Once a Cheater Always a Cheater?

Once a cheater always a cheater“: It’s a phrase that can spark considerable debate within infidelity forums, where very few seem to take a neutral position on the subject.

Those who are firmly opposed to the idea that a cheater will always be a cheater tend to be those who reconciled with their cheater after an affair. It makes sense - they have chosen to move forward with their cheater, perhaps having found sufficient understanding and/or forgiveness of their cheater’s choices, or perhaps by adopting a hopeful and positive marital advocacy as their basis for their future with the cheater. It’s entirely contrary to their chosen path if they subscribe to the ‘once a cheater always a cheater’ viewpoint.

On the other hand, those who believe that a cheater is a cheater is a cheater are often firmly and equally entrenched in their own position. They believe that the only self-respecting way forward after an affair is to leave the cheater, even while being completely sympathetic to the egregious unfairness of it all. They generally take the view that cheating is not caused by an imperfect relationship (which it isn’t) but the result of embedded traits in the cheater - or even a psychological disorder- and that affair behavior will therefore repeat on a never-ending loop.

So who is right?

Well, both views have shades of ‘right’.

A Case Study - Kris Jenner

Once a cheater always a cheater ?Kris Jenner, the manager-mother of the Kardashian franchise, published a book that referenced an affair she had while married to Robert Kardashian. The revelations served as a story line in the reality show, Keeping Up With the Kardashians.

Her sexual and emotional affair with the much younger Todd Waterman was not unique in its anatomy (it’s worth noting that affairs are rarely unique in any material way). She was a very typical cheater and was (sadly) not unusual in her specific selections from the usual buffet of crappy cheater choices, including:

  • dissipation of assets (using marital funds to conduct the affair, buy gifts, and pay for affair activities etc)
  • introducing children to the affair partner and including the affair partner in activities with them
  • getting children to lie to cover up the affair

Her affair with Waterman resulted in a divorce from her husband when he discovered it. Jenner had planned to live a new life with Waterman but the relationship didn’t last (he cheated on her). It was during this time she met her current husband, Bruce Jenner.

Fast Forward 20+ Years

Whilst taking a tennis lesson, Jenner unexpectedly spotted Waterman on the premises. Did she leave quietly, doing what she could to avoid contact with Waterman?

Uhhh, nope.

She made her way to the clubhouse to engineer a ‘chance meeting’, exclaimed her surprised greetings, exchanged niceties, and gave him a hug before leaving.

The High

Did it end at the goodbye hug?

Uhhh, nope.

As she hurried away, she said (presumably to the film crew), “He looked like he wanted to talk to me. I don’t know what’s going on but I’m just going to wait over here for a second.”

Not surprisingly, she met up with Waterman, gave him some contact details, and engaged in a lengthy hug before tearing herself away. As she drove away, the almost giddy Jenner called her associate (whose email address she had given Waterman as a contact email) for a gossipy revisit of the encounter, punctuated with excited squeals and gushes, and a speculative and gleeful-sounding, “So you might get some steamy emails from Todd today.

The affair high that many cheaters feel, seemed to kick in quickly with Jenner on meeting up with her former affair partner. She seemed immediately and entirely absorbed by the encounter, the potential of that encounter, and the buzz she was getting from Waterman’s evident renewed interest.

Research by Stanford University’s Brian Knutson shows that just looking at the object of our desire activates neural signals associated with the release of dopamine (a neurotransmitter released during reward signaling) in the brain. Knutson’s research suggests that we don’t just derive happiness from attaining, receiving, or consuming the object of our desires, we also do so from anticipating it i.e. it’s not just eating the cake that makes us happy but also staring at it through the storefront.

Emma Seppala, Ph.D., The Chase

It’s the potential of an affair that gives a cheater that first, heady rush, and Jenner reacted to it as if she had been hooked up to a fast-flow dopamine IV.

The Unfolding Justification

The narrative that cheaters develop to justify or excuse their affair can be a mind-boggling example of creative license. As the affair looms and develops, the cheater tweaks and hones their rationale, adding pieces of ‘substantiating’ thinking or history to authenticate their reasoning for having the affair.

