From May to December: Reflections on Dating Older Men

url1For the past four years or so, I have been exclusively dating older men. Some just five, or seven, or nine years older, and some… well, significantly older than that. And really, when I say “older men,” I mean those who are (roughly) 15+ years older than me. Because I find that it is at around the fifteen year age gap that there becomes significant difference in the divide. Men who are ten years older than me may not have grown up in the nineties per se, but they were teenagers, and so they remember that decade with a similar kind of naïvety. They hadn’t quite learned not to love terrible music, and they still felt that patterned leggings on girls might be acceptable. Men who are fifteen years older than me were at university in the nineties, and that makes a difference. Going on from there, as would be expected, it seems to be the case that the larger the age gap, the more significant and numerous the differences. Although that’s not to say those differences are always negative.

I started dating older men shortly after I had my first sexual experiences – with boys my own age – which I found to be intriguing, but largely unfulfilling. I already knew I was attracted to men much older than me, but it took a little while for me to find my footing, and in retrospect I am quite glad I lost my virginity to a friend my own age, as it meant figuring things out together; there was a sense of comradeship in our explorations. But of course, as is the case with so many of my dating choices, it was my budding inner kinkster that demanded I admit my liking for older men, and eventually I realised that one way or another, benefits and pitfalls all, this was going to be something I’d have to deal with quite a lot.

Since that realisation I have been involved with around ten older men, the age differences ranging from fifteen years to around thirty five, and whilst many of those relationships may not have lasted long, the ones that ended, ended amicably. Not only does this give me a nice platform from which to look back, but it leads me to my first point:

Provided I don’t cause it, my relationships with older men have been wonderfully drama-free. For me, that alone is enough to recommend these connections. That I am still good friends with at least five of them, and in touch with a further three, seems testament to how sensible and reasonable older men are. I know it seems obvious and perhaps overly simplistic, but I don’t think we really appreciate just how wonderful it is to be with someone who doesn’t sweat the small stuff, and won’t run a mile when you need to bring up emotional subjects. Of course, this isn’t the case with all older men, – likewise, not all younger men run when the going gets tough – and I have had a couple of experiences with older men who were just naturally nervous or fickle, but generally speaking, men in their late thirties and over have a better handle on what’s important, and are more likely to show respect. As an example, in the past year I have parted ways with two men in their forties/fifties and two men in their twenties/thirties. The older men kindly, clearly, and respectfully spoke to me about it; the two younger men simply stopped calling, leaving me in the dark for a week or so to figure it out for myself.

However, on the other side of this, being with an older man means I have to take on a little more responsibility. Whilst age doesn’t seem to lessen sympathy, there is only so much bullshit an older man is likely to put up with. It seems to really be true that the older you get, the more precious time becomes. Of course, I feel that people should always strive to be reasonable and sensible with their partners and not waste time, but being with someone older does make me more aware of what is important and what I’m just making a fuss about.

So far this has all been detail; aspects of the same kinds of issues that would arise no matter how old my partners are. This is just variation on humanity, really. So let me press a little deeper.

Something that has come up a couple of times, and always carries a lot of weight, is the fact that older men have had more time to accumulate ties. Whether it be children, or work, or friends, the older the man, the more likely he is to have something he is responsible for. In many ways, I’ve found this to be really wonderful. It adds to what I’ve said above about older men being sensible and responsible, but it also adds a sense of care and affection – and added care can be a very lovely thing. However, I’ll be honest: these kinds of responsibilities will always limit the amount of time I get to spend with my lovers. To a certain extent, this is a price I am more than willing to pay; but I won’t deny that it has led to the end of several otherwise wonderful connections. If you don’t have time for each other, you just don’t have time. Although I think there is also an argument to be made that in this fast paced world, we simply have to make time for the things we want, it’s not an argument I’ll make here, and ultimately, as with almost everything, I assess on a case by case basis. But in the end, my point still stands: as people get older, time gets more precious, and whilst I may still be a priority, I’m likely to be one of several. So I have come to terms with the fact that having a full time, together-more-often-than-not relationship with a much older man is less likely to happen than with someone closer to my own age.

But none of this is what really breaks my heart.

