in our favour. Like everyone here I wish I had the answer.
    I’m not willing to give up on finding love.
    What I’ll keep doing is everything I can! Hobbies I’m interested in and maybe try ‘meet up’. Even making friends with other people similar could open the door to other potentials.
    Will try to use advice in post and go out with single friends.
    There’s got to be some amazing woman out there for me! Where are you? P.S I’m a bit of a Catch.
    All the best ladies.

  • Guys you are amazing, but unfortunately now guys doesn’t wants meet in an organic way even if you have friends, I crossed for a depression because I broken up with a guy who says was divorced and at the end he takes the desission to back with hes exwife… not enough y with that I realised he maybe lied just becuase I told him I want a relationship, after all .!! And still am alone, am pretty, fun, I feel happy with my life , and I feel proud about my self even with all of this .. I found my self alone again, didn’t find any motivation more that breath to live because I tried all and every day I dream and I wish wake up with my love … why girls needs to do almost a master to meet a guy ?? They are sooooooooo special sooooo complicated??

  • Easier said than done I’m 40 ALL my friends are married, have kids, in relationships or gay. Do you expect me to go out and find “new friends” to then help me find a man? Where should I go to find these “new friends” I’m past going to clubs and bars and actually none of my circle do that stuff anymore. I’ve been single now for 7 years…

  • In order for this to work many people has to do it. Because if people in their 30s don’t go out.. if you begin to go out.. who are you going to meet? People in their 20s.. I guess I have to go out to the supermarket or places where I have a chance to find older guys…

  • Tinder. I’m a single woman in her late 40’s who opened a profile two months ago. Oh well… I’m going on dates every week and have already met a love paramour. I’m not kidding. It’s the best invention since peanut butter. My advice: keep your married friends (because good friends are not easy to find), feed and nurture those good friendships you already have and go on tinder.

  • In in my 49 soon to be 50 in Single now Been married for 13 years . My ex husband. cheat on me with other women and have kids .. I divorce him ..

  • Great advice and oh so true! The problem is though, how do you acquire single friends in your middle years? It’s not that easy! Yes, I agree that we mustn’t stagnate, but finding people who want to go ‘out out’ at 50 is no easy task.
    Great article though

  • I agree with ‘M’’s comments below! However, I would entertain and enjoy a man who would approach me if I am out with my girlfriends on a night out. The tricky part of this whole situation is that it seems both men and women feel apprehensive in making a move and bottom line it’s the fear of rejection that keeps us at bay from each other! Too bad his post was from 2018!! “M” I’d invite you over my way with a smile and half-wink ! Thank you for sharing perspective from a man’s view!

  • It’s not finding someone that’s difficult. The offers are there. It’s about not having much time left and being with someone who’s on the same page. I just wasted 10 years with someone who decided they could do better, wish he had decided that 5 years ago. Now I want fun and a bit of romance. Not just a booty call

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