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.

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