“He’s perfect.”  

“She’s amazing.”  

You know, the person you just started dating. You’re asking the questions, and you like the answers you’re getting. Until you ask them that fateful question: “Did you cheat on your spouse?” 

You value honesty, so you appreciate that they’re truthful. But your heart sinks because you don’t like the answer: “Yes.” 

But is yes an automatic dealbreaker, especially if you’ve been cheated on before? You always thought it would be, but now that you’re faced with more than a hypothetical, you’re wondering if the adage is actually true, that once a cheater, always a cheater. Like most else when it comes to dating, my answer is that it doesn’t have to be. 

Dating dealbreakers are sometimes rules that can be broken, including a history of cheating. 

I’ve been in the business a long time. More than 30 years, in fact. And what I’ve learned is that to avail yourself of all opportunities, of all dating prospects, you sometimes need to live in the gray. In other words, you’re going to have to evaluate every situation for what it is. Which means not only will you want to listen to their story about why they cheated, but you’re going to have to read between the lines when you do. Then decide if your dealbreaker is a rule you’re willing to break.  

But before I get started about what you need to listen for, I want to be clear that I’m not advocating you settle. If after a discussion about why the person you’re dating cheated on their spouse, you don’t like what you hear, by all means, move on — as fast as you can. My advice is simple: give the person a chance to explain their past behavior, and why you should give them a chance. 

What you should listen for when deciding whether to date someone who has cheated on a former spouse. 

As we all know well, life is complicated. With that in mind, if a dating prospect explains they were cheating due to a specific circumstance you find is not only believable but also understandable, it’s OK to give them a chance. An explanation that resonates with one person might be completely offensive to another. Everyone has their own barometer about what’s acceptable to them and what isn’t. Figure out what yours is.  

The best explanation for cheating has little to do with the reason and a lot about regret.  

Some cheaters will have no explanation whatsoever other than to say they made a mistake. That they regret what they did and feel remorse for their behavior. These are often the best kind of people to date, despite their past cheating.  

That’s because they’ve processed the situation. They understand what they lost as a result of their actions, how they hurt people they love and loved, and how they hurt themselves. These are the people that would never want to cheat again. For them, they know there would be too much at stake. This is someone who, if you’re up to it, could be worthy of a chance.   

Final Thoughts... 

Cheating is one of the worst ways to hurt a partner. It’s a betrayal, and it can be life-changing for all of those involved — the cheater, the spouse, their children, extended family, and friends.. If you’re in a relationship, I don’t recommend engaging in this behavior, whatever the circumstance. Instead, I always suggest exiting the relationship in a transparent way.  

That said, no one can change the past. And I do believe people are capable of growth and chnage. That people are capable of remorse. And that human beings are capable of having compassion for someone they never thought they would once they know the full story. Therefore, the question you have to ask yourself when confronted with someone who once cheated is: “Am I at least willing to listen?”