People mistakenly assume that their thinking is done by their head; it is actually done by the heart which first dictates the conclusion, then commands the head to provide the reasoning that will defend it.
~ Anthony de Mello

Jenner engaged in the same type of thinking in order to give herself justification to further pursue the encounter with Waterman. Her starting position was clearly that she wanted to meet up with him so her subsequent thinking and internal rationalizations were an exercise in conjuring up a pathway from where she was, to where she wanted to go.

She did tell her husband (Bruce Jenner) of the chance meeting (presumably because it was filmed and would be impossible to hide). This cleared her conscience and gave her room to claim that she was not engaged in anything untoward or underhand. It was a classic piece of scene-setting gaslighting, which she built upon as she explained her position to her husband.

She then made it clear to her husband that she had not given Waterman her own email address. This was offered as reassurance and additional weight to her ‘there’s nothing going on’ story, by implying that it was a distancing, safe, and practical solution to avoid intimate and/or secret contact with him. In reality, it provided her an ability to communicate with Waterman without Bruce Jenner’s knowledge, and co-opted a third party into the secrecy and development of the drama.

“I don’t feel like there was anything wrong with me sharing an email address with Todd. I’m not doing anything, or concealing or hiding or sneaking around.”

Her subsequent contact with Waterman through her associate’s email started a series of continuing interactions with him. The office became a safe place for her to indulge herself in the drama of it all, to giggle and share titillating pieces of her affair story, and gave her a cohort for speculation about Waterman’s intentions and feelings.

Her associate would read aloud the emails received from Waterman, agree a response with Jenner, and send that response on her behalf. This enabling behavior encouraged Jenner to use her as a confidante, but Jenner’s rationale began expanding as she started to justify why she should make contact with Waterman privately.

“This has been eating away at me”

“The more I think about it, the more I want to text him”

Once a cheater always a cheater ?“I feel like I have something to say - I feel like it doesn’t need to be said through email. There’s that little file up here in my head that still has his name on it and I don’t want to have any regrets.”

“I can’t sleep any more I really can’t - I just have to get it off my chest. I don’t want to have something that I really want to say to somebody and not have the opportunity to say, ‘This is what I feel like you did to me and this is how it made me feel’.”

Her to-camera explanations followed in the same vein:

“When I get overwhelmed I get really emotional. I just need to get this out of my head.”

“I don’t deal with things and I block them out of my head - the break up of Todd and I was so quick and almost cold turkey, and what I think I need right now is a little bit of closure.”

To her daughter:

“The guy cheated on me and I’ll never get over it.” (Oh the irony!)

“This isn’t somebody I met and knew for a week and can just brush off. I don’t look at it like I’m playing with fire. I look at it like I have a few things I’d like to say to him. I got divorced! I left my husband for this guy!”

Unresolved ‘issues’ from an affair over 20 years ago was her rationale for meeting up with Waterman again. Despite her daughters cautioning her, they too were drawn into the affair drama by their mother.

Jenner did eventually meet Waterman (picture below) without her husband’s knowledge, and there were reports of a renewed affair between them.

Once a Cheater …

Jenner and WatermanKris Jenner’s story exemplifies cheater-thinking. It’s characterized by a sense of entitlement to explore sexual and/or romantic relationships outside of (but in addition to) the primary relationship, self-serving justifications, and a disregard for the impact of her choices on others.

It’s important to understand that cheating is a mindset, not simply a question of opportunity and/or discontentment with life. Infidelity is not caused by failing marriages, imperfect relationships, childhood issues, or failures in the faithful partner. Cheating is the result of a cheater giving themselves permission to cheat, shoring up that choice with a list of their dissatisfactions as ‘reasons’ for why the affair became acceptable to them.

The excitement and titillation that affair drama creates is what sustains an affair, in part. The secrecy, the sense of getting away with something illicit, and the safe cocoon of mutual validation … it all peaks to a crescendo of drama that, fueled by raging hormones, is an enticing and undeniable draw to cheater-thinking.

It’s been over 23 years since I even laid eyes on him but suddenly it feels like yesterday.

~ Kris Jenner

… Always a Cheater?

All too often cheaters skate by on smooth declarations of regret, and claim that their cheating days are behind them. They might further claim that they have learned their lesson, that they didn’t understand the damage that their affair would cause, or that the affair was a one-off brought on by a perfect storm of circumstances in life that wouldn’t repeat.

However, does that stand up under closer examination? Logic leads us to conclude that if the mindset and world view that was in place when they cheated hasn’t changed, then the same mindset and world view would allow them to cheat again.

