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UPDATE: I have a second article on this topic… Check out part 2!

When a woman in her late 30s is dating, there’s a fair chance she’ll date some men in their 40s. Many of these men will be on the dating scene having previously been married; if anything, divorcees are the dating norm nowadays.

But if you are the aforementioned woman and you find you are dating a fella over 40 who has never been married, or at least in a co-habiting, long-term marriage-equivalent relationship, is it always that case that there is a reason for his eternal singledom?

This question reminds me of a rather perceptive quotation from the terrifyingly-accurate fictional doyenne of dating, Bridget Jones:

Will find nice sensible boyfriend and stop forming romantic attachments to any of the following: alcoholics, workaholics, sexaholics, commitment-phobics, peeping toms, megalomaniacs, emotional fuckwits, or perverts.

You see, modern dating causes the smart girl to ask WHY her current squeeze has never managed to make it work with a woman. I should add, at this juncture, that I’m sure there are similar questions relating to 40+ women on the dating scene but, never having dated any women, I only feel qualified to speculate about the male of the species. I’m sure there are equally damning perceptions from both sides of that particular fence. Feel free, dear reader, to add your experiences of crazy cat-ladies and such like in the comments section…

So. You’ve been on a few dates with Mr Could-be-right. But you’re asking yourself how he has managed to avoid a committed, semi-successful relationship thus-far and whether you should therefore be seriously considering him as a prospect? I suggest that you ask yourself whether he falls neatly into any of the following categories:

1. The Daniel Cleaver

Part-sexaholic, part emotional fuckwit, the Daniel Cleaver has never been married because, put simply, it would make it tricky for him to remain a womaniser. He likes, nay LOVES, women. But only ever on a temporary basis. He’s very charming, great in bed, knows all the right lines and can successfully convince you that he wants to find “the one”. But actually, it’s all about the chase and his enthusiasm wanes significantly once you start to demonstrate some sort of romantic attachment towards him. You can sometimes identify a Daniel Cleaver by the power of social media: his Facebook profile is locked down tighter than that of an MI5 agent, yet his status updates are “liked” by reams of women and rarely any men. If you met him on a dating website, the minute you ask him if you two can become “exclusive”, he’ll block you (claiming  that he has deleted his profile) so that you can’t see his dating activity. You get the picture.


2. The commitment-phobe

These are the guys who you might describe as serial-monogamists. They genuinely do want to find “the one” but regardless of how many well-suited women they date, the relationship never lasts. Almost always in this situation, she leaves him rather than him ending the relationship. He’s faithful, loved-up, and incapable of seeing his life any differently than he’s always seen it, meaning that to actually commit to a woman long-term is impossible, as it would change his life. The mere concept of change utterly terrifies him. This chap is not deliberately single; if anything, he desperately wants to be in a fulfilling relationship. But he subconsciously pushes against togetherness due to the phobia of losing some control, independence, sense of self, or the horror that is a woman who might leave the scatter cushions in the wrong order.

3. The workaholic

This is the man who defines himself by his job. His perception of himself is entirely based on his perception of his success at work. He’s more than likely well-paid and well-respected, and obsessed with demonstrating his success at life-in-general through status symbols. He’ll have a nice car, he’ll own a nice house, and wear decent suits. But his status-anxiety leads him to believe that work is the single most important aspect of a man and this leaves little space in his schedule for devoting to a gerbil, never mind relationships. Nuff said.

4. The star-crossed Romeo

Remember Romeo and Juliet? Their love for each other was intense, to the exclusion of all rational thought. Romantic? For sure. This chap has loved a woman with all his heart. He may even have been engaged to the love of his life but, whether through circumstance, ill judgement, or even by having loved a woman who simply did not return his love, he can never again find a woman who can match up to “her”. She WAS “the one”. She cannot be replaced. Just like Romeo and Juliet, it is tragic, heart-breaking, and in the end he dies alone. Quite probably through no fault of his own. Nobody ever said that life was fair.


5. The Pervert

Probably an unfair description, but as the Bridget Jones system of classification is working, I’ll stick with it for now. This chap will seem very “normal” until he gets you near his bedroom. You may even have been dating him for a little while (because obviously, dear reader, you wouldn’t get your knickers off on the first date, now would you?). But once the relationship turns physical, you’ll start to see increasing evidence of his, let’s call them “preferences”. Perhaps you’re locked in a passionate, post-dinner snog, when suddenly he refers to you as his “little bitch”. Or maybe you’re at his place looking for somewhere to charge your phone, when you happen upon his extensive collection of butt-plugs and handcuffs. Either way, you’ll know it’s time to take your leave when you get the feeling that he’s never going to get his kicks without a touch of deviance that is a little outside your comfort zone. Far be it from me to criticise anyone’s bedroom antics, but you can bet your bottom dollar that he’s never married because he’s never found a wife who is willing to explore his deviances (and “special toys”) for the next three or four decades.

Feel free to add to this list ladies. I’m sure I’ve only scraped the surface. Who have I missed?…