When exactly is it that most men hit the point of peak entitlement, non-listening, world-class dullards and yet, despite being more closed off to the outside world and the most out of touch they have possibly ever been, feel perfectly comfortable being outlandishly demanding?

It’s a slow process, perhaps simmering within them for their entire lives.

A friend and I discussed her observation (and I agree) that many men we know (mostly men in their 50s) are mind-numbingly boring, selfish and self-involved conversationalists who are so lacking in self-awareness that they don’t realize they have monopolized the one-sided conversations they start with the most boring of rambling. My friend is a social woman and tries to engage everyone in conversation, which I admire but also cringe at, knowing she will end up in more than her share of these time-suck monologues. I have no small talk wizardry at my disposal so avoid this kind of stuff as much as I can. Most people are boring, in the end. I have often found myself in challenging and awkward social situations, where I overcome my aversion to idle chitchat – at considerable pains – and want to almost congratulate myself that I kickstarted a conversation, only to hate myself for bothering minutes later when someone starts talking ad nauseam about himself, his stodgy perspectives, insipid opinions and lifeless hobbies. Conversation thus becomes tedious, drudgery… and work. And the monotony is wearisome.

But these guys were certainly not born this way? Before they hit 50, and found themselves on the loose in the world as single men again for the first time in years, they did manage to get married and have families.

One friend told me recently about how hard marriage is. The man she fell in love with was gregarious, outgoing, curious, adventurous – always looking for new things to try. And these were the qualities that attracted her, the things they had in common. He was the life of the party and could win anyone over because he’s so talkative; in fact, he dominates every conversation with his stories and opinions. He had life experience and adventures to share, though, and stories with which to regale even the most reluctant listener. With each passing year (click the link for Gavin Ewart‘s “Short Time”, brilliant poem on self-deception) though, he has grown less adventurous, more closed-off and closed-minded. But he still turns on the charm in social situations and dominates the conversation. For how long, though, will it seem charming, as the ratio of adventures/new stories dwindles versus the urge to dominate, and eventually tyrannize, the conversation?

I started wondering if this is the trajectory of the 50-something man. Not every man has been quite as witty or engaging as this friend’s husband, but is there something to the idea that as these guys’ experiences, influence and curiosity diminish in breadth, reach and frequency, everything about them becomes more limited in scope? And for men who dominate conversations, they reach this period of just-beyond middle-age and do not realize they aren’t the life of the party. My theory here could be way off, but isn’t there a correlation here? These guys, if they ever had “it”, have lost it – and they and their wives are no longer in the same place… for the same old reasons. One changed, and the other didn’t.

What gets me, though, is that these 50-something men often get divorced but then don’t even question or evaluate how it all broke down. Could it have anything to do with the fact that every time they opened their mouths, they showered their wives with routine, interminable selfishness? And if that assertion is anything close to true, wouldn’t it make sense that they might recalibrate before striking up conversations with new people (whether colleagues or dates or potential partners)? I keep running into this exact scenario – sometimes being met with obliviousness (I could walk away and these men would continue to babble), sometimes being met with absolutely foul, sour and hideous behavior and insults (and here I mean real nastiness). Either way, this demographic – maladjusted pricks and dicks (of any age) – isn’t one I am keen to be around.