Cheating is the most scarlet of all flags

Dating a cheater, whether they cheated on you or someone else, is a bit like buying a used car that’s already broken down once. Sure, it might run smoothly for a while, but you’ll always be listening for that suspicious rattle. Could it work out? Maybe, by some miracle. But the world is full of stories of those who swore they had changed, only to betray their partner again.

Building a relationship with a cheater is not just difficult, it’s also risky. I liken it to a Sisyphean task, constantly striving towards a seemingly asymptotic goal of trusting someone who has displayed untrustworthiness. The effort required to restore trust is immense, and in most cases, it simply isn’t worth it.

To decide to date/reconcile with a cheater, assuming that you are against being cheated on, you are implicitly assuming that they won’t repeat the past and betray you. There are some potential reasons for this:

1. The past cheating was a one-off mistake and they have grown since
2. There were extenuating circumstances
3. The cheating was influenced by factors that are now different

Addressing point 1, if someone has cheated before, whether in a past relationship or with you, they have already proven capable of crossing that line. While people can grow and change, the fact remains that they once justified betrayal, deceit, and selfishness. The reality is harsh: they broke their commitment once, and the only thing that has changed is that they have already been forgiven. That forgiveness itself can embolden them, making it easier to justify cheating in the future. After all, if they were forgiven once, why not again? Why take the risk? No matter how charming, kind, or seemingly remorseful they appear, history has a way of repeating itself. Past behaviour doesn’t always predict future actions, but it is often the only proxy we have.

Regarding point 2, I fully support rehabilitation for most criminals; Many steal or commit crimes because they feel they have no choice. Jean Valjean from Les Miserables stole bread to feed his starving family. But cheating? Cheating never stems from necessity. It is always a choice. Regardless whether it is a dead bedroom, constant quarrels, or just general dissatisfaction, cheating should not be the default option. If someone is unhappy in a relationship, they have an ethical and honourable option: they can end it. They can walk away. Instead, cheaters choose deception, prioritising their immediate desires over the pain they inflict.

For point 3, if we accept cheating is driven primary by the cheater, the biggest factor for infidelity is shared within any relationship a cheater in a part of. You may feel a special connection. However, I’d remind you that whoever the cheater cheated on in the past probably felt the exact same thing. It’s a curious human trait to be overconfident. It’s called the better-than-average effect. Most of us think we’re the exception to the rule—until reality gives us a polite slap. This cognitive bias leads to inflated self-confidence, even though it is statistically impossible for most people to be above average. It’s not necessarily a negative thing, but you should be aware of the inflated risks you face dating a cheater.

Beyond that, a relationship is meant to be a place of trust. Without trust, what’s the point? If you hire an ex-convict, you might take extra precautions to ensure they don’t steal from you. After all, every scrupulous employer will guard against rogue agents regardless of their past track record, even as we support rehabilitation programs. In a romantic relationship however, you shouldn’t have to constantly monitor and second-guess your partner. How do you relax around someone who has already proven capable of such betrayal? How do you avoid becoming paranoid or anxious, checking their messages, questioning their whereabouts, and wondering if they’re lying again? A spouse that has strayed could spark crippling doubt in a partner when they stay out just a bit longer than typical, or perceived secretiveness in messaging. Like Sisyphus, you strain against the doubt while fighting an uphill incline. One slip, and you’re back at the bottom of the hill.

Some people fall into the sunk-cost fallacy, thinking that because they have already invested time and love into the relationship, they should keep trying. But that’s a trap. The past cannot be undone, and dragging yourself through more pain just because you fear “wasting” what you had will only cost you more in the long run. I’m not a huge fan of the Star Wars sequel trilogy, but there is a pretty applicable quote.

“Let the past die. Kill it, if you have to. That’s the only way to become what you were meant to be”. – Kylo Ren

At the end of the day, it’s your prerogative whether to take back a cheater or start a relationship with someone who has cheated before. But I do urge you to carefully assess the risks objectively, and don’t settle for less than you deserve. There are billions of people in the world that have not cheated on you, so why settle for the one person who has?