Here’s the thing: having decided to date older men, I began to come across married men, and I apologise if this sounds crass, but for the purposes of this argument, married men – and I mean men in monogamous commitments – fall into two camps: happy and unhappy. It really is that simple at times. Dating older men, I don’t come across a great deal of happily married men. But I do meet a lot of unhappily married men. In fact, the first older man I ever dated seriously wasn’t married, but he was in a committed relationship, living with a woman, and he left her; not for me, but I was something of a catalyst when it came to that decision. In this case, unable to break those final ties, he retreated, and six months later they were back together, and I was receiving a much too long email explanation I really didn’t want. I’m not saying this kind of situation never works, but that experience taught me to be wary, and I’ve heard more sad stories than happy ones when it comes to this kind of thing. I think situations in which a person leaves his or her long term partner for someone else are actually quite rare. Despite the number of divorces, my observation has been that people seem to leave because they need to leave, not because they have met someone new. And I always work from the assumption that a man is not going to leave his partner for me, because those situations can become very difficult, and I don’t particularly want to tear apart a relationship that might, for all intents and purposes, actually be quite good on the inside.

And yet… there is something utterly heartbreaking about falling for unhappily married men. Because I don’t think I would ever ask a man to leave his wife for me, no matter how great our own connection. I might suggest – and have – that a man open up his relationship with his wife, to allow him the freedom for both, but the truth is that we still live in a very mono-normative society, and that suggestion has yet to be taken with anything other than suspicion and uncertainty, which I understand: it is quite a high bar to clear if you’re in a long-term, monogamous relationship. So this leaves me in an awkward situation. The truth is that a lot of those men – twenty or thirty years older than me – have settled down. They are married, or have been; they often have children, and there may be something noble in staying in those relationships, but from where I stand, it can also be quite tragic.

Let me digress for a moment: there is, of course, another option. In many cases, I don’t necessarily have to choose and I don’t have ask men to leave their wives. In many cases, I could just consent to affairs. The truth of the matter is that many men are willing to cheat on their partners. They have justified that to themselves, and, after all, you only live once, and life is short, and really, we can only do the best we can whilst we’re here. However, I, personally, won’t help men cheat.

A year ago I went on two dates, with two different men. Both were married, both going behind their wives’ backs in order to meet me. I fucked one of them, and when it came to the other one… I couldn’t. We scheduled a second date, but I cancelled beforehand. And for a while I wrestled with my conscience. Because a part of me really does believe that life is too short to deny yourself happiness. But another part of me can’t help siding with their wives. Women whose lives are equally short, and who, if they knew, might very well feel that they are wasting their time. It is true, that with the two men I met last year, both had a sense of purpose about the way they pursued me. They weren’t simply open to connections with other women if and when they happened, they were purposefully seeking people to sleep with. Once again, I think this can be justified by the fact that life is short, and I can’t bring myself to really pass judgement on those who do cheat, but for myself, I can’t justify being a part of that deception either. It just doesn’t sit right with me, nor the way my affection manifests. And so I decided not to get involved with men in monogamous, committed relationships. Although, even that is proving to have some grey area!

But, back to my point. Knowing that most men are not going to leave their partners for me, it can be incredibly heartbreaking and frustrating, watching them go through the motions of an unhappy marriage, when I feel sure that if they left, if they started again with me, they would be happier. I know there is a part of this that is slightly ridiculous: how do I know that I could really make anyone happy? But still – it’s hard.

And to some extent, this is yet another symptom of our youth-loving, aesthetic obsessed society; and that makes me truly upset. I’m trying hard not to generalise, and there are always exceptions, but I do happen to know a handful of men who simply feel they couldn’t find anything better than what they have; men who really feel that most women don’t find them attractive any more. And who’s to say, if these idealisations didn’t beat us all down, that these men would be any more likely to leave unhappy marriages, anyway. But it feels like such a ridiculous detail to have standing between me and men I truly, utterly, adore. And what’s worse, in a society that seems to live so much online, flirting and compliments fall from people’s fingertips all-too-easily, and therefore are just as easily dismissed as playful and insincere. So when I say I find someone attractive, when I tell a man I want him, how is he supposed to tell the difference between my honest words, and the screaming of thousands of people vying for attention?

Time, commitments, priorities; I can make my peace with these kinds of obstacles. But when I say “I want you,” and it’s brushed off as idle, online banter? That tests my patience and breaks my heart. Because it is such a fucking stupid reason to reject happiness.

  12 comments for “From May to December: Reflections on Dating Older Men

  1. 26/04/2013 at 18:53

    What an interesting and beautifully written piece. Our culture dislikes cross-generational relationships, which is sad since the different generations have so much to teach and learn.

    • Harper Eliot
      27/04/2013 at 00:35

      Well, on the one hand it is sad yes… but then again, if our culture liked these kinds of relationships more, they would hold less interest for me.

