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Should You Date a Former Cheater?

Whether or not you should date a former cheater is a complicated question that depends on lots of factors: how long ago the person cheated, what the circumstances were, exactly how you define cheating, and so on. It’s true that infidelity is common in almost every culture, whether a person has a history of cheating or not. But the short answer to the question at hand is a simple one: If you’re considering dating a person who cheated on someone in the past, then you should be careful.

Of course, there’s no guarantee that someone who’s never cheated will remain faithful. But keep in mind that it may be more likely for a person who has cheated before to cheat again. That’s not an ironclad rule, but it holds up often enough. And regardless of what the circumstances were in the person’s earlier relationship, you will always know that the deception took place. That knowledge may be tough to keep out of your mind…and out of your relationship.

If, however, you decide to consider dating someone who has a history of cheating, then at the very least make sure that you ask these important questions.

Does the Person accept Responsibility for his or her Actions?

This is a great place to start. If the person you are interested in has made mistakes in past relationships and admits to them, and also acknowledges that these poor choices hurt the people he or she cared about, then that is a good beginning. Assuming that you believe that this person is sincere, this acceptance of responsibility demonstrates a certain amount of self-awareness and is also evidence of a working ethical system.

If, on the other hand, the person makes excuses for his or her actions, blaming others and denying any fault in what took place, then that is a major red flag. Sometimes there may—and we stress the word “may”—be extenuating circumstances when it comes to infidelity. But even in those cases, the person who cheated still made a decision not to remain loyal to the person with whom he or she was involved. And that fact needs to be acknowledged and addressed in a meaningful way.

Has the Person Learned and Grown from the Experience?

This question focuses not only on accepting responsibility but also on overall maturation. In order to trust this new person in your life and enter into a romantic relationship with him or her, you need to feel confident that this person has taken steps toward relational maturity. Accepting responsibility for what happened before is certainly part of this. But in addition, the person also needs to be able to explain to you how he or she will be different in your relationship, and what changes he or she has made to be loyal and remain true as you two build something new together.

Has the Person Experienced some sort of Transformation?

Once again, we want to urge you to be cautious as you consider dating a former cheater. But keep in mind that transformative experiences do occur in people’s lives. These often allow them to become whole new people who interact with the world and treat other people in completely different ways.

Have you become convinced that this person has experienced some sort of genuine transformation—perhaps as a result of a spiritual awakening, a significant life event, or some sort of therapy? If so, then you might be more open to the possibility of a relationship. Again, you need to see convincing evidence that the person is sincere when he or she tells you about this transformation, but assuming that you do see that evidence, you might decide to lower your guard a bit and ultimately trust that person.

Are you the Kind of Person who is going to Worry About Being Cheated On?

The earlier questions focused on the other person. But what about you? Are you the type of person who can just forget about a past scenario, putting all current doubts out of your mind? Or will you always wonder whether your new partner is being true? That kind of insecurity can eat away at the foundation of a relationship, creating obstacles to genuine intimacy between you. If you are worried every time the other person is a few minutes late, or if you find yourself wanting to check his or her cell phone numbers or read his or her emails, then this might not be the best relationship for you at this point.

What do your Instincts Say?

When you listen to the voice inside you, do you feel that this new person is trustworthy? Do you sense that even though there have been past indiscretions, the person is true and reliable? Or does something within you say that you would be making a big mistake by trusting this person? This is one of the most important signs to pay attention to as you make your decision.

If you answer the questions above and find yourself believing that this former cheater will be honest and honorable in a relationship with you, then you may decide to give it a shot. But if you think over all that you know about the person, and little (or big) doubts continue to nag at you, then trust your instincts and move on.

Regardless of which direction you go, make sure that you take care of yourself. Guard your heart, and find someone to love who will love you back and treat you the way you deserve to be treated.