Once a Cheater, Always a Cheater?

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You’ve probably heard someone say it before: “If he cheated once, he’ll do it again.” Everyone loves a good generalization, don’t they? If someone cheats once, will that person usually cheat again? In a nutshell, people who cheat will usually cheat again unless they suffer a major consequence for their behavior.

Cheaters who experienced a serious consequence can learn from their mistakes.

For the vast majority of men and women, sexual monogamy is the expectation and highest priority. When someone is unfaithful, the cheater will usually only change if their partner either breaks up with them or takes at least a month-long break from the relationship. Following a breakup or relationship hiatus, the cheater is forced to sit with all of his feelings: guilt, self-admonishment, embarrassment, and sadness. It is precisely the experience of having to sit with those feelings – as opposed to going back to normal – that forces the cheater to take a hard, honest look at his behavior and to realize its cost.

Cheaters who are spared a serious consequence will usually keep cheating.

If a cheater cheats but ultimately gets away with it without any long-term consequence, why wouldn’t he cheat again? If a cheater is not forced to deal with his cheating, he will never deal with the underlying reasons that made him cheat in the first place. Accordingly, he will usually keep cheating.

It’s also important to understand why the cheater cheated. In other words, the cheater ought to know with specificity what motivated him to step out of his relationship and into the metaphoric bed of someone else. Why a person cheats, after all, may tell you something about whether he will cheat again.

If you are dating someone who has a cheating past, ask the following questions.

What made you cheat?

Regardless of the unique circumstances, there is always a reason why a person cheats, and it always has to do with a primary feeling. The main causes of cheating include anger, resentment, boredom, and loneliness. I don’t believe every cheater is a bad person. People begin relationships with the best of intentions, but it’s often not until deep into the relationship that people realize they have major emotional needs which are not getting met. For example, if Josh mistreats or takes advantage of Sasha, it is understandable – at least on a common-sense level – how Sasha could make a mistake and cross a boundary with a man who shows her attention. Was she wrong to cheat? Yes, but again, we must look at her selfish behavior in the larger context.

How did your ex treat you?

Just because you ask someone a point-blank question doesn’t mean that he or she will tell you the exact truth. Nevertheless, it’s important to ask because the answer will provide you with more information and because your current date deserves a chance to share his side of the story.

How would you handle the situation if you started feeling the same way again with me?

If the former cheater comes up with a trite, one sentence response, don’t let him off the hook easily. If he says, “I would just never cheat again,” that’s not an answer. Below I include a word-for-word sample of how you can have a conversation about cheating.

A sample conversation to have with the one who cheated:

Josh: “I don’t know why I cheated; I think I was just really unhappy.”

Sasha: “I know, but you could get unhappy again, right?”

Josh: “Not that unhappy.”

Sasha: “It’s understandable why it would make me nervous that you cheated before. I need you to convince me why you wouldn’t do it to me in the future.”

Josh: “I just wouldn’t. I would talk to you if I’m unhappy.”

Sasha: “I’m going to ask that you do a few different things if you feel that way with me so that you don’t let it get that bad. Would you agree to talk to some friends if you get unhappy or suggest relationship counseling to me?”

Josh: “Yeah, I guess so.”

Sasha: “Okay, and what else can you come up with? I keep asking because it’s important to me.”

Do you see what Sasha is doing in this conversation? She is holding him accountable and setting up a verbal contract – not to not cheat, but to handles his feelings better so that he doesn’t end up cheating!

Don’t ask too few or too many questions.

Sasha asks about five questions related to his cheating. In other words, she doesn’t live in denial and let him off the hook with a question or two; she also doesn’t beat the issue to death or demand that he talk to her for hours about the issue. Ask a few questions which get to the heart of the issue, and then take some mental time of your own to sit with his answers. After you’ve had some time to think, you can decide whether you believe he probably will or won’t cheat on you in the future.

About the Author:

Dr. Seth is a licensed clinical psychologist, author, Psychology Today blogger, and TV guest expert. He practices in Los Angeles and treats a wide range of issues and disorders and specializes in relationships, parenting, and addiction. He has had extensive training in conducting couples therapy and is the author of Dr. Seth’s Love Prescription: Overcome Relationship Repetition Syndrome and Find the Love You Deserve.


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