  2. LexiRose
    27/04/2013 at 02:56

    Your post struck a chord with me.

    I had a relationship with someone 30+ years my senior when I was 20. He was much more settled, balanced, his life was arranged as he wanted and I struggled to find a place I’d fit. And so I bowed out.

    Last year he had a heart attack and I had an emotional reaction that led to me reconnecting more personally. However, there still wasn’t space for me in his life to the degree that I wanted and so I had to back off.

    On the other side, I’ve met many men, and one in particular who seems more honest than most, who are unhappy in their relationships, but choose to stay with them.

    Their decision is their own, and I’m thankful that they’re honest enough to admit to their situation. But I do feel for them.

    Again, one in particular seems unhappy, and I’ve had to work to disconnect and reconnect on the friend level because although I know they are unhappy as they are, they would be equally unhappy with me at this moment in time.

    It’s hard, when you feel a connection with someone, to back off and take the friend role because you know, in your heart, that whilst what they have isn’t what they want, they need to experiment and decide what it is they want.

    And I’ve found this in men from 18 to 58. If you’re with somebody for a long time, another person may give you the incentive to leave or think, but it doesn’t mean you want to be with them.

    Because we can connect with people nowadays through so many different mediums, its easy to form a bond, and to think that bond means more than it does. Sometimes, you’re just a friend who gives the means to escape.

    And it’s that juggling between friends, friends with benefits, men with benefits, men who only want the benefits… That’s what I struggle to get my head around.

    And having (thanks to the Internet) a pool that ranges from 18 to 68, I don’t think it’s just age that influences it. I know 26 yr olds who act like 50 yr olds and 66 yr olds who act like 18 yr olds.

    It really is about each person and how the two of you react/interact

    • Harper Eliot
      27/04/2013 at 18:29

      Actually I agree. I think almost everything I’ve written can apply to people of any age and gender. That’s part of the reason I wrote it so much from the “I”, which is something I tend to avoid: I prefer to use a more distant tone, usually. But, for this, I felt it was so rooted in personal experience, that it needed to come from me, and not just my observations. And – like I say – I agree with you: the only thing I would add, is that everything I’ve mentioned in this article has struck me more with older men. But it is just my experience. There’s also a lot to be said for the fact that every person is different: so regardless of age, it’s always going to be a unique experience, in good and bad ways.

  3. 27/04/2013 at 14:28

    It is such a stupid reason to reject happiness. For myself, I was also attracted to older men, and had less drama and more actual care and concern in those relationships. And then my last two, long term relationships, have been with men younger than me, and I am dissatisified with the self-centeredness, and video game playing is a huge issue (a new drug of escapism). I don’t believe that I would have the same issue with older men.
    I know many unhappy married men who feel that they can’t do better, and it is sad as the foundational reason to stay in a relationship. However, if the other partner doesn’t know, it is not a reason to stay but still go out into the world searching for better. Glad you can empathize with the woman also stuck with a now unfaithful man.

    • Harper Eliot
      27/04/2013 at 18:32

      I really do empathise with the wives and partners; like I say, I find it really hard to justify it to myself, and I don’t like doing it. It’s just not respectful. As for the young men vs. older men thing: well, I think both have their benefits and pitfalls, but at the end of the day, I’m attracted to what I’m attracted to. And that’s just how I work. Which is a shame, sometimes.

  4. James
    27/04/2013 at 19:43

    I found your blog fascinating and even moving and look forward to reading more from you. I am one of those older men you talk about who have relationships with younger women. I recognise much of what you say in my experiences, but not everything.

    When I was an immature youth I and the girls I went out with were mostly unable to talk properly about feelings and about needs and the ending of relationships was invariably very messy, angry and confusing. I would often be left with no real understanding of what had gone wrong.

    I’ve been single, after a long marriage, for 20 years. I’m 62. My lovers since then have ranged from age 20 to age 50, the most recent being the oldest. The 20 year old and another aged 28 both ended our relationship by simply not returning calls. No explanation was ever offered. The other relationships, which were all with women over 30, ended reasonably amicably, inasmuch as whilst there may have been a short hiatus while we sorted ourselves out, we then remained friends. I’m going to the cinema with one of them, aged 36 now I think, next week and we’re great mates.

    I have been able to talk about feelings and needs with most of my lovers and that makes such a difference. Gone are the anxieties of youth. If there’s something we want or that we’re unhappy about we talk about it openly and directly, rather than dropping hints or saying nothing and resenting.