We cannot solve our problems with the same level of thinking that created them.

~ Albert Einstein

We should understand that dissatisfaction is not the cause of cheating. If it were, then we would all be cheaters. Furthermore, we would be all be serial  cheaters until such time that we were living a self-defined (and self-measured) ambrosial and perfectly happy, satisfied life.

Cheater-Thinking Can Resurface

Cheating requires a certain mentality and belief in the individual’s right to live a more perfect version of their life, regardless of any ethical consideration of their circumstances and how their choices impact and affect others.

Kris Jenner quickly hopped from her affair with Waterman to her marriage to Bruce Jenner, and it seems strikingly obvious that she did none of the necessary work that probably would have avoided the whole Waterman-revisit drama in which she so gleefully engaged. Unfortunately, the damage in the wake of her choices both then and now are being played out in front of the cameras in both her husband and her daughters.

It’s interesting though that Jenner seemed to genuinely believe she was acting appropriately, calmly rationalizing the situation. This is common with cheaters.

Yes, of course there are those who very clearly engage in an affair because they can, and because that’s what they want to get into. However, there are so many who believe that their thinking and subsequent conclusions are reasonable, rational, and the same conclusions to which anyone would arrive given the same circumstances. The affair escalates from relatively innocuous behavior without them being fully cognizant that it was in fact starter affair behavior. “It just happened” characterizes that particular model of thinking.

It didn’t seem that Kris Jenner understood what was happening in her own thinking. She did initially seem to genuinely believe that she was seeking closure (not the re-opening of the affair), that she was being respectful of her husband (by not giving her own email address or phone number), and that she was not encouraging Waterman’s attentions (by having her associate communicate with him instead of communicating directly). She wasn’t willfully and deliberately capering around delighting in a newly engaged affair.

It highlights how many inch towards an affair, tweaking their thinking and rationale after every interaction without really seeing how this slowly progresses them into muddier waters. It’s again so common for a cheater to only see the overt and undeniable actions that are clear-cut ‘this is an affair’ behavior without understanding all the smaller bites of affair behavior in which they’ve already engaged to get them there.

One might think, after an affair that ended her marriage to her very famous husband, that Kris Jenner would be ever-watchful and very aware and knowledgeable about how affairs start, how they progress, and how horribly they can end. Sadly her choices 20+ years later affected her marriage to Bruce Jenner and the hurt just kept on repeating. Her lack of insight and awareness about her own repeating cheater thinking is, to me, an excellent example of a cautionary tale: You can’t guard against what you don’t truly understand.


It is reasonable and rational to conclude that a cheater who does not change, will not change. An unchanged cheating mindset means that if they started out thinking like a cheater, they probably still think like a cheater.

“Progress is impossible without change; and those who cannot change their minds cannot change anything.”
~ George Bernard Shaw

It’s important to make the distinction between changed behaviors and changed thinking. Jenner’s story is a prime example of a cheater who has changed their behaviors for a considerable time but not their thinking - and when challenging circumstances arose, the cheater thinking easily overtook the hitherto ‘changed’ behaviors.

A cheater who refuses to acknowledge and address their failings is a cheater who expects you to accept them as the person they were on the day they decided to have their affair. If you do, and their choices are detrimental to you, you are simply accepting their maltreatment of you as the cost of your relationship with them.

I believe you deserve better.

So is Once a Cheater Always a Cheater True?

It’s not accurate to absolutely claim that if someone has cheated once that they will cheat again.

Self-exploration, critical review of personal expectations, and addressing an unrealistic world-view is the minimal necessary work for a cheater who wishes to never cheat again, and it can result in lasting and positive change. Examining and addressing issues that may have arisen from their own particular stew of life is part of that work. In truth, there are very few cheaters out there who are truly committed to working towards this nature of personal growth. The experience here suggests that the number of truly successful reconciliations is very few as a result.

If you are reconciling with your cheater, make that reconciliation contingent on their self-motivation to do the work and be the change. And then expect it, measure it, and use it as your yardstick for staying in the relationship. Reconciliation without real and enduring change to the way the cheater views their place in the world risks another affair in the future, as much as it did in the past.

~ Wayfarer



“I'm not a teacher, only a fellow traveler of whom you asked the way. I pointed ahead - ahead of myself as well as you.” ~ George Bernard Shaw

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