Perhaps you're already going to take issue with this post, based solely on the headline, because my use of the word "when" already implies that it is okay to date a known cheater.
I think the conventional wisdom here is that if you know somebody is a cheater, that means they've demonstrated a propensity to indulge in that behaviour, which means that you can't rule out the possibility that said person will likely indulge in that behaviour again. The lesson of the parable of the farmer and the viper, it seems, is the prevailing view: s/he's damaged goods, and if you trust him or her to act differently, you have only yourself to blame when you get bitten.
But allow me to throw a monkey-wrench into that theory: lots of people actually do cheat. The last time I saw the stats on this, it was somewhere around 30-50 per cent of marriages that had experienced some kind of adultery. The numbers are staggering, and that's just self-reported adultery. Additionally, we have the sobering statistic that 10-15% of all human beings are sired by a man other than whom they believe their biological father to be. That figure, of course, is skewed to the low end by the number of abortions that terminate pregnancies that are (potentially) the product of adulterous relationships, which is one of the most oft-cited reasons women report for getting an abortion: to prevent their partners from finding out about the affair.
Basically, lots of us are adulterers. And more importantly, we ALL have the same propensity to cheat in the right circumstances. That's because our bodies are genetically hard-wired to exploit opportunities for reproduction with those that our pre-conscious brain finds reproductively fit. Monogamy, on the other hand, is not hard wired. That's something that we discovered to be a viable reproductive strategy UNDER CERTAIN CIRCUMSTANCES.But if circumstances change (say, the ubiquitous road-trip, alcohol-fueled fling that the partner will never find out about), that natural propensity to exploit the reproductive opportunity will ignite. And often, in such circumstances, cheating happens even by those who would before and after describe cheating as something they'd NEVER do. Why? Well, because in many ways and in many circumstances, our pre-conscious brain is exercising its decision-making power before the conscious brain is even aware of what's going on. I think we've all been in this circumstance, viz. doing something you know is probably a bad idea, your conscious decision-making power coming in and out in its losing battle against the overwhelming emotions and sensory bliss that you're experiencing.
So, I think what this all means is that for you to hold another person's demonstrated propensity to cuckold against him or her is to ignore your own latent, as-yet-undemonstrated propensity for same. The difference is that you've never been tested. And obviously, there seems to be some room for conscious choice. Sometimes in flagrante delicto, you'll suddenly come to your senses and put on the brakes. But just up the pressure to a sufficient degree and the problem arises yet again.
Bottom Line: Cheating of this kind always remains a possible pattern of behaviour that ANYBODY, under the right circumstances, will indulge in.
Of course, I'm talking here about single instances of adultery, not about protracted affairs. With protracted affairs, the cuckolder cannot claim that his or her conscious decision-making power is hijacked by desire and emotion. Here, the person is making the conscious decision to carry on a pattern of deceptive behaviour. Of course, the same reproductive drives are promoting the behaviour, but in this case, the person is ratifying this unconscious drive with a conscious decision (1) to indulge, and (2) to indulge for a extended period of time.
Here, my advice is that it's okay to date somebody who you know to have carried on an adulterous affair only if you know that s/he has turned a corner. Meaning that s/he regrets the adultery, not just getting caught.
For my money, what this (hypothetically) means is that she understands that adultery is a losing reproductive strategy for her. But not all of you, I suppose, are inclined to choose your partners based on their understanding (or lack thereof) of the evolutionary, genetic basis for their reproductive actions.
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