    The major difference between my experiences and what you’ve talked about is that in probably about half of my relationships with younger women the woman has been either cheating on her partner or ‘on a break’ while she decides if she wants to stay in a long term relationship. As a result I have often been what I have described as a transitional lover. I seem to be a safe bet, someone who will offer affection and a positive ear, and, perhaps most of all, someone who won’t rock the boat. In other words I won’t ask for too much and I won’t rat on her when the relationship ends, as they all have.

    Typically, my relationships last between 3 and 6 months and then, almost invariably, the woman returns to her partner or commits to him if she hasn’t separated before. One decided to have children. Another decided to get married. At one point I started to think I was performing a public service.

    Two weeks ago I ended a 6 month relationship with a beautiful and very sexy woman of 50. She had divorced her husband a year ago but was still living with him as he had nowhere else to go. He knew she was seeing me. We had a fabulous physical relationship that had a lot of potential and we had a lot in common intellectually and socially. There were differences, but generally we were great together. And then I started to get stronger feelings. It was almost like being on a grotesque see-saw. The closer I got the more she withdrew. I knew she wasn’t ready for any kind of commitment; she was honest enough to say that from the start. I wasn’t looking for commitment either, in the sense of living together or (God forbid!) marriage, but I did want something more and I didn’t think it was ever going to happen. So I probably panicked a bit (is it possible to panic a bit?) and felt I had to end it. I miss her a lot. We don’t see each other or talk, but I’m hopeful that when the hurt settles we will be friends.

    I’ve gone on too long and probably rambled. The difference I was alluding to earlier is, I think, that for me it’s the younger woman who is often busy with work, or family, or a partner, whereas the older man, me, has his life organised well enough to be able to make time for the things I want to do and the people I want to spend time with. Maybe it’s simply because in your case the relationships have been between a woman in her 20′s (?) and a man in his 30′s or 40′s, 50 at a push, with a family and a career to focus on. In my case it’s been women from 20′s to late 30′s (mainly) seeing a man over 50 and now 60 who knows what he wants to prioritise.

    I haven’t found out in any depth what happened to most of the woman who returned to their partners, although I know one of them has had 3 children, so hopefully she’s happy. But I fear for the long-term happiness of most of them. As you do for some of the men you’ve met. They all seemed to be unhappy, despite very full and often successful lives.

    Best wishes.
    J

    • Harper Eliot
      29/04/2013 at 22:18

      Thank you for your insight, and your lovers sound like they’ve been very lucky to meet you.

      You know, it’s funny, because when I look at my life – work, school, blogging, podcasting, big immediate family – I wonder how on earth I have time for relationships myself. But I do think, for me, it’s because when I’m with someone I make them enough of a priority that I will make time for them. I don’t judge others who don’t, but personally, I like to spend time with the person I’m seeing: it makes me happy, and I think that’s good for everyone. I can’t remember exactly what in your comment prompted me to think of that, but somewhere in there it did. Oh, it must have been about your experience of younger women being busier.

      Oh, and the “at a push 50″; my most recent partners have been well into their fifties. So, it’s not so much of a push any more.

  5. 29/04/2013 at 14:37

    Thank you for writing this, I really enjoyed the honesty of it and the insight. The discussion on married men in general is so spot on. For the most part, I avoid married monogamous men. It’s not because I feel it is wrong or I judge them, it is because, at the end of the day, they cannot provide me with everything I would like in a relationship. Only getting to talk to him during certain days or certain hours, puts a damper on things, at least for me it does. Limited to when and where we can meet, how we can act, constantly having to be careful, always in hiding, it just begins to be too much. I know that these things are what makes affairs “exciting”, but I guess being open and honest and in a polyamorous lifestyle myself, just makes it cumbersome.

    • Harper Eliot
      29/04/2013 at 22:20

      Yes, I completely agree. The hiding and being careful,etc, feels really cumbersome to me too. And there is certainly that aspect to my decision, but… since I’ve discovered that no one – single, monogamous, or open – seems to have much time these days, the fact that married men don’t have time seems less significant. But I think the hiding is still very poignant.

  6. 10/05/2013 at 21:55

    Tough question….from my personal experience and that of my friends, I would say that about half of women have interest in an older guy. My friend just married the love of her life, who is 10 years older than she is and she couldn’t be happier.

    • Harper Eliot
      08/06/2013 at 22:43

      I think we are generally socially and culturally taught that men should be older then women in a relationship; I certainly grew up feeling like that was right (despite the fact that my Mum is five months older than my Dad). But there is a slight difference between ten years and thirty-five…

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